Travel

Small-Town Getaways in Driving Distance of Washington, DC

Amble, window-shop, dine—as a day trip or overnight

Enjoy a relaxing river cruise in St. Michaels. Photograph courtesy of Chesapeake Bay Maritime Museum.

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. 

More:
Executive Editor

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.