The summer road trips are behind us, the kids are back in school, and the crisp, cool air of fall is rolling into Mountain Maryland. While we often dream about far-off adventures, this season invites us to rediscover the treasures tucked right here at home in Allegany County, Maryland—perfect for anyone searching for things to do in Cumberland MD or planning a fall weekend getaway. From historic sites to cozy coffee shops, fall festivals to scenic rail rides, there’s no better time to explore your backyard with fresh eyes.
Whether you’re craving a little history, outdoor beauty, or simply some hometown fun, here’s your two-day itinerary for being a tourist in your own hometown.
Day One: Cumberland Charm
Morning: Coffee + Culture
Ease into your weekend with a cup of craft-roasted coffee at Basecamp Coffee Company or Corner Tavern and Cafe, both known for their community vibe and quality brews. Then head downtown to the Allegany Museum, where history comes alive through exhibits spanning 12,000 years—from the region’s first Native American residents to the booming days of industry and transportation. With over 50,000 artifacts on display, the museum tells the story of how the National Road, B&O Railroad, and C&O Canal transformed Cumberland into a hub of innovation and growth, making it one of the top historic attractions in Western Maryland. Admission is free, making this the perfect place to spark your hometown pride.
Midday: Stroll + Shop the New Downtown City Center
The newly revitalized Baltimore Street in Downtown Cumberland is brimming with fresh energy—boutiques, eateries, public art, and seasonal events. Wander the pedestrian-friendly brick streets, browse local shops, and grab a bite at one of the many restaurants serving everything from casual comfort food to creative Appalachian cuisine.
Afternoon Adventure: Ride the Rails
Nothing says “Mountain Maryland” like a trip on the Western Maryland Scenic Railroad. This fall, go beyond the classic Frostburg Flyer excursion and book a ticket for the Sunset on the Mountain train. Departing at 7:00 PM, this experience blends acoustic music, hors d'oeuvres, and sweeping mountain views as you climb from Cumberland to Frostburg in lounge, dome, or open-air seating. Sip a craft cocktail as the sun dips below the ridges. There’s truly nothing like it.
Not in the mood for a train ride? Try a puzzle-solving adventure at Exit Strategy Escape Room in Cumberland, where you and your friends can race the clock in themed challenges that put your teamwork and wits to the test.
Evening: Live Music Meets Fine Art
Cap off your night at Gallery Stage, an intimate listening room tucked inside the Ferleman Gallery. This bespoke venue marries art and acoustics, creating a one-of-a-kind backdrop for live performances. With curated craft cocktails and mocktails to match the vibe, it’s the perfect way to wind down your first day as a “tourist” in your hometown.
Looking for something more high-energy? Head to Fore Axes in Downtown Cumberland, where you can try axe throwing, virtual golf, and other interactive games as a perfect way to end your weekend with friends.
Day Two: Frostburg Fun & Fresh Air
Morning: Tracks & Yaks Adventure
Fuel your morning in Frostburg with a handcrafted latte from Clatter Café or a cozy breakfast at Mountain City Coffeehouse & Creamery, both local favorites. Then head to the historic Frostburg Depot for an outdoor adventure with Tracks and Yaks. Choose from:
- Woodcock Hollow Express (weekends through November): A 7-mile railbike ride starting at the historic Frostburg Depot, ending with a shuttle return.
- Mountainview Fireside Social (beginning late September): Pedal at dusk, coast down the tracks as the mountains glow with fall color, then gather around a campfire for s’mores and storytelling.
Prefer traditional cycling? Rent a bike and ride the Great Allegheny Passage or the C&O Canal Towpath, with shuttle options available to make planning easy.
Midday: Frostburg Eats & Downtown Wander
Fuel up with lunch at a Frostburg favorite like the Princess Restaurant, a downtown institution that’s been serving hearty meals for over 75 years. Be sure to check out the famous Truman Booth, where President Harry Truman once dined in the 1950s. Or, if you’re craving pub fare, stop by Sand Springs Saloon for burgers, wings, and comfort food classics.
After lunch, stroll Frostburg’s historic Main Street, explore quirky shops and galleries, or step back in time at the Thrasher Carriage Museum or the Frostburg Museum.
Afternoon: Festivals & Celebrations
Fall in Allegany County is festival season, with some of the best fall festivals in Western Maryland. Depending on the weekend, you could find yourself at:
- Heritage Days & Whiskey Rebellion (Sept. 11–14): Cumberland’s signature history and heritage festival, featuring reenactments, artisans, railroading traditions, antique cars, food, music, and family fun. This year also brings the return of Maryland Railfest 2025, with steam locomotive No. 1309 and the BBQ Choo Choo feast train.
- Appalachian Festival at Frostburg State (Sept. 18–20): Celebrating 20 years of Appalachian culture with traditional music, dance, storytelling, artisans, and a capstone concert featuring Tim O’Brien and Jan Fabricus.
Evening: Cheers to Local Flavor
Close out your weekend with a toast at 1812 Brewery or Locust Post Brewery.
At 1812, enjoy a beautiful patio and loafing barn along with rotating live music and food vendors each weekend. Locust Post, set on a 26-acre farmstead, blends art, agriculture, and craft beer with a 9-hole disc golf course right on site. Both spots are family-friendly, dog-friendly, and perfect places to relax and raise a glass to two days well spent rediscovering the treasures of Allegany County.
Why Play Tourist at Home?
Exploring your hometown with fresh eyes is more than just fun. It supports local businesses, connects you with community traditions, and reminds you of the beauty we get to enjoy every day. Allegany County may be where you live, but it’s also a destination that travelers from across the country seek out for history, scenery, small-town charm, and some of the best things to do in Frostburg and Cumberland, MD.
This fall, swap the suitcase for your favorite sweater and spend a weekend rediscovering the magic of Mountain Maryland, because sometimes the best adventures are waiting just down the street.