The 7 Most Charming Weekend Getaways from DC

Ah summer, the very best of seasons. We wait all year for it, but once summer (and all of its humidity and mosquitoes) officially descends on DC, there’s nothing like getting out of town. Along with a beach day or swimming hole afternoon, a weekend escape is on our summer bucket list, and luckily, our region is filled with easy getaways, minimal driving—and no pricey plane tickets—required.

The possibilities are endless when planning a summer escape from DC, whether you’re an avid hiker or your idea of the great outdoors is lifting a glass of petit manseng in a vineyard. Here are our seven favorite getaways for a reprieve from DC this summer.

Distance from DC: 45 minutes

Annapolis is a town that lives for summer, with its deep connection to all things nautical (it’s dubbed the sailing capital of the United States and it’s also homebase for the US Naval Academy) and its narrow historic streets. At just under an hour from the district, Annapolis also makes an easy weekend destination or even day trip when you’re really craving some Old Bay with your dinner.

It's tempting to want to spend all of your time in Annapolis out on the water, and one of the best ways to explore the Chesapeake Bay—if you don’t have a sailboat or yacht, that is—is by snagging a seat on the Wilma Lee, one of the last remaining skipjacks in Annapolis (in the city’s heyday there were close to 1,000). You can join a two-hour daytime sail or opt for a sunset sail where adult beverages come with the ticket. Don’t fear if you arrive in bad weather as the city is as serious about its museums as its seafood. There’s plenty of great ones to wander through—check out The Museum of Historic Annapolis, The Banneker-Douglass Museum, and The Annapolis Maritime Museum. 

The Graduate Hotel has quirky rooms and a central location that make it a great place to lay your head after a full meal at local gems like Chick & Ruth’s, Preserve, Forward Brewing, and Leo. 

Distance from DC:1 hour and 30 minutes

Tourists and day trippers from DC make the sleepy hamlet of St. Michaels, on Maryland’s Eastern Shore, positively buzzy in the summer and for good reason: the town is loaded with charm. It doesn’t hurt that the area is also renowned for its crabs, which are in season from April to November.

You might recognize St. Michael’s from the movie Wedding Crashers which was filmed, in part, at the town’s Inn at Perry Cabin. Even if you don’t stay the night at the five-star hotel, a walk around the grounds is fun, as is booking a slot for afternoon tea.

St. Michaels is highly walkable and window shopping on the town’s main street—South Talbot Street—is a must. You’ll find lots of gift and beachy shops like The Preppy Redneck, Olde Town Candy Company, and Chesapeake Trading Company. But, this being the eastern shore, don’t stay too long in town and instead, make for the water. Sail Selina II offers daytime and sunset sails, some of which are BYOB, and others offer wine and beer tastings. Back on dry land, grab a meal at Ruse, a newer, upscale casual spot with an impressive selection of oysters or The Crab Claw, a classic, come-as-you-are spot on the water. Eastern Shore Brewing is great for a before or after meal brew.

In addition to the iconic Inn at Perry Cabin, you’ll find a lot of B&Bs in town as well as The Harbour Inn and The Wildset Hotel.

Distance from DC: 1 hour and 45 minutes

A stone’s throw from Shenandoah National Park and the Skyline Drive, Sperryville is what many hikers dream about: a small town with amazing pizza and cocktails to celebrate a long day climbing mountains. After you’ve hit the trails (we love the challenging 12.7-mile out-and-back Hazel River Trail and the 7.5-mile loop at Little Devil Stairs), head into town for some much deserved refreshment.

Although a blink-and-you-miss it town, Sperryville is something of a culinary wonderland. Stop in at theCorner Storefor fresh produce and an expertly curated wine selection, grab a cocktail (some of the best we’ve found outside DC) atBar Francis, and a fresh pie atRappahannock Pizza Kitchen. Also, make time for Pen Druid Fermentation which serves naturally made beers and ciders, andCopper Fox Distillery’s ryes and bourbons. Sperryville is also home to Three Blacksmiths, a restaurant that serves farm-to-table dishes in a candlelit space. Plan well in advance if you want a reservation–tables tend to book out months ahead of time. Spend the night at Hopkins Ordinary, an in-town b&b that also makes its own beer.

Distance from DC: 2 hours and 30 minutes

Charlottesville, the home of the University of Virginia, quiets down when the students head out for summer break. Take advantage of the empty campus and explore the grounds and buildings designed by Thomas Jefferson. Stop in at the Rotunda, the Academic Village, and the room that once was Edgar Allan Poe’s dorm. The campus is also home to The Fralin Museum of Art which has a renowned collection of Aboriginal art.

After leaving campus (this is summer, after all!) head out into the countryside which is rich in local wineries and brimming with history. Trek over to Monticello and explore Jefferson’s complex and contradictory life and legacy, and stop by Montpelier, James Madison’s former home which is now an excellent museum. Don’t miss local wineries like Pippin Hill in North Garden and King Family in Crozet, which are worth visiting for both the vintages and the views. The one-street town of Gordonsville has a collection of charming shops like Folking, offering a curated selection of vintage clothing, goods, and quilts, andJackson & Company Marketwhere you can pick up local goods, coffee, and delicious pastries.

Stay at The Oakhurst Inn which is located on UVA’s campus and has a small pool and live jazz, or for a country retreat, Crossroads Inn, is just 15 minutes from the city and right next door to Pippin Hill.

Drive time from DC: 3 hours

The last time you went to Williamsburg may have been in elementary school. If it’s been a few decades, this might be the summer you make the drive down to the colonial town which doubles as a living history museum. For convenience, base yourself at the comfortable Williamsburg Lodge, just a few minutes walk from town. Stroll from the lodge to the colonial town and spend the day stopping in as many of the recreated shops and buildings as you choose—don’t miss the chemist, the cabinet maker, and the wig shop. You might want to add in an afternoon carriage ride or post-dinner ghost tour to see another side of the town.

While eating in one of Williamsburg’s recreated colonial taverns, like the Kings Arms, is a must, there’s plenty of modern options too. Check out The Amber Ox in town or Casa Pearl, an excellent locals-favorite oyster shack a short drive away.

When you can’t walk anymore, take a short drive over to Jamestown. Grab a drink—we like B illsburg Brewery—and hop aboard an eveningsail with Jamestown Discovery Boat Tours and end your weekend (literally) sailing into the sunset.

Distance from DC: 3 hours and 15 minutes

A pair of towns that sound like brothers, Thomas and Davis make great summer destinations and an incredibly scenic road trip from DC. The two postage-stamp–sized towns are just minutes from each other and can easily be squeezed into a single weekend. Thomas is known for its honky-tonk music venue The Purple Fiddle, and you should base your trip around their schedule, whether it’s a brand-new duo or members of Americana favorites, like Old Crow Medicine Show, on the docket. Tickets range from free to $30 depending on the act. An artistic enclave in this mountainous state, Thomas punches above its weight with galleries, a vintage store, a smattering of pottery studios, and a seriously good coffee shop called TipTop. Country roads will lead you to the town of Davis and Blackwater Falls State Park. Base yourself at the recently renovated Blackwater Falls Lodge, which allows you to stay directly in the park, with rooms that offer sweeping views and the easiest access to hiking trails.

Distance from DC: 5 hours

It’s a bit of a trek to make it to Bristol, but once you’re there you’ll be glad you made the drive. The town has the unique distinction of straddling the Virginia–Tennessee state line, but that’s hardly its only claim to fame: Bristol is considered the birthplace of country music. In the early 1900s, talent scout and music producer Ralph Peer made his way to this corner of the south and begin to record music from local musicians and amateurs. He is best known for recording the Carter Family, but the full extent of his recordings is downright impressive. Dive into the history of the genre at the Birthplace of Country Music Museum, an interactive and highly engaging Smithsonian affiliate.

Continue your country music tour by taking in a show (or a few) in town at local venues like The Paramount, The Cameo Theater,orSidetracks. But to get the most authentic country music experience, drive another half an hour or so outside of Bristol until you reach theCarter Family Foldin Hiltons, Virginia. Equal parts museum, concert venue, and dancehall, the Carter Family Hold is run by the legendary country music family. Expect local country bands, audience dancing, and $1 popcorn, and they’ll teach you how to two-step if you don’t know how. Stay overnight at The Bristol Hotel, the tallest building in town. The hotel is known for its rooftop bar which offers iconic views of the town’s neon sign.

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