With scenic overlooks, world-class bike trails systems such as the Great Allegheny Passage and C&O Canal Towpath (both recent USA Today 10Best Recreational trail systems), tree-lined scenic byways through some of the area's historic towns, over 150 miles of developed trail systems, and 70,000 acres of public land, there are plenty of opportunities to experience fall. As the crisp mountain air rolls in to bid farewell to summer, be sure to add these items to your fall bucket list, whether you live here year-round or you're just stopping through for prime leaf-peeping season. 


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


Hop aboard the Western Maryland Scenic Railroad, where you'll ride through the colorful mountain of changing leaves, including Maple, Oak, American Sycamore, and Locust trees, on a 3 ½-hour round trip heritage train excursion. Starting and ending at the historic railway station in downtown Cumberland, passengers will enjoy a 90-minute layover to explore the mountain town of Frostburg.  Or, ride the rails a different way with Tracks and Yaks, Maryland's first rail biking excursion, where you start in Frostburg and leisurely pedal your way on custom aluminum railbikes through iconic mountain views, including the famous Helmstetter's Curve.


Fall Cycling


With access to two world-class trails, the Great Allegheny Passage and the C&O Canal Towpath, and ideal road riding conditions with low traffic, cyclists love the routes available here in Mountain Maryland. Routes will take you into rural areas that showcase the natural beauty of our region. Find out just why the Great Allegheny Passage made the list for National Geographic’s 'Best Fall Trips' as you bike through this forest-lined rail trail, following the old Western Maryland railway bed between Allegany County's two trail towns, Frostburg and Cumberland. Be sure to explore our road routes with the Ride with GPS app, with mapped road rides to view the region’s stunning fall foliage by bike on the open road. And, for beginner mountain bikers and beyond, check out the vibrant treks on the mountain biking trails of Rocky Gap State Park and Green Ridge State Forest.


Family of five hiking in the fall.


Take advantage of Allegany County, the Mountain Side of Maryland’s access to 70,000 acres of public land and over 200 miles of developed trail systems for walking, hiking and connecting to nature. Rocky Gap State Park and Green Ridge State Forest offer close to 100 miles of hiking trails for nature lovers from the novice to the expert, with well-groomed to more rugged trails, all worth a visit for some fall colors. 


Dans Rock Overlook in the Fall_Midland MD

Photo by Bill Merlavage



Here in the mountains, there are many points that make you feel like you are on top of the world, literally. Our scenic overlooks provide stunning vistas of rolling mountains and views of up to four different states from one spot. 


Dans Rock Overlook

One of the most iconic overlooks in Allegany County,  Dans Rock is a 300-million-year-old rock that sits at the highest point in elevation in the county and features the most stunning views of the Allegheny Front.


Canyon Overlook

This overlook in Rocky Gap State Park can be accessed from the quarter-mile-long Canyon Overlook Trail and offers magnificent views of a mile-long gorge.


Town Hill Overlook

Located along the Historic National Road in Little Orleans, MD, the Town Hill Overlook offers extensive views of the eastern slopes of Green Ridge State Forest, Sideling Hill, and in the spring and fall migration season, this is a popular site to spot Golden Eagles. 


Point Lookout 

Offering a panoramic photo opportunity, Point Lookout reveals rolling mountains of Maryland and West Virginia and the Potomac River. 


Fall Colors on the Byway_Flintstone MD

Photo by Cherie Shoemaker



Home to Mile Marker "0" of the Historic National Road, America's first federally-funded highway, Mountain Maryland is the perfect place to plan your next road trip to find inviting views, magical main streets, enduring history, and engaging places. Hop on one of our scenic byways or engage with one of our history, food, or beverage trails to experience the magic of fall from the comfort of your car.




Fall is the perfect time to squeeze in one last paddle before the falling leaves turn to snow. Lake Habeeb at Rocky Gap State Park offers rentals for kayaks, canoes, and stand up paddleboards and has the picturesque surroundings of the beautiful fall mountains. The Potomac River, forming the southern border of Allegany County, sits adjacent to many forested banks, perfect for paddling to catch the fall color.




Fall is always a bustling time on the mountainside. Music, arts, and heritage areas are often at the forefront of fall festival season. Throughout the season, embrace the mountain culture with our Appalachian Festival, Heritage Days, or the annual Frostburg Fall Arts Walk. Enjoy mountain-made brews during Toasted Goat's Goat'oberfest, or capture some mountain heritage with museum tours and native plant sales at Evergreen Heritage Center's Fall Harvest Open House.


A latte served in a white cup sits on a table next to a vase with orange and yellow flowers.


Stop by Clatter Coffee for a twist on a fall-time favorite with the Great Pumpkin Latte, complete with homemade spiced REAL pumpkin, beginning on the autumn equinox. Other fall favorites from Clatter include the Local Maple Latte, made with maple syrup from Allegany County’s own S&S Maple Camp in Corriganville, MD, or the Apple Chai-der, made with apple cider steamed with masala chai. While you're at it, the Mountain Side of Maryland has a whole trail of treats that will warm you on a crisp fall day along the Donut and Go - Donut and Coffee Trail




Allegany County features three stunning mountainside golf courses, including the Jack Nicklaus Signature Course at the Rocky Gap Casino Resort, which was named one of Golfweek’s “Best Courses You Can Play in Maryland" in 2019! Relax and enjoy a round on any of the three courses, surrounded by spectacular fall scenery.




Grab your pole and tackle box, pack up a little cooler, and head outside to some of Allegany County’s favorite fishing holes! With the Potomac River forming the southern border of the county and the sloping hillsides that make up the Allegheny Mountain Range, the creeks, rivers, and waterways that flow through the mountains are the perfect place to cast a line and soak in the magic of fall.