Fall looks even better when you’re exploring it together. Just outside Washington, DC, Montgomery County offers couples an easy escape filled with scenic mountain hikes, countryside wineries, creative date nights, and unexpected adventures. Whether you’re planning a romantic weekend or simply looking for something new to experience together, here’s how to make the most of fall in Montgomery County.

Scenic Escapes

Start your getaway with a stroll around Seneca Creek State Park, where the 3.7-mile loop winds through woods and open fields along the water. Keep an eye out for herons, turtles, and migrating birds as bald eagles soar overhead. Grab lunch or snacks and settle in with a picnic, finding the ideal spot among the wooded picnic areas overlooking the park. After your walk, head to nearby Windridge Vineyards for a dual wine tasting featuring sparkling Albariño, then settle onto the patio for live music and time around the fire pit.

For a more adventurous day outdoors, explore the C&O Canal by bike or on foot. Ride along the mostly flat, scenic towpath; take in the scenery at Great Falls; or challenge each other on the rocky terrain of the Billy Goat Trail. Then settle in for dinner at Old Angler’s Inn, just steps from the canal. Share the rack of lamb, a longtime favorite, in one of its cozy dining spaces and outdoor patios.

Extend your canal adventure with an overnight stay in a historic lockhouse, where period furnishings, books, newspapers, and vintage games offer a glimpse into life along the C&O Canal. Wake up by the water and start the morning with a bike ride together along the towpath.

Countryside Adventures

Start the day with a hike to the peak of Sugarloaf Mountain, then slow things down together over a glass of rose’ at Sugarloaf Mountain Vineyard, and live music on the patio.  Bring along a picnic or light bites and linger over views of the surrounding countryside before continuing to nearby Comus Inn for a shareable backyard cheeseboard with Jalapeno Peach chicken skewers overlooking Sugarloaf Mountain. After lunch, stop in at Homestead Farm to pick a pumpkin together, wander the working farm, and browse the market for local honey and preserves to take home.

For another countryside date, follow the Tastemakers Trail to The Crossvines in Poolesville. Settle in at the Farmhouse Bistro for a farmers market salad, shared Charcuterie Board, and a glass of wine all while taking in the natural scenery of the rural landscape. Then continue to nearby Song Dog Distillery to sample locally made Rye and Whiskey, and watch the distilling process through the tasting glass wall. End the afternoon on an open-air porch with a cocktail, live music, and scenic views of the countryside.

Creative Dates

Turn a fall afternoon into a creative date at Glen Echo Park, a former amusement park turned into a modern visual and performance arts space that also serves as a National Park. Take a ceramics, painting, or glassblowing class led by resident artists. Then trade the studio for the dance floor and learn a few salsa steps in the historic Spanish ballroom. After making something together, stroll through the park’s historic grounds and admire its Art Deco architecture before unwinding together at the nearby Irish Inn at Glen Echo during happy hour, sharing hummus and cheese flatbread in its cozy setting.

Spend a fall afternoon immersed in art at Glenstone Museum, a space that seamlessly integrates contemporary art, architecture, and nature. Wander past outdoor sculptures like Split-Rocker, and explore the galleries at your own pace. It’s the kind of afternoon that invites you to reset, reflect, and experience something beautiful together. Don’t miss Nick Cave’s Louder Still, a larger-than-life installation featuring eleven elaborately adorned figures covered in iridescent buttons and connected by a sweeping textile. After exploring Glenstone, continue the evening at Clyde’s Tower Oaks Lodge, and enjoy Faroe Island salmon surrounded by rustic fireplaces and wood-beamed ceilings.

History & Heritage

Step back in time at Josiah Henson Museum & Park and explore the life and legacy of the famed abolitionist and inspiration behind Uncle Tom’s Cabin. Tour the historic Riley-Bolton House and 1850 log kitchen, hear audio accounts from those who lived and worked on the property, and uncover remnants of the past on an archaeological tour.

Continue exploring at nearby Woodlawn Cultural Park, for a guided hike along the Underground Railroad Trail, where stories of freedom seekers and the residents who aided them are brought to life. Looking for something more active? Head to The Adventure Park at Sandy Spring and challenge each other to an aerial ropes course. Test your balance, race along zip lines, and take aim at the axe-throwing lanes while cheering each other on through the park.

Take an unexpected date aboard a historic trolley at the National Capital Trolley Museum. Ride through the woods, then explore Streetcar Hall for an up-close look at historic streetcars, including some more than a century old, offering a glimpse into how people once traveled throughout the Washington Region.

Ready to keep exploring? Taste your way through fall and savor Montgomery County’s best dishes, discover Oktoberfest celebrations around the county, or browse the Upcoming Events Calendar to find even more ways to plan your fall getaway.