Witnessing the brilliant colors of autumn in Allegany County, the Mountain Side of Maryland is an unforgettable experience. With 70,000 acres of public land, scenic overlooks, historic small towns, and two world-class trails, there are endless ways to soak in peak fall foliage. Plan your trip for late September through mid-October when the leaves reach their most vibrant hues.
Take in the Views from Scenic Overlooks
From mountaintop vantage points to sweeping valley views, Allegany County is filled with overlooks that will make you feel on top of the world.
Canyon Overlook Trail – Rocky Gap State Park
A short, family-friendly hike with breathtaking views of Lake Habeeb and the surrounding ridges.
Point Lookout – Green Ridge State Forest
A sweeping view of a dramatic bend in the Potomac River.
Town Hill Overlook – Historic National Road
A road-tripper’s favorite, with panoramic views of rolling Appalachian mountains.
Dans Rock Overlook
One of the county’s most iconic viewpoints, offering vibrant vistas into West Virginia and Pennsylvania.
Drive Through a Sea of Color
For leaf peepers who prefer a leisurely drive, Allegany County delivers.
Green Ridge State Forest Scenic Driving Tour
A 44-mile loop through Maryland’s largest forest, with five designated overlooks.
Scenic Byways in Mountain Maryland
Each offers a mix of brilliant foliage, cultural landmarks, and charming small towns.
Ride the Rails (or Railbikes!)
Fall in Mountain Maryland is best seen by train—or railbike.
Western Maryland Scenic Railroad
A 3.5-hour heritage excursion with sweeping colorful views of Maple, Oak, American Sycamore, and Locust trees offers a 90-minute layover to explore the City of Frostburg, Marlyand.
Tracks and Yaks – Railbiking Adventure
Pedal along the same historic rail lines on custom aluminum railbikes, surrounded by brilliant fall colors and iconic views, including the famous Helmstetter’s Curve.
Explore by Bike
Cyclists flock to Allegany County each fall for the crisp mountain air, spectacular scenery, and world-class trails.
Great Allegheny Passage (GAP)
Mile zero begins in Downtown Cumberland, making Allegany County the gateway to one of USA Today’s 10Best Trails in North America.
C&O Canal Towpath
Ride through history on 48 miles of towpath that wind through Allegany County with river views, canal structures, and historic trail towns.
Mountain Biking in Allegany County
For those craving singletrack adventures, Allegany County offers a mix of flow trails and rugged routes:
- Constitution Park Trails (Cumberland) – new world-class flow trails with beginner-friendly routes and features like berms and jumps.
- Dans Mountain State Park – the Lonaconing Loop, a rocky 4.5-mile singletrack with a 650-foot elevation gain.
- Rocky Gap State Park – from the Lakeside Loop to the challenging Evitts Homesite Trail.
- Green Ridge State Forest – a 12.5-mile rugged circuit for seasoned riders.
Hike Through Colorful Forests and Historic Streets
Whether you crave a rugged backcountry trek or a downtown stroll, Allegany County offers hikes for every style.
Rocky Gap State Park & Green Ridge State Forest
Nearly 100 miles of trails ranging from easy to rugged, ideal for leaf season.
Historic Downtowns – Cumberland & Frostburg
Brick sidewalks, historic architecture, and tree-lined streets bursting with color.
Dine Outdoors with a View
After a day of leaf peeping, refuel in the crisp autumn air.
Downtown Cumberland, MD
Experience outdoor dining in Downtown Cumberland, where a reimagined streetscape blends modern design with historic charm. Enjoy al fresco meals with mountain views while exploring one of Western Maryland’s most vibrant dining districts.
Rocky Gap Casino Resort – Lakeside Grille
At Rocky Gap Casino Resort’s Lakeside Grille, dine on the terrace overlooking sparkling Lake Habeeb. In autumn, the surrounding hills of Rocky Gap State Park explode with color, creating one of the most breathtaking dining backdrops in Maryland.
Mountain Maryland Tap and Pour Tour
Sip seasonal craft beers in unforgettable outdoor settings. At 1812 Brewery, relax on the expansive patio or in the rustic loafing barn, often with live music and food vendors on weekends. Or head to Locust Post Brewery, set on a scenic 26-acre farmstead, where you can enjoy fresh pours and even play a round of disc golf with mountain views as your backdrop.
🍂 Pro Tip: Book your stay early! Fall is one of the busiest times to visit Allegany County, and lodging fills quickly.
One thing is certain: Mountain Maryland is the perfect place to catch peak fall foliage, whether from an overlook, a bike, a train, or a trail.