Sure, you could spend your entire Washington, D.C., visit taking in the fascinating history and culture that pervades every corner of the nation’s capital. But that would mean missing out on all the treasures a short drive away in neighboring states. Not to worry, we’ve compiled a list of road trip-worthy spots that show off the best of what this diverse region has to offer.
D.C.’s neighbor to the north—also easily reached by train—offers acclaimed waterside attractions and a unique quirky charm. Among the local obsessions? Pro sports teams (Orioles and Ravens), blue crabs with Old Bay seasoning and off-beat film director John Waters. Begin the day at Southern-style breakfast spot Miss Shirley’s Café (try the eggs Benedict with crab cakes and fried green tomatoes).
Then stroll the Inner Harbor, home to the famed National Aquarium, or board a water taxi to Fort McHenry, birthplace of the national anthem. Don’t miss the American Visionary Art Museum, a one-of-a-kind showcase for works by self-taught creatives. After all that exploring, savor more local flavor at popular eateries like Woodberry Kitchen, run by James Beard Award-winning chef Spike Gjerde. 40 miles northeast
To explore Virginia’s fabled “horse country,” set the GPS for this storybook hamlet founded in 1787. Middleburg once served as the halfway point between Alexandria and Winchester along the bustling Ashby Gap trading route (today’s Route 50), and it’s drawn celebrity residents from Jackie Kennedy to Robert Duvall.
Along the main street, find upscale boutiques and the historic Red Fox Inn & Tavern, in operation since 1728. At the posh Salamander Resort & Spa, you can saddle up for a trail ride followed by the “riders’ relief” massage or cabernet scrub. The nearby National Sporting Library & Museum features equestrian-themed artwork and literature. The area is known for its vineyards, too. Sample the sips at Boxwood Estate Winery, which produces luscious reds in the Bordeaux tradition. 45 miles west
Harpers Ferry, West Virginia
Cross the border into West Virginia to experience this historic and picturesque destination at the confluence of the Potomac and Shenandoah rivers. The Appalachian Trail runs through the heart of the tiny town, where attractions include museums, shops and Civil War battlegrounds. (In 1859, abolitionist John Brown famously led a raid on the U.S. armory here.)
Harpers Ferry National Historical Park features about 20 miles of hiking trails, ranging from easy, riverside strolls to eight-mile-long mountain ascents. In warmer months, companies like River Riders offer tubing and rafting excursions. Fuel up for big adventures at Country Café & General Store or Cannonball Deli, or reward yourself afterward at Bistro 1840. 67 miles northwest
Shenandoah National Park, Virginia
Celebrate the National Park Service in this nature lover’s oasis in the Blue Ridge Mountains. The 196,000 acres of protected wilderness offer stunning vistas and recreation options aplenty. In any season—and especially during autumn’s brilliant display of foliage “fireworks”—cruise along Skyline Drive, a National Scenic Byway that runs the length of the park. (Enter at Front Royal from I-66 west.)
The many hikes here range from easy strolls to thigh-burning climbs and include a section of the Appalachian Trail. One of the most popular (and challenging) is the route up Old Rag Mountain, which leads to beautiful payoffs at the top. Visit the trail on weekdays to encounter less foot traffic, and keep an eye out for the resident black bears, white-tailed deer and bobcats. 75 miles west
Eastern Shore, Maryland
Across the Chesapeake Bay, discover charming waterside villages like St. Michaels, which served as a trading post for tobacco farmers and trappers in the mid-1600s. Today, visitors learn about the region’s fascinating past and present at the Chesapeake Bay Maritime Museum. Walk along the enchanting streets, or explore by bike, kayak or even skipjack sailing jaunts.
Then enjoy treats at Justine’s Ice Cream Parlour or Lyon Distilling Co. Popular eateries include “dock and dine” spots like The Crab Claw and Foxy’s Harbor Grille, plus Bistro St. Michaels, Ava’s Pizzeria and Stars restaurant inside the Inn at Perry Cabin (of “Wedding Crashers” fame). 80 miles east
A longer drive but still doable in a day, Thomas Jefferson’s home has been a UNESCO World Heritage Site since 1987. On a beautiful hilltop perch near Charlottesville, history buffs take guided tours of the house that the third president called his “essay in architecture.” (Reserve tickets in advance online.) The grounds also include a restored wine cellar and orchards, in addition to vegetable and flower gardens, further evidence of Jefferson’s wide-ranging interests.
Afterward, continue the history lesson with a throwback meal at nearby Michie Tavern, or sample modern-day varietals at Blenheim Vineyards, owned by musician Dave Matthews. If you have time, wander the elegant campus of The University of Virginia, founded and designed by Jefferson. 120 miles southwest