Quick Getaways from D.C.: Seven Ideas for Long Weekend Road Trips
If you’re seeking a long weekend on the East Coast, but want to avoid the crush and chaos of NYC, you need to explore the D.C. area. Despite the stereotypes, there’s so much more to this part of the United States than the National Mall– it’s a centerpoint of U.S. history, culture, and natural beauty.
If you’re local to D.C., feel free to use this guide as a starting point for planning easily accessible long weekend getaways. And if you’re not already local to D.C., we have you covered. Our Washington, D.C. 100 Collection™ partner is Home Sweet City, which offers a range of curated city dwellings (from cozy apartments to luxe mansions). Home Sweet City’s beautiful rentals are thoughtfully located in desirable D.C. neighborhoods so you can stay close to significant landmarks and great food while still enjoying the privacy of a residential area.
So once you’re done touring the monuments, keep exploring– there’s plenty to enjoy within a 5 hour drive of D.C.
We’re shining the spotlight on five curated, 100 Collection™-approved locations you won’t want to miss. Book one, or plan to hit all of them to really immerse yourself in this underrated area of the United States.
1. Charlottesville, Virginia
Distance from Washington, D.C.: Approximately 2.5 hours
Charlottesville, Virginia, is a small city tucked away in the foothills of the Blue Ridge Mountains. Praised for its wineries, historic sites, and arts scene, there’s no shortage of things to do.
History buffs will love touring Monticello, the former estate of Thomas Jefferson, plus significant sites like Edgar Allen Poe’s room at the University of Virginia and the Albemarle County Courthouse (first established in 1762).
Plus, music and culture lovers can snag tickets for both big-name bands and grassroots local artists, along with dance shows and fine art exhibitions.
Stay Charlottesville, our 100 Collection partner in the area, offers an eclectic mix of chic condos, spacious estates, and beautiful antique houses that capture the historic feel of the area.
2. Shenandoah Valley & Massanutten, VA
Distance From Washington, D.C.: Approximately 2.5 hours
Calling all outdoor enthusiasts! Massanutten sits just minutes from the Shenandoah Valley, offering stunning views of rolling mountains. The area is anchored by the popular Massanutten Resort, where visitors can find activities for every season. From skiing and snowboarding to swimming at their WaterPark and golfing on scenic courses, you’ll have plenty of activities to choose from.
If you’re looking for some quality hiking, Shenandoah National Park calls with breathtaking views. Here you'll find powerful waterfalls, colorful wildflower fields, and miles of hiking trails. Whether you're hiking through forests, biking along mountain paths, or casting a line in a stream, keep your eyes peeled for wildlife that calls this park home.
Book your mountain getaway with The 100 Collection's partner, Vacation Properties Made Simple. Their collection of gorgeous cabins and lodge-style homes provides the perfect setting to unplug and immerse yourself in Virginia’s beauty.
3. Ocean City, Maryland
Distance from Washington, D.C.: Approximately 3 hours
Head to Ocean City, Maryland, to eat your fill of seafood and unwind on the beach. Ocean City has a nostalgic East-Coast feel to it due to its iconic boardwalk and old-school amusements. Snag an ice cream, wander into taffy shops, watch street performers, or hop on the Ferris wheel– whether you’re 9 or 99, there’s something for kids of all ages.
Ocean City is known for its fresh crab cakes, and you can indulge at both casual and upscale spots (but don’t worry– there are also plenty of options for family members or friends who don’t eat seafood).
When you’re planning your Ocean City trip, you’ll find beautiful options for every group size with our 100 Collection partner, Seaside Vacations & Sales. They offer well-lit, cozy houses, townhouses, and condos right on the water.
4. Chincoteague, Virginia
Distance from Washington, D.C.: Approximately 3.5 hours
Let the wild horses of Chincoteague, Virginia, drag you away. Seriously!
Chincoteague is famous for its herds of wild ponies. So if you (or your little ones) love pony-related shenanigans, make sure to book your trip for late July: you won’t want to miss the annual Pony Roundup, Swim, and Auction.
Chincoteague’s culinary scene offers fresh seafood and other local East-Coast eats ranging from savory sandwiches to sweet baked goods.
Seaside Vacations & Sales is also The 100 Collection’s partner for Chincoteague (as well as Ocean City). Each airy island villa or house has its own fresh, comfy, and slightly nautical feel.
5. Pocono Mountains, Pennsylvania
Distance from Washington, D.C.: Approximately 4.5 hours
The Pocono Mountains are an ideal fit for outdoor sportspeople. When it’s warm, enjoy rafting, kayaking, swimming, and boating. During the winter months, get ready for skiing, snowboarding, or snow tubing (followed up with some hot cocoa, of course!).
If you want a rugged-yet-sophisticated experience, you’ll love the Poconos– in addition to outdoor sports and activities, you can enjoy intentional, well-crafted seasonal cuisine and local boutiques.
Pocono Mountain Rentals, our 100 Collection partner, provides large mountain houses that combine cabin-like coziness with seriously upscale amenities (like luxe stainless steel kitchens with ample countertop space, hot tubs, and fireplaces).
6. Harpers Ferry, West Virginia
Harpers Ferry sits at the intersection of the Potomac and Shenandoah rivers, making it a prime spot for both history enthusiasts and outdoor adventurers. This small West Virginia town is home to Civil War sites, miles of hiking trails, and water activities all within walking distance.
Spend your mornings exploring the historic Lower Town's museums and shops, take an afternoon kayaking trip down the Potomac, or hike a portion of the Appalachian Trail that runs right through town. The area offers excellent rock climbing spots and mountain biking trails for those seeking more exhilarating activities.
Mountain Mama, our 100 Collection partner in Harpers Ferry, began when owners Eddie and Mary discovered their own perfect escape here. Their properties feature scenic valley views, outdoor firepits, and screened porches that let you soak in the surroundings. Mountain Mama’s vacation rentals will give you a reason to return to Harpers Ferry for years down the road!
Ready to start planning?
As you map out your D.C. area itinerary, we encourage you to plan your destinations thoughtfully so you can make the most out of your trip.
If you’re already a D.C. resident or you live close by, consider carving out a long weekend for yourself and your loved ones sometime soon.
Or, if you’re farther away, we suggest planning a few days at each location– there aren’t many other places where you’re a stone’s throw away from the forest, the beach, and tons of historic landmarks.
Curious about the other curated destinations in The 100 Collection™?
