Washington, D.C., is surrounded by diverse destinations perfect for a weekend retreat. From historic towns to scenic mountain escapes, these locations offer something for every traveler. Below, we explore the best weekend getaways within a short drive of the nation’s capital.
1. Annapolis, Maryland: A Historic Maritime Retreat
Chesapeake Bay Views and Sailing Adventures
Annapolis, the capital of Maryland, is a waterfront city known for its colonial history and maritime culture. The city’s location along the Chesapeake Bay makes it a prime destination for sailing, fishing, and waterfront dining.
Must-Visit Attractions
- U.S. Naval Academy: Take a guided tour of this prestigious institution.
- Historic Downtown: Walk along cobblestone streets lined with 18th-century buildings.
- Chesapeake Bay Sailing Tours: Experience a sunset cruise on the bay.
- Maryland State House: Explore the oldest state capitol still in use.
Local Cuisine
- Enjoy fresh seafood at Cantler’s Riverside Inn or try Maryland’s famous crab cakes at O’Learys Seafood Restaurant.
2. Charlottesville, Virginia: Wine Country and Presidential History
Monticello and Vineyard Tours
Charlottesville is home to Monticello, Thomas Jefferson’s estate, along with numerous wineries in the surrounding countryside. The rolling hills of the Blue Ridge Mountains create a picturesque backdrop.
Must-Visit Attractions
- Monticello: Tour Jefferson’s historic home and gardens.
- University of Virginia: Visit the Rotunda, designed by Jefferson himself.
- Carter Mountain Orchard: Pick seasonal fruits with panoramic views.
- Barboursville Vineyards: Sample award-winning Virginia wines.
Local Cuisine
- The Alley Light serves French-inspired small plates.
- Mas Tapas offers an extensive selection of Spanish tapas.
3. Shenandoah National Park, Virginia: A Scenic Outdoor Escape
Skyline Drive and Hiking Trails
Shenandoah National Park offers breathtaking views, waterfalls, and outdoor recreation. Located along the Blue Ridge Mountains, it is an ideal retreat for hiking enthusiasts and nature lovers.
Must-Visit Attractions
- Skyline Drive: A 105-mile scenic road with overlooks.
- Old Rag Mountain: A challenging but rewarding hike.
- Dark Hollow Falls: A short hike to a picturesque waterfall.
- Luray Caverns: Explore one of the largest cave systems in the U.S.
Local Cuisine
- Skyland Resort offers Appalachian-inspired dishes with mountain views.
- Gathering Grounds Patisserie & Café in Luray is known for fresh-baked pastries.
4. Harpers Ferry, West Virginia: History and Outdoor Activities
Civil War History and River Adventures
Harpers Ferry is a small town at the confluence of the Potomac and Shenandoah Rivers, known for its historical significance and outdoor activities.
Must-Visit Attractions
- Harpers Ferry National Historical Park: Walk through 19th-century buildings and museums.
- Appalachian Trail Conservancy: Start a hike along this famous trail.
- River Tubing and Kayaking: Paddle through the scenic waterways.
- Jefferson Rock: A viewpoint with a sweeping landscape.
Local Cuisine
- The Anvil Restaurant serves hearty American fare.
- Hannah’s Train Depot is a casual eatery with comfort food classics.
5. Richmond, Virginia: Arts, Culture, and History
Museums and James River Adventures
Richmond blends historic charm with modern attractions, making it a well-rounded weekend destination.
Must-Visit Attractions
- Virginia Museum of Fine Arts: A diverse collection of art from around the world.
- Hollywood Cemetery: A historic resting place for notable figures.
- James River Park System: Kayaking, paddleboarding, and scenic trails.
- Carytown: A vibrant shopping and dining district.
Local Cuisine
- L’Opossum serves French-inspired dishes with a creative twist.
- The Roosevelt specializes in Southern cuisine.
6. St. Michaels, Maryland: A Quiet Eastern Shore Retreat
Chesapeake Bay Maritime Heritage
St. Michaels offers a peaceful getaway along Maryland’s Eastern Shore, where visitors can experience a mix of history and waterfront relaxation.
Must-Visit Attractions
- Chesapeake Bay Maritime Museum: Learn about the region’s seafaring history.
- Lighthouse Tours: Visit Hooper Strait Lighthouse.
- Sailboat Charters: Enjoy a private sailing excursion.
- Tilghman Island: A short drive for a secluded coastal experience.
Local Cuisine
- The Crab Claw serves traditional Maryland crab dishes.
- Ava’s Pizzeria & Wine Bar is a favorite for gourmet pizza.
7. Gettysburg, Pennsylvania: A Journey Through American History
Battlefield Tours and Historic Town Exploration
Gettysburg is an essential stop for history buffs, offering in-depth insights into the Civil War’s most significant battle.
Must-Visit Attractions
- Gettysburg National Military Park: Take a guided battlefield tour.
- Eisenhower National Historic Site: Visit the home of the former president.
- Jennie Wade House: Learn about the only civilian casualty of the battle.
- Downtown Gettysburg: Walk through shops, galleries, and historic sites.
Local Cuisine
- Dobbin House Tavern offers colonial-era dining.
- Blue & Gray Bar & Grill features themed burgers named after generals.
8. The Greenbrier, West Virginia: A Luxury Mountain Retreat
Resort Amenities and Natural Beauty
The Greenbrier is a historic luxury resort in the Allegheny Mountains, offering top-tier accommodations and outdoor activities.
Must-Visit Attractions
- The Greenbrier Bunker: A Cold War-era government facility.
- Casino Club: A high-end gaming experience.
- Golf Courses: Championship-level courses with scenic views.
- White Sulphur Springs: Known for its natural mineral springs.
Local Cuisine
- Main Dining Room offers fine dining with seasonal menus.
- Draper’s Café serves casual Southern dishes.
9. Deep Creek Lake, Maryland: A Four-Season Outdoor Playground
Lake Activities and Mountain Adventures
Deep Creek Lake is a versatile destination with summer water sports and winter skiing.
Must-Visit Attractions
- Deep Creek Lake State Park: Boating, fishing, and hiking.
- Wisp Resort: A hub for skiing and snowboarding.
- Swallow Falls State Park: A scenic waterfall hike.
- Adventure Sports Center International: Whitewater rafting on a man-made course.
Local Cuisine
- MoonShadow offers farm-to-table dining.
- Dutch’s at Silver Tree is known for its lakeside seafood dishes.
10. Rehoboth Beach, Delaware: A Classic Seaside Escape
Boardwalk Fun and Oceanfront Relaxation
Rehoboth Beach is a popular coastal town known for its boardwalk, sandy shores, and family-friendly attractions.
Must-Visit Attractions
- Rehoboth Beach Boardwalk: Lined with shops, restaurants, and amusements.
- Cape Henlopen State Park: A natural area with trails and dunes.
- Funland: Classic seaside amusement rides.
- Tanger Outlets: Tax-free shopping on name-brand goods.
Local Cuisine
- Dogfish Head Brewings & Eats offers craft beer and pub fare.
- The Blue Hen serves elevated comfort food.
Conclusion: Plan Your Ideal Weekend Escape
Washington, D.C., is within reach of countless destinations that cater to history lovers, outdoor adventurers, and those seeking relaxation. Whether exploring the historic streets of Annapolis, hiking through Shenandoah, or unwinding in Rehoboth Beach, each getaway offers a distinct experience. For more expert travel guides and automotive insights, visit CarValor.
