Middleburg
Surrounded by horse pastures and vineyards, and with a tony downtown featuring such boutiques as the aptly named home store Crème de la Crème, this Virginia enclave is a fine choice for both romantic escapes and girlfriends’ getaways. Other draws include the luxe spa at Salamander Resort and the historic Red Fox Inn & Tavern. Distance from DC: 42 miles.
Fredericksburg
This quaint Virginia downtown offers history (among the 18th-century buildings to tour are an apothecary and the home of George Washington’s mother); lots of antiquing and shopping along Caroline Street (don’t miss Riverby Books); and, befitting a college town, cheap eats including Freddy Donuts and Benny Vitali’s massive pizza slices. Don’t have a car? Take the train. Distance from DC: 52 miles.
Shepherdstown
Established in 1762, this West Virginia college town is minutes from the banks of the Potomac. Walk or bike the C&O Canal towpath or rent a kayak from Shepherdstown Pedal & Paddle. After, head to Ger-man Street, the main drag, for a burger at Mecklenburg Inn, an English pub with a beer garden. Distance from DC: 77 miles.
Chestertown
This Eastern Shore town showcases one of Maryland’s greatest concentrations of 18th-century buildings. Along the red-brick sidewalks, you’ll come across the studios of artists drawn to live here. A self-guided walking tour is at kentcountyhistory.org. Distance from DC: 80 miles.
St. Michaels
This Eastern Shore town is popular for a reason—and there’s a lot to do outside for those hesitant to hang indoors. Restaurants such as the Crab Claw and Foxy’s Harbor Grille offer alfresco waterfront dining, and there are plenty of patios in town. (We like dog-friendly Ava’s Pizzeria.) You can rent a bike or kayak at Shore Pedal & Paddle. Or head to the Chesapeake Bay Maritime Museum, which offers outdoor exhibits and scenic river cruises. Distance from DC: 82 miles.
Lewes
This picturesque Delaware town is a stone’s throw from the beach-es of Cape Henlopen State Park. Even if you don’t hit the sand, you can bike the pleasant Junction & Breakwater Trail to Rehoboth, looping back through the marshes of Gordons Pond Trail, then refuel at popular Agave Mexican Restaurant. Distance from DC: 119 miles.
Staunton
This Shenandoah Valley charmer is far for a day trip but worth a several-day stay: Besides historic architecture and one of the “greatest main streets in America” according to Travel & Leisure,it’s got live Shakespeare at Blackfriars Playhouse; the Woodrow Wilson Presidential Library and other museums; and buzzy restaurants such as the Shack and Zynodoa. Distance from DC: 156 miles.
Lexington
This mountain town is a good base for outdoor fun: kayaking and hiking, a drive on the Blue Ridge Parkway, a movie at Hull’s Drive-In, an open-air concert at Lime Kiln Theater, and a visit to Natural Bridge, a 215-foot-tall limestone marvel. Cap off a day with a beer at Devil’s Backbone’s Tap Room, dinner at the Red Hen (yes, that Red Hen), and a stay at the Georges. Distance from DC: 189 miles.
Enjoy a relaxing river cruise in St. Michaels.
Photograph courtesy of Chesapeake Bay Maritime Museum
This article appears in the May 2021 issue.
Sherri Dalphonse joined Washingtonian in 1986 as an editorial intern, and worked her way to the top of the masthead when she was named editor-in-chief in 2022. She oversees the magazine’s editorial staff, and guides the magazine’s stories and direction. She lives in DC.
