If you live in Arlington, VA, you’re perfectly positioned for unforgettable weekend getaways. Whether you crave the energy of a bustling city, the serenity of the mountains, or the charm of small-town America, there’s an ideal destination within a few hours’ drive. From historic sites and scenic vineyards to coastal escapes and cozy retreats, here are some of the best weekend trips from Arlington to help you recharge, explore, and fall in love with the region all over again.
1. Charlottesville, VA – History, Wine, and the Blue Ridge
Distance: ~2.5 hours southwest
Charlottesville is a quintessential Virginia escape that perfectly blends history, culture, and relaxation. Begin your weekend by exploring Monticello, the estate of Thomas Jefferson, where you can tour the grounds and take in sweeping views of the Blue Ridge Mountains. Downtown Charlottesville offers charming boutiques, galleries, and an array of local restaurants—don’t miss the lively Downtown Mall, one of the longest pedestrian malls in the country.
Wine lovers will want to dedicate an afternoon to exploring the Monticello Wine Trail, featuring more than 30 wineries nestled among rolling hills. End your evening with a farm-to-table dinner at The Local or a casual bite at Three Notch’d Brewing Company.
Perfect for: History buffs, wine enthusiasts, and couples looking for a romantic escape.
2. Shenandoah National Park – Nature and Tranquility
Distance: ~2 hours west
For those craving peace, fresh air, and mountain views, Shenandoah National Park is the perfect weekend destination. Drive along Skyline Drive, where every twist and turn reveals panoramic overlooks, waterfalls, and endless trails. Hike to Old Rag Mountain or Dark Hollow Falls for a dose of adventure, or take an easier stroll along the Stony Man Trail for breathtaking views with less exertion.
Book a stay at one of the park’s cozy lodges, such as Skyland or Big Meadows, or opt for a nearby cabin or bed and breakfast in Luray or Front Royal. Don’t forget your camera—sunsets from the overlooks are absolutely spectacular.
Perfect for: Outdoor enthusiasts and anyone needing a digital detox.
3. Annapolis, MD – Nautical Charm by the Bay
Distance: ~1 hour northeast
Just a short drive from Arlington, Annapolis delivers waterfront relaxation and rich maritime history. Stroll through the cobblestone streets of the Historic District, lined with 18th-century homes, or tour the U.S. Naval Academy to glimpse the traditions of America’s sailors.
Take a boat cruise on the Chesapeake Bay or rent a kayak to explore the peaceful coves. Fresh seafood is the star of the show here—head to Cantler’s Riverside Inn for authentic Maryland blue crabs or Osteria 177 for upscale Italian dining with a coastal twist.
In the evening, relax with a cocktail by the water as sailboats glide by, and you’ll see why Annapolis is one of the region’s most beloved escapes.
Perfect for: Foodies, boat lovers, and families.
4. Harpers Ferry, WV – History and Adventure Meet
Distance: ~1.5 hours northwest
Perched at the confluence of the Potomac and Shenandoah Rivers, Harpers Ferry is where history and outdoor adventure meet. This picturesque town played a pivotal role in the Civil War and offers a mix of historic sites and stunning natural scenery.
Spend your morning exploring the Harpers Ferry National Historical Park, then cross the footbridge to the Appalachian Trail Conservancy headquarters for an iconic photo. For thrill-seekers, the nearby rivers offer some of the best whitewater rafting and tubing in the region.
Cap off your trip with a visit to Almost Heaven Pub and Grill, where you can enjoy local brews and scenic views of the surrounding mountains.
Perfect for: History lovers and outdoor adventurers.
5. Richmond, VA – Art, Food, and Riverfront Fun
Distance: ~2 hours south
Richmond is a vibrant city with a creative pulse and deep Southern roots. Stroll along Monument Avenue to admire its historic architecture, then explore the Virginia Museum of Fine Arts, one of the best in the Southeast.
Food lovers will be in heaven—Richmond’s culinary scene is thriving, with hot spots like L’Opossum, Shagbark, and ZZQ drawing national attention. For a more relaxed vibe, head to the Scott’s Addition neighborhood, where craft breweries, cideries, and rooftop bars create a perfect weekend buzz.
If the weather’s nice, spend time along the James River, where locals kayak, sunbathe, and hike the trails that run right through the city. Richmond perfectly combines culture, cuisine, and outdoor adventure.
Perfect for: Art aficionados, foodies, and urban explorers.
6. The Eastern Shore – Coastal Calm and Chesapeake Beauty
Distance: ~3 hours east
If you’re in the mood for a coastal escape, Virginia’s Eastern Shore offers tranquil beaches, small-town charm, and some of the best seafood around. Cross the stunning Chesapeake Bay Bridge-Tunnel, and you’ll feel a world away from the city bustle.
Stop in Cape Charles, a picturesque town with boutique shops, cozy cafés, and a calm beach perfect for families. Enjoy oysters at The Oyster Farm Seafood Eatery or sunset drinks at The Shanty. For a nature-focused trip, visit Chincoteague Island and Assateague National Seashore, where wild ponies roam the dunes and migratory birds fill the skies.
Perfect for: Beach lovers and anyone seeking a peaceful retreat.
7. Gettysburg, PA – Step Back in Time
Distance: ~2 hours north
Steeped in Civil War history, Gettysburg is both solemn and inspiring. Explore the Gettysburg National Military Park, where expert guides bring the epic three-day battle to life. The park’s museum and cyclorama offer fascinating context, while the battlefield itself is hauntingly beautiful.
Beyond history, Gettysburg’s modern side surprises visitors with charming wineries, antique shops, and quaint inns. Dine at Dobbin House Tavern, a historic restaurant dating back to 1776, and spend the night at a cozy bed and breakfast.
Perfect for: History enthusiasts and couples who love heritage-rich getaways.
8. Baltimore, MD – Harbor Views and Urban Energy
Distance: ~1 hour northeast
Baltimore offers a perfect blend of culture, sports, and seaside energy. Spend your weekend exploring the Inner Harbor, where you’ll find the National Aquarium, historic ships, and waterfront restaurants. The Fells Point neighborhood offers cobblestone streets, pubs, and live music, while Federal Hill delivers sweeping views of the skyline.
Don’t miss the Baltimore Museum of Art or an Orioles game if you visit during baseball season. Grab dinner at Thames Street Oyster House or Woodberry Kitchen to experience the city’s famous Chesapeake-inspired cuisine.
Perfect for: City explorers and families seeking a fun, easy trip.
Plan Your Next Adventure from Arlington
Living in Arlington means you’re surrounded by some of the East Coast’s most dynamic destinations. Whether you prefer a quiet mountain lodge, a vibrant cityscape, or a seaside escape, all these getaways are just a short drive away. With so many options, your only challenge will be deciding where to go first!
Discover More with The Tom Buerger Team
If you love Arlington’s unbeatable location and community, why not make the area your home base for a lifetime of weekend adventures? The Tom Buerger Team of Compass are Washington, DC real estate experts who specialize in helping buyers and sellers navigate the market with confidence, insight, and integrity. Whether you’re looking to upgrade, downsize, or invest in a property near the city’s best escapes, their local expertise will guide you every step of the way.
Start your next chapter today—visit
buyandselldc.com to connect with The Tom Buerger Team.
