14 Day Trips From DC to Explore the Mid-Atlantic Region (2024)

Located in the heart of Virginia’s beautiful Blue Ridge Mountains, the Roanoke Valley promises small-town charm with big city vibes. Accessible via Amtrak or the oh-so-scenic Blue Ridge Parkway, the area is home to one of the most breathtaking points on the Appalachian Trail: McAfee Knob, located 3,197 feet atop Catawba Mountain. After a day’s long hike, grab a pint at one of the many area breweries likeDeschutes Breweryand shop for antique relics at the cavernousBlack Dog Salvage.

If you do just one thing... Be sure tograb a scoop atPop’s Ice Cream and Soda Bar on your way back home.

Want to stay overnight? Book a room at Hotel Roanoke.

This small town in West Virginia is en route to Lost River, a bucolic retreat that draws a large gay population. Once a pit stop, it is now slowly becoming a destination in its own right thanks to a concentrated effortby its entrepreneurial residents.Drop by Lost River Trading Post, a mercantile-meets-art gallery filled with locally made goods, and don’t forget to swing by Wardensville Garden Market and Bakery,a non-profit farm market that sells from-scratch goodies.

If you do just one thing…Enjoy Bluegrass in the Barn, a monthly live music celebration at Capon Crossing Farm.

Want to stay overnight? Book a room at Firefly Inn.

Nautical enthusiasts will fall hard for this seaside town in Maryland. Don’t overlook theChesapeake Bay Maritime Museum, a favorite among locals that's knownfor its stunning sunset vantage point. Affordable cruises and water activities are also available through the museum. Continue your adventure atLyon Distilling(temporarily closed), which serves delicious rum and whiskey made on-site, andJustine’s Ice Cream Parlor‚ a sweet finish to the sun-filled day.

If you do just one thing… Take a cruise down the Miles River in a replica 1930s steamship with Patriot Cruises. You’ll get both great views of the city and an entertaining overview of the history and sites.

Want to stay overnight? Book a room at George Brooks House.

Thrill seekers flock to Harpers Ferry for the chance to experience adrenaline pumping adventure sports, including white water rafting and tubing in the Potomac River.Harpers Ferry Adventure Center is one of the most trusted rental companies in town. For those who aren’t quite as intrepid, a visit to the cobblestone streets and charming architecture throughout the Lower Town area might sound like a more attractive daily activity.

If you do just one thing…Walk through the 20 miles of nature trails at Harpers Ferry National Historical Park.

Want to stay overnight? Book a room at Light Horse Inn.

For the equestrian set, there’s no better day trip destination than Middleburg. The posh town in Loudoun County is home to upscale horse farms and more than 30 wineries. You’ll also find world-class golf courses and countryside resorts likeSalamander Resort and Spa, a luxe escape with a gourmet restaurant, putting green, equestrian center, and views for days.

If you do just one thing… Visit during theMiddleburg Film Festivalin October, a celebrated event that draws some of the entertainment industry’s major players.

Want to stay overnight? Book a room atthe Salamander Resort and Spa.

Accessible via train, Fredericksburg is a quick trip down memory lane. Here, you’ll find poignant Civil War battlefields and tons of George Washington-related history, including the homes of his mother and sister. Stroll down Caroline Street for a glimpse of the city’s many clothing and art boutiques (we love Ponshop) and antique shops. Hungry? Foodeis a cult favorite andBenny Vitali’s has some of the best pizza in town.

If you do just one thing… Grab frozen custardCarl’s, a retro ice cream shop that’s been satisfying sweet tooths since 1947.

Want to stay overnight? Book a room at The Richard Johnston Inn & 1890 Caroline House.

Richmond is rich in southern hospitality, delicious restaurants and historic sites. Luckily, it’s only a quick train ride away. L'Opossum is a hip French spot that’s worth checking out. Don’t miss out on strolling through Carry Street, which is packed with adorable vintage shops, clothing stores andother fun destinations.

If you do just one thing…Visit theByrd Theater, a historic movie house.

Want to stay overnight? Book a room at The Jefferson Hotel.

It’s called Charm City for a reason. Baltimore is bursting with personality, as proven by all the quirky attractions and events that call it home, including the annualKinetic Sculpture Race, during which huge human-powered structures lumber around the city. TheVisionary Art Museum houses an impressive collection of outsider art and the Tattoo Museum pays homage to all things ink.Savor brunch at Woodberry Kitchen and then proceed to W.C. Harlan, a moody speakeasy, for a proper co*cktail.

If you do just one thing…Explore Hampden, a uniquely Baltimore part of town that has starred in a number of John Waters' counter-culture films.

Want to stay overnight?Splurge and book a room at Sagamore Pendry Baltimore.

Road tripping onSkyline Drive is like cruising through a postcard. The picturesque byway leads you toShenandoah National Park, where you can hop on the Appalachian Trail and peep where Herbert Hoover vacationed atRapidan Camp.

If you do just one thing…Stargaze in the Big Meadows area, near Rapidan Fire Road. On nights when the sky is clear enough, you can even see the Milky Way.

Want to stay overnight? Book a room at Lewis Mountain Cabins.

When you’ve had your fill of cotton candy, explore other Ocean City boardwalk novelties like a carousel from 1912 and a miniature golf course. Of course, there’s also the beach. (You brought SPF along for the ride, right?) In terms of food, make sure to stop byFractured Prune, an outpost that only sells fried doughnuts that you can customize to your liking.

If you do just one thing… Indulge ina lovely picnic atNorthside Park, a 58-mile public recreation area.

Want to stay overnight? Book a room at Northwood Inn Bed and Breakfast.

This is an animal lover’s paradise. Let’s start with the wild ponies that reside in this popular island park. You can look at them but make sure not to touch or feed them, they’re known to be vicious and attack visitors for their food. To see dolphins, which are usually spotted, camp out on the beach. There are also deers and over 200 species of birds on the island—what else could you ever dream of?

If you do just one thing…See all the animals, obviously.

Want to stay overnight?Book a room atHotel Atlantic.

Home to the historicUniversity of Virginia, Charlottesville is at once rooted in tradition and infused with a youthful energy. Situated in the heart of Virginia wine country, the city offers a number of wineries that are worth a visit. Not into drinking? Head to theDowntown Mall, which is chock-full of restaurants, shopping and entertainment. Stop by theVirginia Discovery Museumas well, especially if you’re traveling with kids.

If you do just one thing…VisitMonticello, Thomas Jefferson’s impressive grounds, where he tinkered with famous inventions.

Want to stay overnight? Book a room at Dinsmore Boutique Inn.

You don’t need a set of sea legs to fully enjoy Annapolis. Though there are plenty of water-related activities—including chartered sailing trips, canoeing and lighthouse, tours—landlubbers can appreciate the grounds of the United States Naval Academy, which offers tours of the esteemed school. A robust restaurant scene includes Vida Taco BarandPreserve, an esteemed Annapolis newcomer focused on sustainability and fresh ingredients.

If you do just one thing…Pick up some reading material atBack Creek Books and enjoy your new purchases over a cup of joe at Ceremony Coffee Roasters. Oh, and relax.

Want to stay overnight? Book a room at The Annapolis Inn.

Bonnie Blue Bakery alone is worth the trip to this rural slice of Virginia. The rustic, from-scratch shop is known for its Texas-style BBQ and biscuits, which usually sell out before lunchtime. The charming Museum of the Shenandoah Valley will give you a deeper appreciation of the region, while Village Square Restaurant offers a number of sleek dishes and craft co*cktails.Looking to mix it up? Hopscotch Coffee & Records is a funky venue for exploring vinyl while sipping your favorite beverage.

If you do just one thing…Eat. A lot.

Want to stay overnight? Book a room at L'Auberge Provencale.