The PERFECT two-week road trip from Washington DC: Itinerary and tips

Washington DC to Blue Ridge Parkway is a bit far for a short road trip, but you can drive just-as-beautiful Skyline Drive instead.

The Mid-Atlantic is one of the U.S.’s best travel destinations. You can bounce from cities to small towns to national parks to beaches — all within a couple hours’ drive. A two-week road trip from Washington DC might be just the getaway you need this summer.

This Washington DC road trip takes you to some of the East Coast’s greatest cities, national parks, small towns and beaches. It’s affordable — you can camp everywhere except in the big cities. And you won’t have to spend too much time in the car.

Read on for the full DC road trip itinerary!

Note: This post contains affiliate links. If you decide to purchase through these links, I receive a percentage of the sale at no additional cost to you.

FAQ’s to plan the best Road Trips from Washington DC

Whether you're planning a 3-day road trip from Washington DC or a full two weeks, it's smart to map out drive times in advance.
Driving distances on this DC road trip itinerary are short — the longest day in the car will be 3 hours.

I lived in Washington, DC for nearly eight years and Richmond, VA for four years. I want to share all my local knowledge about the region with you — including what not to do. Below are some of the most common questions I get about road tripping in the Mid-Atlantic.

When should you go on a Washington DC road trip?

The DC area has beautiful springs and falls, blazing hot and humid summers, and mild (but still quite chilly) winters.

Autumn is the ideal time for this road trip itinerary. You’ll get stunning fall colors in Virginia at destinations like Shenandoah and Charlottesville, and fewer tourists everywhere else. It’s warm enough to camp through the end of October.

Spring would be my second choice — the wildflowers in Shenandoah are beautiful, but it rains a lot throughout the region. You can camp as early as April. The Appalachian Trail thru-hiker bubble hits Harpers Ferry in June, so the small town gets very crowded at that time.

Believe it or not, I’d rather be on a road trip from DC in winter than summer. Yes it’s cold, but you can snowshoe to White Oak Canyon and you’ll have Harpers Ferry to yourself. Outside of the mountains, snow is unlikely to disrupt your trip.

Summer is the season of last resort. Baltimore, Philly, and Richmond are hot and sticky in July and August. Even the mountains are uncomfortably warm. Crowds are at their peaks. That being said, this itinerary includes plenty of options to cool off in rivers and the ocean.

Shorter alternatives to this road trip itinerary

If you're looking for cheap getaways from DC, it's hard to beat Shenandoah.
Shenandoah is one of the best DC weekend getaways.

If you’re looking for a week long road trip from DC, you can easily modify this itinerary. If you like cities, focus on the first half (through Gettysburg) and then cut down to Richmond. For nature fans, start with Harpers Ferry and continue the itinerary from there.

Many of the destinations on these road trips around Washington DC are also good weekend getaways. You could split this itinerary into a couple shorter trips over the course of a summer if you live in the area.

If you can really only afford a couple days off, my favorite weekend road trips from DC are to Shenandoah and Richmond. Both can be thoroughly explored if you leave on Friday night and return late Sunday.

Mid-Atlantic road trip driving times, gas and accommodation

Assateague, a must-visit on all Maryland road trips, is the only place you have to camp.
Camping on Assateague, the only place on this itinerary without hotels.

I designed this road trip planner so you never have to be in the car for more than half a day at a time. On longer driving days, I include small towns to stop for lunch (so you never have to resort to highway fast food). One of the biggest advantages of a road trip to DC is that everything is super close together.

You’ll have no problem finding gas along most of this itinerary. The one exception is in Shenandoah National Park. Fuel up in Front Royal before hopping on Skyline Drive. From there, you’ll have to make it to Warrenton after you leave the park. The only option in between is the very expensive gas station at Big Meadows Lodge.

This road trip involves a mix of cities and more rural areas, so you’ll use a mix of camping and hotels. Most places where I’ve recommended camping have a hotel option if you prefer it — the one exception is Assateague. You could use a campervan or tent-camp, but I would not recommend an RV for this trip. You’ll need to drive downtown in several cities and parking would be a nightmare with a large vehicle.

What to pack for your road trip from Washington DC

Packing for a road trip is easy -- you don't need to fit everything into a single carry-on!
Feel free to bring a couple suitcases on your road trip if you have the car space. The weather changes on a dime in the Mid-Atlantic.

Packing for a road trip is super fun if you’re normally a minimalist traveler. You don’t need to fit everything into a carry-on — you have all the space you want in your car!

Here are a few of the essentials:

  • Weather-appropriate clothing. Layers are best — the weather changes regularly.
  • Good shoes that you can hike in for the mountains and sandals (with a strap for tubing in Harpers Ferry — no flip-flops).
  • Rain jacket and/or umbrella.
  • Swimsuit and lots of sunscreen.
  • Camping gear if you plan to camp.
  • Cooler with snacks and camping meals.
  • Camera and portable charger.
  • Day-pack that you can take on hikes.
  • Reusable water bottle.
  • Entertainment for the car: a mix of your favorite tunes, audiobooks and podcasts.

Washington DC Road Trip Itinerary – Day One: Baltimore, Maryland

The Domino Sugar sign - a Baltimore icon
You know you’re in Baltimore when you see the Domino Sugar sign.

Start your road trip from Washington DC in the closest major city. While Baltimore is larger than DC, it feels much more low-key. Its neighborhoods have character. It has quirky museums and one of the best aquariums in the country. The food is great. And yet is has a (wildly overstated) reputation for being dangerous and boring. Don’t believe the rumors — Baltimore is a great stop on your mid-Atlantic road trip! Get an early start and aim to arrive in the city by 9 am.

Morning: Inner Harbor and the Baltimore Aquarium

The Inner Harbor is touristy, but it has a lot of the top Baltimore attractions.
Spend your first morning exploring Baltimore’s Inner Harbor.

The Inner Harbor is the center of Baltimore’s tourist kitsch. It has all the usual bad chain restaurants and ice cream stands. But it also has a few attractions worth seeing.

The first thing you’ll notice is the giant floating museum: the U.S.S. Constellation. This ship is the last surviving ship of the Civil War. Today, it’s a museum. It’s not worth paying the entrance fee unless you’re a real history buff, but seeing it from the shore is pretty cool.

But the real reason you’re here is to visit the Baltimore Aquarium, one of the finest in the country. It has everything from a massive shark exhibit to a fully reconstructed Australian rainforest. Other highlights include the enormous jellyfish display, the coral reef with sharks and rays galore, and the exhibit where you can touch rays, flounder, crabs and even jellyfish!

You need about three hours to fully explore the aquarium. Book tickets online in advance so you can skip the line. Adult admission is $40 — I know it seems steep, but it is 100% worth it.

Lunch: Cocina Luchadoras

Grab some cheap tacos at this Fells Point eatery.
This authentic taco joint will fill you up for under $10.

Walk about 10 minutes from the aquarium toward Fell’s Point to find this hidden gem. Cocina Luchadoras has the best, most authentic tacos and Mexican food in Baltimore.

Order from the counter and grab one of the seats in the tiny interior, or sit on the sidewalk if you prefer. Your food arrives within minutes, making this a great quick lunch stop. The tortillas are all handmade and everything is super-fresh.

You’ll spend about $10 on lunch at Cocina Luchadoras. Vegetarians and meat-eaters alike will find something appealing. Check out the menu here.

Afternoon: Baltimore’s best art museums

The Walters Art Museum is in the charming Mount Vernon neighborhood.
You can walk from downtown to the Walters Art Museum, passing through Mount Vernon with its shops and restaurants in old row houses.

DC may have the Smithsonian, but Baltimore gives it a run for its money with two phenomenal art museums. One of them showcases classical and Egyptian art; the other features modern and eclectic works.

Start at the Walters Art Museum in the Mount Vernon neighborhood. This museum is totally free to visit and will keep you occupied for two or more hours. Unless you really like medieval European art, skip those displays and head for the exhibits on ancient Greece, Egypt and Ethiopia. The museum even has a fully intact mummy!

Next, check out the American Visionary Art Museum. You never know what you’re going to find here, but it’s guaranteed to be interesting. When I visited, highlights included a multimedia piece inside a gigantic clown’s mouth and a massive collection of early 20th century toys. Allow two hours to see the whole thing. Admission costs $16 for adults.

Dinner: Afghan food

The naan at Maiwand Grill is amazing.
Afghan food features naan and Indian-like spices, but less heat.

Baltimore’s standout ethnic cuisine is Afghan food. Think Indian with a little less heat, but no less flavor. Pumpkin features prominently, as do cinnamon and cardamom.

The classic spot to indulge in Afghan food is The Helmand in Mount Vernon. The naan is pillowy, the palaw is flavorful. Unfortunately, it’s also a bit pricey and it can be hard to get a table at peak dinner hours. Budget $25 for dinner here.

If you want to stick with something cheaper, check out Maiwand Grill. It’s counter-service but the quality of the food is top-notch. Try one of the combo platters and definitely splurge on the Afghan ice cream. Maiwand is also better for vegetarians than The Helmand. A meal here runs $10-15.

Baltimore practicalities

If you have more time in Baltimore, walk around the historic Fells Point neighborhood.
Fells Point — one of the top neighborhoods in Baltimore for eating and drinking.

Driving time from DC: 90 minutes

Where to stay: There are a bunch of cheap hotel chains around the Convention Center. The Hampton Inn is a good balance of price and quality. Book here.

Safety: Baltimore has a reputation for being dangerous. Parts of the city are pretty dodgy, but everywhere in this itinerary is safe. Be careful around the Convention Center late at night.

Where to park: You can find free street parking in some of the side roads in Mount Vernon. Hotels all have parking lots, and affordable garages abound near the Convention Center. Whatever you do, steer clear of the Inner Harbor unless you want to pay through the nose.

How to get around: You can walk everywhere in this itinerary. Baltimore also has scooters. If you’re feeling adventurous, hop on the free CityLink buses. The routes are not all that useful for tourists unless you’re willing to transfer.

Days Two-Three: Philadelphia, Pennsylvania

The Philadelphia skyline
Philadelphia is one of the great weekend getaways from DC as well as a perfect road trip stop.

Next on this Washington DC road trip itinerary is Philadelphia — one of the most historic cities in the United States. After breakfast in Baltimore and a two-hour drive north, spend two days exploring the Founding Fathers’ legacy.

Explore the Old City

Do a tour of Independence Hall as part of your Philadelphia itinerary.
Tours of Independence Hall take about an hour.

Philadelphia is where the United States was formed. It was the capital in the first years of the republic, before the pro-slavery states of the South objected to locating the seat of government in an anti-slavery state. A stroll around the Old City’s cobblestone streets will give you a feel for what life was like here in the late 1700’s.

Start out with a visit to Independence Hall, where the Declaration of Independence and the U.S. Constitution were signed. Hour-long tours take you through the building and explain its history. Book tickets in advance. The tour is free, but you have to stay with the guide the whole time.

Next, walk across the street to check out the Liberty Bell. Exhibits detail the bell’s history as a symbol for abolishionists fighting slavery. You can also learn how the Park Service has preserved the bell, despite its enormous crack. Honestly the bell itself is rather underwhelming (and impossible to get good photos of), but the exhibit is worth visiting for the historical context.

The Betsy Ross House is next on the agenda. Betsy Ross sewed the first American flag. Her home is now a museum dedicated to the flag’s history and Ross’s role in the American Revolution. It does a good job of contextualizing women’s roles specifically. Admission is $5 for a self-guided tour or $8 with an audio guide.

See also  2 Days in Washington DC: A local's guide to the PERFECT DC itinerary

Finally, walk another few blocks over to Elfreth’s Alley. This historical street is almost perfectly preserved. It’s Philly’s best Instagram spot, with colorful doors, cute gardens, and lots of cobblestones. Just remember these homes are still peoples’ private residences, so please be respectful when taking photos.

If you need a coffee break while exploring the old city, La Colombe Coffee Roasters is Philadelphia’s best third-wave coffee shop.

Happy hour: 2nd Story Brewing

Philadelphia has plenty of good craft beer places, but this one is right around the corner from the Old City. Yes, the neighborhood is touristy, but the beer is fantastic and the snacks are even better.

Duck into the cool air conditioning and order one of the trademark IPA’s. Or go for something a little more adventurous — a Mexican chocolate stout or a key lime blonde. Better yet, try a flight.

Whatever you do, don’t miss the delicious pretzel bites with Philly cheese steak sauce. You can also order burgers and other full meals, and everything looked good, but you have other dinner plans tonight.

Dinner: Classic Philly Cheese Steak at Gino’s or Pat’s

Gino's and Pat's always have lines outside. But the food is worth it.
Gino’s is one of the classic places to try an authentic Philly Cheese Steak.

Now that you’ve had a bit of alcohol, it’s time to indulge in the classic Philadelphia tradition: the cheese steak.

For those who aren’t familiar, cheese steaks are sandwiches with sliced or chopped steak and cheese wizz, served on a hoagie-like bun. You can add toppings like onions, peppers and mushrooms if you like. It’s all horribly unhealthy and extremely delicious.

Gino’s and Pat’s are two of the original cheese steak shops. They set up shop across the street from each other in a South Philadelphia neighborhood. They dish out more or less equal cheese steaks to hungry tourists and buzzed locals.

You can order a few varieties of sandwich, but be prepared to get the stink-eye if you go with anything other than Cheese Wizz. Sandwiches run $10-12.

If you’re a vegetarian, this experience is entirely skippable unless you want fries for dinner. You can find vegan cheese steaks all over the city instead.

Street art

One of the many street art works along the MuralArts tour.
Self-guided walking tours through downtown take you past the city’s political and historical murals.

Now that you’ve seen what the Old City has to offer, spend your second day in Philadelphia exploring its more modern areas. Before you get started, drop in to Luna Cafe for a delicious and cheap breakfast.

Hop on the subway to City Hall and spend a few minutes exploring one of the U.S.’s most memorable government buildings. You can walk through the courtyards and visit the tourist information office inside.

Next, walk across the street and check out the “Love Park.” This is another must-visit Instagram spot in downtown Philly.

Spend the rest of the morning on a self-guided walking tour with MuralArts. You can download a map from their website. The walks are about a mile long and take you past street art that leans into the city’s history and politics beyond the basics.

Lunch: Reading Terminal Market

Reading Terminal Market has fresh produce, souvenirs and food stalls.
If none of the food stalls look appealing, pick up some produce at Reading Terminal Market and build your own picnic.

By now it’ll probably be lunchtime, so pop over to Reading Terminal Market. This enormous public market has been running out of the same building downtown since the late 1800’s. It prominently features Amish vendors.

The market has everything from fruit and veggie vendors to farm-fresh cheese to coffee roasters to souvenirs to take-away food stalls. You can eat at the counter at a few of the restaurants, but on a crowded day, you’ll need to grab your food to-go and find a table in the central food court area.

Spend half an hour perusing the market before deciding on a lunch spot. To help narrow your options: Dutch Eating Place’s apple dumplings are to-die-for, and save some room for Basset’s Ice Cream.

Afternoon: Rocky steps and Eastern State Penitentiary

Once you’ve filled up, take the long walk down Benjamin Franklin Parkway. Along the way, you’ll pass flags from every country in the world lining both sides of the street. Your destination is the iconic steps from the movie Rocky — another classic Instagram spot. Here you’ll find a few of Philadelphia’s best museums, but you won’t have time to visit them. Instead, continue into the Fairmount neighborhood to Eastern State Penitentiary.

Eastern State Penitentiary’s claim to fame is that it once housed Al Capone. More broadly, it was one of the most feared prisons in the U.S. during its heydey. Today it’s a museum focused on the criminal justice system.

Your admission ticket includes an audio guide that takes you through a few of the main cell blocks. You’ll learn about the history of the American penal system and why Eastern State Penitentiary was one of the most feared institutions in the U.S.

After you cover the main tour, you can branch off and explore more on your own. Some of the exhibits touch on inequity in the criminal justice system, how women are treated in prison, and the juvenile detention system. You could spend hours listening and reading in these exhibits.

Admission to Eastern State Penitentiary costs $15 if you purchase tickets online in advance (buy them a few minutes before you arrive or you’ll pay an extra $2 at the door per person). You can take photographs throughout the facility, and the dim lighting and eerie corridors lend themselves to great photos.

Dinner: Hip City Veg

The veggie burgers at Hip City Veg taste just like the real thing.
Hip City Veg in Philadelphia is a vegetarian’s heaven.

You could spend a small fortune of your budget for this road trip from Washington DC on a night out in Philly. Save yourself a few bucks and stick with a casual meal instead.

Hip City Veg is an all-vegan fast-casual eatery. It has a few locations throughout the city, including one right near City Hall.

Literally everything on the menu is awesome. Even meat eaters will have no problem finding something that appeals to them. But the biggest treat is the vegan “chicken” — it’s the only mock-chicken I’ve had that even comes close to the real thing. Delicious house-made buffalo sauce is the go-to sauce. And definitely don’t skimp on the sweet potato fries.

Dinner at Hip City Veg costs around $10.

Philadelphia practicalities

Philadephia is one of the best short trips from DC.
Philly is super walkable — but you can always hop on the SEPTA if your feet need a break.

Driving time from Baltimore: 2 hours

Where to stay: The best budget pick is Apple Hostel. It’s central, clean, on a quiet side street, and has great facilities. Staff organize activities like bar crawls and walking tours a few times a week.

Safety: I’ve always felt very safe in Philadelphia. There are some dodgy neighborhoods for sure, but you’re unlikely to visit them as a tourist.

Where to park: Parking in Philly is pricey. Your best bet is the Ritz East parking lot, which charges $22 for every 24 hours.

How to get around: Philadelphia is very walkable — you can walk everywhere in this itinerary. But if you want to get around more quickly, the weather is bad, or you can’t walk 1-2 miles at a time, take advantage of the outstanding public transportation system. The SEPTA subway and trolley network can get you within a couple blocks of any destination downtown or in the Old City. Single fares cost $2.50, but if you plan to use it a lot, invest in a $9 one-day-unlimited-rides card. Not all stations are accessible to people with limited mobility.

Day Four: Philadelphia – Gettysburg – Harpers Ferry

It only takes about two hours to drive from Philadelphia to Gettysburg.
Gettysburg Battlefield — the site of the turning point of the Civil War.

Today, it’s time to escape the big coastal cities and head to some of the Mid-Atlantic’s most prominent historical sites. Your destination is Harpers Ferry, WV. But the historic battlefield of Gettysburg makes a good lunchtime stop. Get on the road by 9 am — this is one of the longer driving days on this road trip from Washington DC.

Morning: Gettysburg Battlefield

You can visit Gettysburg on your own -- no need to take a tour. Signs and maps from the visitor center explain things.
Visiting Gettysburg is a must for history buffs.

The Battle of Gettysburg is considered by many historians to be the turning point in the U.S. Civil War. The three-day battle marked Confederate General Robert E. Lee’s second failure to invade the north. It was also the bloodiest battle in the war, killing more than 50,000 people — nearly a third of the two armies. Today, you can visit the battlefield to learn more about the Civil War and the battle itself.

Most people visit independently — you can pick up a brochure at the Visitor Center. (Or rely on the history buff in your travel group — a.k.a. your dad — to tell you all about it.) If you want a little more context, the Visitor Center and museum have a few good displays. You can also choose to hire a guide if you really want to dig deep. The battlefield is free to visit and takes about two hours for people with a casual interest in history. You could spend half a day or longer here if you really want to learn more.

After you explore the battlefield, grab a quick lunch in the cute town of Gettysburg. Gettysburg Baking Company is a great option — it has a handful of sandwiches, soups, and deli items for affordable prices. Top it off with a pecan sticky bun or fresh-baked cookie.

Afternoon: Harpers Ferry

Harpers Ferry is a historic site where you can visit replicas of old shops and houses.
One of the old buildings in historic Harpers Ferry.

Like Gettysburg, Harpers Ferry is steeped in 19th-century history. It’s strategically situated on the Potomac and Shenandoah Rivers, at the intersection between Virginia, Maryland and West Virginia, and alongside the Chesapeake & Ohio Canal. It was the site of John Brown’s Raid and a military football during the Civil War.

Today, the National Park Service has preserved the historic center and turned it into a living museum of sorts. You can visit model shops and homes, and even go to a traditional candy store.

Spend the afternoon exploring the town center and learning about the history. Don’t miss the old cemetery (which the Appalachian Trail crosses through) and John Brown’s Fort. All the attractions in this area are free.

Dinner: The Canal House

Harpers Ferry’s dining options are geared toward tourists, so you can easily spend a small fortune on dinner in this town. But the Canal House Cafe has an affordable sandwich menu (and a much less affordable main menu) where you can grab dinner in homey surrounds for cheap.

Settle in around the roaring fireplace at one of the handful of tables in the dining room. Chat with the friendly staff while they take your order. You can’t go wrong with the pulled pork or blackberry grilled cheese, but you can find veggie options as well. All sandwiches and burgers are in the $8-15 range.

The Canal House is right on the main strip, so you can easily walk from your accommodation. After dinner, head to your hotel for an early night (or enjoy some wine on the balcony). Harpers Ferry doesn’t have much in the way of nightlife.

Day Five: Hiking and Tubing in Harpers Ferry

Harpers Ferry is one of the favorite weekend trips from DC. Today, spend the morning in the mountains and the afternoon on the river to get a taste of what this town has to offer. Pack a picnic lunch today so you don’t have to spend time stopping in town.

Morning: Hike to Maryland Heights Overlook

Maryland Heights Overlook is one of the best hikes in Harpers Ferry.
The view from Maryland Heights Overlook.

Most hikes in Harpers Ferry take you to historical sites rather than scenic mountain views. But the hike to Maryland Heights Overlook is the best of both worlds. This short, moderate trail takes you to the best view over the town and the rivers and hills beyond.

Start in the center of town and follow the C&O Canal Towpath 0.3 miles. Here you’ll see the Maryland Falls trailhead. It’s a straight 2.25-mile shot (complete directions here).

The trail starts out wide and moderately steep before narrowing and leveling off about a mile in. It’s extremely well-maintained and you certainly won’t be the only person on it, but it’s not overwhelmingly crowded either.

See also  Hiking the Subway in Zion National Park: The Bottom-Up Route

You’ll see a couple social trails on the way up, which take you to views over the Potomac. The final turnoff takes you half a mile down for the iconic overlook. This is a great snack stop.

If you like history, consider adding the Stone Fort Trail loop on your way back. It adds a little less than two (flat) miles to your hike and takes you past a crumbling Civil War fort.

Otherwise, go back the way you came for a total of 4.5 miles. It took my family about two hours.

The Appalachian Trail Conservancy and NPS visitor center staff rate this hike “difficult.” But they’re overcorrecting for the flat surrounding areas. If you compare it to hikes in more mountainous regions like New England, Southern Appalachia, or out West, it would earn an “easy-moderate” rating.

Afternoon: White-water tubing on the Potomac

Tubing in Harpers Ferry is a popular day trip from Washington DC.
You’ll go under old railroad bridges like this on the whitewater tubing route.

Harpers Ferry offers one of the most adventurous river trips in the region — the opportunity to go tubing through Class III whitewater rapids! It’s not as scary as it sounds (you won’t flip over, nor will your beer cooler), but it’s definitely more of a thrill than the usual flat-water tubing you might have done before.

The trip starts a couple miles out of town. You get in the water and immediately paddle to the opposite river bank — the most athletically intense part of the whole experience. Then, you sit back, relax, and enjoy the thrills of riding down fast-moving rapids. You get some nice long breaks between rapids to give you time for a drink or a snack and enjoy the scenery.

The whole river run takes anywhere from 3-6 hours, depending on how much you paddle vs. how much you let the river determine your speed. At the end you take a short shuttle back to your car. You can change into dry clothes at the tubing company’s base.

For safety reasons, you may not go on the river barefoot or wearing flip-flops — you must wear shoes with a strap. I recommend bringing dry shoes to change into at the end of the day, in addition to clothes. And don’t forget sunscreen — there’s no shade on the river!

You can book your whitewater tubing adventure here. It costs $23 on weekdays and $33 on weekends. You can rent an inflatable cooler or a float to attach your own cooler to for $10. If you’re traveling with kids, note that only people age 12 and older can do the whitewater route (young kids can still go flatwater tubing a couple miles away).

After tubing, grab dinner at whatever spot in town looks appealing. You’ll be too tired to go hunting for the perfect spot.

Harpers Ferry practicalities

You can walk to most of the historic sites around Harpers Ferry.
Harpers Ferry is managed by the National Park Service.

Driving time from Philadelphia: 3.5 hours, including the detour to Gettysburg.

Where to stay: Harpers Ferry is a great spot for a splurge on a boutique B&B. I like Ledge House Bed and Breakfast. The owner makes fantastic eggs Benedict in the mornings and you can see the trains rumbling through town. A cheaper option would be to camp — KOA is within walking distance of town.

Safety: Harpers Ferry is very safe.

Where to park: NPS manages a handful of parking lots around town. They provide free shuttles to the center. Don’t try to drive into the center unless your accommodation has parking. If you visit on a weekday in off-season, you may be able to find parking on a side street within the center (but I once drove around for an hour looking for a space only to give up and end up in an NPS lot).

How to get around: The town center is about 3 blocks x 5 blocks, so you can walk everywhere. You’ll need your car to reach the tubing company.

Days 6-9: Shenandoah National Park

My favorite stop on this itinerary: Shenandoah and Skyline Drive.
Road trip pro tip: Check your lights after you drive on Skyline Drive. It’s easy to forget to turn them off after going through the tunnels.

Ahhhh, Shenandoah. One of my favorite parks in the entire U.S. park system. Where you can wake up above the clouds in the Blue Ridge Mountains, hike to hidden waterfalls, and drive to Skyline Drive’s epic overlooks. Three days is the bare minimum to explore this epic national park.

Shenandoah National Park is split into northern, central and southern districts. The northern district, near Front Royal, and the southern district see very few visitors. Most of the crowds stick to the central district, but that’s because this district has most of the park’s best hikes and views.

Rather than giving you an exact itinerary for these three days, I’ll lay out a few activities that you can mix and match however you like.

Go hiking

Sunrise hikes in Shenandoah National Park are epic.
You can hike to the summit of Old Rag for sunrise — just make sure you go up the fire road. The rock scramble isn’t safe in the dark.

Shenandoah has the Appalachian Trail, waterfalls galore, and one of the region’s only balds. You can find rewarding hikes to suit every experience level.

I have an entire post on the best hikes in Shenandoah National Park, but here are a few you should not miss:

  • Little Stony Man: Short, easy hike to a great view
  • Lewis Falls Trail: Steep going down, but you can take a longer and more gradual route back up
  • Big Meadows – Rose River Loop – Dark Hollow Falls Loop: A little-visited overlook, beautiful river, and two gorgeous waterfalls. Not crowded.
  • Hawskbill Mountain: The highest peak in Shenandoah
  • Big Devil’s Stairs: Very remote hike to a gorge along the park boundary. You likely won’t see another person the whole time. Great autumn hike.

And then there are my two all-time favorites, which deserve special mention. The first is Old Rag — the hike everyone will tell you to do in Shenandoah. The summit is a rocky bald with panoramic views. But the reason everyone loves this hike is the long and intense rock scramble to the summit. It’s not for the faint of heart (or for parents with small children, and definitely not for dogs). You only have to scramble one way before taking the fire road back down. Crowds near the summit mean you can experience waits of up to an hour in some sections during peak weekends.

While Old Rag is beautiful, it loses to White Oak Canyon in my list of most-beloved Shenandoah hikes. White Oak Canyon is the harder hike, because you spend the first 3/4 of it going downhill, only to need to climb back up on the way back out. The highlights are the seven waterfalls along the way.

The classic 8-mile hike descends the Cedar Run Trail. Come back up the White Oak Canyon trail and turn left on the fire road after the final waterfall. A shorter and easier alternative starts at Limberlost and descends the White Oak Canyon trail as far as you want to go, before you go back the way you came. The most epic variation is a shuttle hike (i.e. you need two cars), and runs from Hughes River Gap to Crescent Rock Overlook — crossing five streams (including one unmarked, wide river crossing) and ascending 1,500 feet in half a mile at the end of an 11-mile hike.

Cool off at the natural water slide

Cool off in White Oak Canyon's many waterfalls and swimming holes.
The White Oak Canyon hike includes a waterfall that has a natural water slide.

This one’s great for families. Shenandoah has a few good swimming holes. But you can do even better to cool off on a hot day.

The rock formations at Cedar Run Falls are perfect for creating a natural water slide. Jump in at the top and slide down the rock face into the pool below.

You can, of course, take a dip in the swimming hole if you don’t feel like sliding around. But it’s overall very safe and not all that crowded on weekdays.

Cedar Run Falls is the first waterfall on the Cedar Run Trail — about a mile in. The hike is steep, so you should wear proper shoes and clothes (i.e. not flipflops and your swimsuit).

Walk around the big meadow

Don’t feel like hiking, but still want to get outside? No problem! An easy walk starting from Big Meadows Lodge will give you a glimpse into Shenandoah’s biodiversity.

You can’t miss the big meadow, on the east side of Skyline Drive across from the gas station. A flat, paved path takes you far into the bush. Signs explain the flora and fauna.

This is also a fantastic sunrise/sunset spot if you want something a little different than mountain vistas.

Watch wildlife

The deer in Shenandoah National Park will approach very close to you.
Deer are everywhere in Shenandoah.

Shenandoah has well over 300 species of animals. With three days in the park, you’ll have an opportunity to spot lots of them.

You’ll surely spot deer on your visit to Shenandoah — they’re everywhere. They’re also surprisingly friendly. Don’t be surprised if they let you come within a few feet.

You have to be a little luckier to spot the gray foxes and red foxes. Your best bet is dawn and dusk in the meadow.

The one animal everyone wants to see is a black bear. I’ve seen three at campsites in Shenandoah, two along the side of the road, and two on hiking trails in over two dozen visits to the park. Dawn and dusk are the best times. See the ‘safety’ section below for details on hiking in bear country.

Birds are another highlight of Shenandoah. The park has 196 species. Get the checklist here.

Shenandoah National Park practicalities

When hiking in bear country, talk or sing on the trails so you don't surprise a black bear.
Black bears aren’t really a safety risk — they’re quite shy. Just make noise to let them know you’re around.

Driving time from Harpers Ferry: 2 hours

Where to stay: Camp at Big Meadows Lodge. You’ll get all the benefits of a central location, it’s affordable, and you can choose between cooking over the campfire or eating in the cozy lodge restaurant.

Safety: Skyline Drive is the main road through the park. Stick to the posted speed limits — wildlife and cyclists come out of nowhere on the hairpin turns. Make lots of noise when hiking to let bears know you’re around — black bears aren’t aggressive unless you surprise them. If a bear approaches your campsite, bang pots and pans together while slowly backing away. Hang all food at night or store it in a locked vehicle.

Where to park: All hikes and attractions have ample free parking areas, with the exception of Old Rag. You may have to pay a small fee to park in an overflow lot on private property here.

How to get around: Driving is the only realistic way to explore Shenandoah National Park.

Days 10-11: Richmond via Charlottesville

How far away is Washington DC from Richmond? Under two hours, but few DC locals have visited.
Richmond is an underappreciated city, but it’s a perfect stop on this road trip.

Once you’ve gotten your fill of nature, it’s time to head back to the city. The next stop on this Washington DC road trip is Richmond.

Today you’ll drive through some of the most beautiful countryside in the region — rolling hills, endless farms, and cute vineyards abound. Charlottesville, a charming college town and the home of Thomas Jefferson’s estate, provides the perfect opportunity to break up your trip.

I went to college in Richmond, so my recommendations there are based on local knowledge.

Day 10 Morning: Drive to Charlottesville and go wine tasting or apple picking

The vineyards around Charlottesville offer wine tastings in beautiful surroundings.
Jefferson Vineyard has a lovely patio where you can look at the mountains during your tasting.

Get on the road by 10 am for the one-hour drive to Charlottesville. Let the time of year dictate your destination in town.

If it’s spring or summertime, head for one of the area’s wineries. That link provides you with a number of options, but I’ll save you the decision-paralysis and just recommend Jefferson Vineyards, where Thomas Jefferson himself once produced wine.

Tastings cost $12 for the basic or $25 to include some of the premium wines. You get to keep your glass. After you’ve tried everything, grab a glass of your favorite and head out onto the vineyard grounds for a shady spot. You can bring your own picnic snacks or buy cheese plates and simple sandwiches on-site. The views out to the Blue Ridge Mountains are lovely.

Alternatively, in fall, head for Carter Mountain Orchard for apple and pumpkin picking. This hilltop orchard offers more varieties of apples than you will have heard of in your life. When you arrive, you’ll receive a guide explaining what’s ripe and how to use each type of apple (i.e. baking, eating, cooking). Wandering around is free, and you can definitely get away with snacking on a few apples while you pick. The apples themselves start around $8 for a half-peck.

See also  Easy hikes in Zion National Park: Seven amazing trails

After you’ve picked your fill, head to the country store and pick up a package of their legendary apple cider donuts and hot apple cider. You’ll have a sugar hangover for days, but it’s so worth it!

Optional stop: Visit Monticello

Monticello was Thomas Jefferson's plantation. Now it's a museum.
Monticello has a complicated history and problematic relationship to slavery.

If you have a special interest in history, at this point in the road trip itinerary you can extend your stop in Charlottesville to visit Thomas Jefferson’s home, Monticello.

The mansion is a classic Southern estate, with all the racist legacies that go along with it. (I.e. this is not a place to pose for cute Instagram photos.) If you choose to visit, the best option is the self-guided tour through the mansion followed by a walk through the gardens and grounds.

The ticket price for Monticello is pretty steep — at $29, you have to really care about the history for it to be worth it. Allow at least two hours to visit.

On your way out of Charlottesville, stop for lunch at Wayside Chicken. You won’t find a more delicious meal for under $6 anywhere in the South.

Day 10 Afternoon: Drive to Richmond and have dinner

Edo's Squid is the best Italian restaurant in Richmond.
It looks sketchy, but Edo’s Squid is one of the best restaurants in Richmond.

By the time you leave Charlottesville, it’ll probably be 2 or 3 pm. The drive to Richmond takes another hour. So you’ll arrive just in time for happy hour or an early dinner.

One of the best places in town for pre-dinner drinks is Capital Ale House downtown. It has dozens of local and regional beers and a selection of craft beers from around the country. Truly the best beer list in the city.

The food at “Cap Ale” is good too — go for the giant soft pretzel. But if you want something a bit more substantial for dinner, make your way over to the VCU campus and drop in to Edo’s Squid. Yes, this place looks sketchy AF from the outside. Yes, you will think you’re walking into a serial killer’s lair on your way up the stairs. But it’s still the best Italian food Richmond has to offer, and for very reasonable prices ($11-20 mains).

Day 11 Morning: Breakfast, Canal Walk and Belle Isle

A view of Richmond from Belle Isle.
Belle Isle has swimming, walking trails, and great views of downtown Richmond.

Richmond has SO many great breakfast options, it’s hard to choose one. So don’t! Pick up pastries from the city’s best bakery and coffee from its most charming cafe.

Subrosa, in the revived Church Hill neighborhood, is pretty much the greatest bakery on the planet. The pastries are perfect. Flaky, perfect blend of sweet and savory, big enough to fill you up without feeling gross, and above all, fresh. You literally can’t go wrong here, so you might as well try them all. If they have bear claws when you visit those are a must. (Note many of their pastries have ham or salami in them, so vegetarians should ask about ingredients.)

Once you’ve got your pastries, drive to Shockoe Slip and grab one of the sidewalk tables at Shockoe Espresso. Grab a cappuccino or iced coffee and a board game from inside. This is a great people-watching spot on a quiet, historic street.

I know, you’re not just in Richmond to eat. So next it’s time to head to the Canal Walk. You can walk here from Shockoe Espresso — it’s just a few blocks away.

The Canal Walk goes, well, along the city’s old canals. You’ll see the old locks and weave between historic tobacco warehouses. The architecture is great, but even better is the incredible street art you’ll see along the way. My favorite is the giant legs sticking out of the wall!

Follow the Canal Walk all the way to the James River and keep going in the direction of Belle Isle. This river island has a dark history — it housed a slave and POW prison during the Civil War. You can follow a history trail marked with clear signs around the perimeter (about an hour).

But if there’s one thing native Richmonders love to do, it’s reclaim the city’s Confederate history and turn monuments of oppression into beautiful public spaces. So no one will be offended if you skip the history tour and instead enjoy the natural scenery. Find a sunny spot to take in the river views, sunbathe, or swim (the safest swimming spots are on the opposite side of the isle from the bridge).

Afternoon: Lunch and Carytown

Plan 9 is Richmond's best record store.
Don’t miss a trip to Plan 9 when you walk around Carytown.

Dry off and walk back to Shockoe Slip to pick up your car. Drive about two miles north into the heart of the Fan district — where the streets ‘fan’ out as you travel west. This charming neighborhood was my home for four years and is still my favorite part of the city.

Stop for lunch along Lombardy St. at longtime favorite Kuba Kuba. There will probably be a line, but it’s 100% worth it. The affordable sandwiches and mains are filling and lick-your-plate delicious. Don’t forget to try the Cuban coffee. You can walk the rest of the way into Carytown from here, or drive the remaining mile west.

Carytown is Richmond’s eclectic shopping strip. These are a few of my favorite spots:

  • Plan Nine Music: Named for Plan 9 from Outer Space (possibly the worst cult sci-fi movie ever made), this place is a treasure trove for music lovers. Find old-school records for $1 in the basement.
  • Bygones Vintage Clothing: Try on a 1920’s cocktail dress or a mask from a legit masquerade ball.
  • Galaxy Diner: Stop in for fried Oreo’s while you shop.
  • World of Mirth: The world’s coolest toy store that pretends it’s for kids but has secret hidden gems for adults. Try to find the Jesus action figures.
  • Goodwill: This branch features tons of vintage clothing. Great spot to find the same stuff as Bygones for a fraction of the price.
  • Chop Suey Books: Wall-to-wall used books in the $5-8 range.
  • The Byrd Theater: Second-run movie theater and centerpiece of RVA culture. Watch a typical film for $4, or go to one of the silent movie specials where a live organist accompanies the film. Organ performances at every Saturday evening show.

If you have some extra time before dinner, pop into the Virginia Museum of Fine Arts. It’s free to visit and while it’s a bit heavy on 19th century hunting portraits, the upper floors have some interesting modern exhibits.

Dinner: Buz and Ned’s Barbecue

Buz and Ned's has the best barbecue in Richmond.
Don’t miss a pulled pork sandwich from Buz & Ned’s on your Richmond trip.

Once you’ve worked up an appetite from walking and shopping, grab your car again. It’s a short drive to tonight’s dinner spot: Buz and Ned’s Barbecue on Boulevard St.

This old-school barbecue joint is no-frills, but you can get an enormous meal for $10. The meat is tender and flavorful (go for the pork), the service is friendly, and the hush puppies are the perfect crispy-chewy texture. If you’re not sure how to order, go for one of the full meals. It’s the most authentic barbecue you’ll find on this road trip from Washington DC.

While Buz and Ned’s looks close to Carytown on the map, it’s not a great idea to walk here unless you know the area. The couple blocks between Broad St. and the Flying Squirrels stadium are dodgy.

Bonus: First Fridays in Richmond

If you timed your visit to Richmond on the first Friday of the month, don’t miss the chance to explore one of the East Coast’s best art walks. Two gallery-dense sections of the city open to the public each First Friday. You can visit any of the galleries for free and purchase pieces directly from the artists.

The first section runs through the Fan along Main St., concentrated around Lombardy. This area is heavy on more traditional works — lots of painting and photography. A couple of these galleries also showcase works from VCUArts students.

The more interesting area is along Broad St. downtown. You’ll find lots of contemporary artists on display here, along with street performances like music and fire dancers. ADA Gallery is a good bet for multimedia, and Anne’s shop has always has fun and affordable works to take home.

Richmond Practicalities

One of the things that makes Richmond so great is its old tobacco warehouses converted into shops and apartments.
An old tobacco company office in Richmond.

Driving time from Shenandoah National Park: 3 hours

Where to stay: Richmond has my favorite bed and breakfast anywhere in the world — the Museum District Bed and Breakfast. The host is super-friendly and makes a breakfast to remember. Bonus: Free wine and cheese on your balcony every day! If you want to save money, stay at the HI Hostel downtown instead.

Safety: Richmond’s crime rates have improved dramatically over the last decade. The areas I cover in this itinerary are all very safe. Don’t wander south of the James River unless you know where you’re going, steer clear of Broad St. north of the VCU campus, and avoid Grace St. on weekend evenings, but otherwise you should be fine. Your biggest risk is swimming in dangerous rapids at Belle Isle.

Where to park: You can usually find free street parking in Richmond if you’re willing to circle the block a few times. Secret free parking spots can be found on Byrd St. around the corner from Shockoe Espresso in the Slip, on Franklin St. downtown, and on Kensington, Hanover, Stuart and Boulevard Streets in the Fan. In Carytown you’ll need to park on Boulevard and walk or try to snag one of the handful of spots in the plaza with Can Can.

How to get around: A mix of driving and walking. Richmond has a bus system, but it’s not practical for short-stay visitors to figure out the routes. Renting a bicycle is also a great option, but it’s not much fun to climb the hill between Shockoe and downtown.

Days 12-14: Assateague National Seashore

Assateague is one of the best beaches near DC, and it has wild horses.
The wild horses of Assateague Island.

On this road trip from Washington DC, you’ve been to cities, historical sites, and national parks. Now, it’s time to hit the beach.

Before you leave Richmond, grab a quick breakfast from Lamplighter Cafe, or linger over brunch at The Daily.

Assateague National Seashore is the best beach in the region. This narrow barrier island has miles of untrammeled coastline. Plus: wild horses!

Spend the last couple days of your DC road trip relaxing and having barbecues on the beaches and swimming in the sea. There isn’t much to do on the island besides go to the beach and walk or ride a bike along the flat paths.

Be extra-careful with your food here, since the horses are attracted to it (please don’t feed them!). Additionally, Assateague is legendary for its mosquitoes, so bring plenty of bug spray.

Assateague Practicalities

You can walk or ride bikes everywhere on Assateague Island
A boardwalk on Assateague Island.

Driving time from Richmond: 3.5 hours

Where to stay: Camp at the federally managed campground. Note that very few campsites have shade — the island simply doesn’t have very tall trees.

Safety: Assateague is very safe.

Where to park: Park at your campsite.

How to get around: The island is only two miles wide at its widest point, so you can walk or bike pretty much everywhere.

Last day: Drive back to Washington DC

Drive to Washington DC from Assateague to end your road trip.
The drive to DC from Assateague takes about three hours.

It’s about a 2.5-hour drive back to DC from Assateague Island. Allow extra time for traffic if you have a flight out.

I hope this DC road trip itinerary gives you some ideas for your next close-to-home getaway!

Like this post? Pin it!

Plan the perfect road trip from Washington DC! One of the best USA road trips is in the Mid-Atlantic. This road trip itinerary includes places to go, the best restaurants along the way, drive times, and other road trip essentials. #usa #travel #roadtrip

Read more about the USA here

3.5 2 votes
Article Rating
Subscribe
Notify of
guest

This site uses Akismet to reduce spam. Learn how your comment data is processed.

19 Comments
Oldest
Newest Most Voted
Inline Feedbacks
View all comments
Krista
3 years ago

Wow this road trip looks incredible!

Umiko
Umiko
3 years ago

I like your itinerary since it has information on some cities and places that I wanted to see. I really want to go to Shenandoah NP, Harpers Ferry, and Gettysburg. Seems like I got pretty much all of the basic information needed for first timers. We stopped for an hour at Harpers Ferry last Christmas Break (it’s not enough at all!) and drove through Shenandoah. I know I have to come back.

MacKenzie
3 years ago

This list is absolutely incredible. It must’ve been a huge labor of love! There are quite a few places I’ve been meaning to go, like Shenandoah, and some I hadn’t considered, like the Seashore! Thank you for all these ideas.

Vaisakhi Mishra
3 years ago

This is indeed the perfect road trip from Washington DC! I absolutely love Philly and Monticello and Philly old town is one of my favourite sites in the entire US! I am yet to visit Harpers Ferry, but am definitely adding to to my east coast list after this post of yours!

Lisa Shehan
3 years ago

OMG – this is so helpful!! Using this for a future roadtrip!

Agnes
3 years ago

Love that you included Assateague. I used to live out in DC and then Maryland, and that was a weekend trip for us one summer…mainly because a friend of mine loved the children’s book Misty of Chincoteague. 🙂 Great list!

Savannah
3 years ago

This is incredibly detailed and made me so much more excited to move to Philadelphia in a couple years and explore all of these places!!!

Arielle Kurtze
3 years ago

I love this road trip! So much to see and do within driving distance of Washington DC. I would highly recommend this as a great vacation and people can follow your advice vs spending weeks and weeks trying to come up with a schedule which probably wouldn’t be half as good. Loved your photos and thanks for sharing!

Michael Baker
3 years ago

Such a detailed guide. Thanks for sharing! Perhaps this fall my family and I will go to the Washington DC. Awesome photos!

Linn
Linn
3 years ago

Seems like the perfect road trip! I hope I get to go one day and I will definitely use some of your tips:)

19
0
Would love your thoughts, please comment.x
()
x