Best Day Trips from Washington, DC for a Fall Escape
There’s much to love about fall in Washington, D.C. Golden hour seems to stretch, the leaves begin to change, and somehow the District is even more photogenic. In a city as fast-paced as D.C., nature’s annual shift can be read as a gentle reminder to slow down and reconnect with the great outdoors before we head back in for winter.
The best day trips from Washington, D.C. for a fall escape do just that. From leaf-peeping road trips to winery tours to wild underground caves, here are the top four day trips from D.C. to book this season.
1. Loudon County, VA
Distance from DC: 25 miles / 60 min.
Visit for: wineries, gastronomy, scenic road trips
Known as D.C.’s wine country, this North Virginia destination makes a perfect D.C. day trip for foodies and wine aficionados. Loudoun County has more than 50 wineries and tasting rooms that range in price and style, from historic barrel rooms to glamorous halls with views of the Blue Ridge Mountains. Many welcome families, too, with acres of farmland to run around.
Fall is a great time of year to visit Loudon, when all those rolling hills and beautiful vistas are bursting with autumn colors. Start your journey at Stone Tower, a family-owned winery and 300-acre estate that blends old and new world style. Guided cellar tours and dog-friendly spaces make it a popular go-to for families and groups. Continue to Fabbioli Cellars for a sip of award-winning cabernet franc, or visit Sunset Hills, an eco-conscious, solar-powered vineyard housed in a historic Amish barn. If you’ve had enough wine, Mt. Defiance is a fun local cidery with live music and seasonal events.
Beyond the glass, Loudoun County offers plenty to explore. Lean into fall at Great Country Farms with apple cider donuts, corn mazes, and a pumpkin patch. Check out Hammerdown BBQ on Route 50 for St. Louis-style ribs and cozy farmhouse atmosphere. Go for garlic naan and tandoori cooking at Loudoun’s popular Indian restaurant, Biryani Grill, or learn about America’s equestrian history at The National Sporting Library & Museum, hailed by Conde Nast Traveler as one of the 50 best museums in the U.S.
2. Frederick, MD
Distance from DC: 1 hour, 10 min.
Visit for: art & culture, shopping, outdoor recreation
Small town charm meets world-class art and culture in Frederick, Maryland. This picturesque county is an ideal DC day trip for those who like to gallery hop, boutique shop, and squeeze in outdoor recreation all in the same day.
Visit downtown for 18th century architecture and hundreds of boutique shops. See what’s on at Weinberg Center, a historic theater showing films, Broadway musicals, author events and more. Head to New Spire Arts for up-and-coming productions in a black box theater, or walk the idyllic Carroll Creek path for live music and fall foliage.
Speaking of foliage, Frederick has more than 90 park facilities made for outdoor fun: hiking, horseback riding, mountain biking, and lots more. Catoctin Mountain Park is a must for trout fishing in the fall, and a worthwhile stop for history buffs; Camp David is located at the mountaintop. Visit Maryland’s highest cascading waterfall at Cunningham Falls State Park or wander the storied C&O Canal along the Potomac River.
3. Annapolis, MD
Distance from DC: 50 min.
Visit for: romance, waterfront dining, history
It’s all about the harbor in Annapolis, Maryland. Sailing, seafood, and maritime history go way back in this gorgeous state capital, located less than an hour’s drive from Washington, D.C.
Annapolis is ideal for a girls’ getaway or a romantic weekend, charmed with colonial architecture and waterfront restaurants that always have a local catch on the menu. Experience the culture with a sunset cruise, or visit The U.S. Naval Academy Museum for a fascinating look at seafaring.
If you’re traveling in October, don’t miss the Great Annapolis Pumpkin Carving. All month long, giant 1,000-pound pumpkins will be on display throughout town. Then, just before Halloween, a pumpkin carving contest transforms the gorges into magnificent works of art.
Shenandoah Valley, VA
Distance from DC: 1 hour, 30 min.
Visit for: outdoor adventure, hiking, scenery
Shenandoah Valley is just an hour and a half west of Washington, D.C. But once you arrive, you’ll feel like you’re in a whole new world.
Underground caves. Towering mountains. Gold and crimson leaves. Shenandoah is a nature lover’s dream and just as suited for those who like adventure. Start at Shenandoah National Park and pick your thrill: miles of hiking trails, horseback rides, a leaf-peeping road trip on Skyline Drive, or maybe a night of stargazing. Close to the park, don’t miss a guided tour through Luray Caverns, a sprawling network of underground caves that look straight out of a cinema.
This part of Virginia is also acclaimed for a small-but-mighty scene of local winemakers. Get a taste at award-winning vineyards like Cave Ridge and Wolf Gap, both with stunning vistas that stretch for miles.
Where to Stay: The Morrow Hotel
Come back from the day’s adventure and relax at The Morrow Hotel. Our Washington D.C. suites are designed for just that, with self-care packages and wellness programs to keep you feeling your best.
Plus, as one of the top hotels in northeast DC, The Morrow offers world-class dining at Marcus DC, recently named one of the 25 best hotel restaurants in the world by Travel + Leisure magazine.
Explore seasonal offers at The Morrow and join us for a D.C. fall getaway.