When autumn arrives in Allegany County, Maryland, the mountains come alive with crisp air, fiery foliage, and cozy seasonal flavors. With 70,000 acres of public land, two world-class trails, tree-lined scenic byways, and charming small towns, there are endless ways to experience the magic of fall. Whether you’re planning a weekend getaway from DC, Baltimore, or Pittsburgh, or simply looking for the best fall getaways in Maryland, here are 10 can’t-miss activities, counting down to the ultimate fall experience.

 

10. Cozy Up in the Mountains

Night sky with the Milky Way - Frostburg MD - Megan Henderson

Photo by Megan Henderson

Start your autumn escape with a little comfort. Book a cabin in Rocky Gap State Park or pitch a tent in Green Ridge State Forest and spend your evenings around a crackling campfire. With crisp night air, starry skies, and s’mores in hand, you’ll feel the essence of fall in the mountains.

 

9. Shop Small Town Charm

A woman with a red hat and vibrant blue hair looks through a rack of clothing.

Fall is the perfect season for slow strolling through our historic downtowns. Browse Cauldron Vintage in Frostburg for unique vintage finds, treasure hunt for antiques at Fort Cumberland Emporium in downtown Cumberland, or explore the sprawling Queen City Flea Market with over 150 vendors. From antiques to boutique fashion, you’ll discover one-of-a-kind pieces while supporting local shops.

 

8. Seek Haunted History

Paw Paw Tunnel

What’s fall without a little fright? Allegany County’s storied past comes with its share of ghostly legends. Wander the eerie Paw Paw Tunnel, step into the shadowy basement of Hotel Gunter, or dine with history (and perhaps a spirit or two) at Puccini’s Restaurant. For more mysterious stops, see our full guide to Haunted History: Places to Visit for a Ghostly Good Time.

 

7. Fall on Tap

An amber beer being poured from a tap.

Raise a glass to the season at Allegany County’s breweries, where fall pours include pumpkin ales, Oktoberfest lagers, and spiced seasonals. Favorites include:

 

6. Sweet Treats of the Season

Clatter-Coffee-Frostburg-MD

Autumn means indulgence. Stop at AJ’s Cookie Jar in Cumberland for gourmet cookies like Pumpkin Caramel Snickerdoodle or Apple Crisp, along with seasonal French Macaron flavors such as cinnamon roll and vanilla chai latte. Pair them with a specialty drink from Clatter Coffee, like the Great Pumpkin Latte or the Local Maple Latte, made with syrup tapped right here in Mountain Maryland.

 

5. Catch a Fall Festival

Appalachian-Festival-Frostburg-MD

Celebrate the season Appalachian-style. From heritage to hops, there’s a festival nearly every weekend:

  • Appalachian Festival in Frostburg – Mountain traditions, bluegrass, and craft vendors.
  • Heritage Days in Cumberland – A street festival honoring local history.
  • Western Maryland Craft Beverage Festival – Sip, savor, and enjoy live music.
  • Western Maryland Artist Studio Tour – Step inside working studios across the county.

 

4. Go for a Paddle

Couple + Dog Canoe - Rocky Gap State Park - Flintstone

Extend summer just a little longer with a fall paddle. At Lake Habeeb, the glassy water reflects brilliant autumn ridges. Or float stretches of the Potomac River, where forested banks burst with color. It’s a peaceful way to see fall unfold from the water.

 

3. Take a Hike

A family looks over the railing at the Canyon Overlook in Rocky Gap State Park.

Explore more than 200 miles of hiking trails on the Mountain Side. From the rugged backcountry paths of Green Ridge State Forest to the lakeside loops at Rocky Gap State Park, every trail rewards you with sweeping fall views and the crunch of leaves underfoot. Pack a thermos of hot cider for the journey — it tastes better in the mountain air.

 

2. Hop on a Bike

Road-Cycling-in-Fall-in-Allegany-County-MD

Cyclists love Allegany County in fall. The Great Allegheny Passage (a National Geographic “Best Fall Trip”) and the C&O Canal Towpath both wind through forested corridors ablaze in autumn color. Prefer the open road? Use the Ride with GPS app to explore mapped backroads that showcase our rolling countryside. Mountain bikers will also find vibrant treks at Rocky Gap and Green Ridge.

 

1. Ride the Rails

An aerial view of a train docked at a small depot station surrounded by trees full of yellow fall leaves.

For the ultimate fall experience, hop aboard the Western Maryland Scenic Railroad. This 3 ½-hour round-trip excursion winds through the mountains at the height of color, offering breathtaking views of red maples, golden oaks, and the famous Helmstetter’s Curve. Or, try something new with Tracks and Yaks rail biking, pedaling along historic tracks framed by autumn’s fiery hues. Either way, riding the rails is the crown jewel of fall in Allegany County.

 

 

Plan Your Fall Getaway

From haunted history and sweet treats to rail rides and mountain trails, Allegany County, the Mountain Side of Maryland, is the perfect fall destination in the Mid-Atlantic. Just a few hours from DC, Baltimore, and Pittsburgh, it’s an easy escape filled with color, flavor, and adventure.