It’s National Plan for Vacation Day—a day dedicated to dreaming about your next great escape and making those plans a reality. Did you know that more than half of Americans don’t use all their vacation days each year? Let’s change that! This year, why not spend some of your hard-earned time off in Allegany County, the Mountain Side of Maryland?
Whether you crave outdoor adventures, culinary delights, cultural experiences, or scenic escapes, Allegany County has something for every traveler in every season. To celebrate the day and help spark your wanderlust, we’ve curated a list of 24 incredible things to do in Mountain Maryland—one for every hour of the day. From sunrise hikes to starlit dinners and everything in between, let this guide inspire your next 24-hour adventure in our mountain paradise.
1. Ride or Hike the Great Allegheny Passage
Take in the trail’s unique landmarks like Helmstetter’s Curve and the Mason-Dixon Line Park while biking or hiking. This iconic 150-mile rail-trail offers stunning natural and historical features accessible from Cumberland, Frostburg, and beyond. Learn More
2. Visit Lonaconing’s Historical Gems
Explore the Lonaconing Iron Furnace, a National Historic Landmark, and honor baseball great Lefty Grove at his nearby memorial park. Perfect for history buffs and families alike.
3. Soak in the Scenery with Tracks and Yaks
Ride custom aluminum rail bikes along the historic Western Maryland Railway line with Tracks and Yaks, Maryland’s only rail bike operator. Pedal through stunning mountain views, unique landmarks like Helmstetter’s Curve, and breathtaking scenery year-round.
4. Explore Public Art
Wander through Mountain Maryland’s Arts and Entertainment Districts in Cumberland and Frostburg, where outdoor murals and sculptures depict regional history and culture, blending creativity with the beauty of open spaces. Learn More
Photo Courtesy of DelFest
5. Celebrate DelFest
Experience DelFest, one of the nation’s premier bluegrass festivals, held each Memorial Day Weekend in Cumberland. Enjoy four days of world-class music and family-friendly fun, celebrating the rich legacy of Del McCoury in a unique and welcoming atmosphere.
6. Take the Scenic Overlook Driving Tour
Drive through the breathtaking Green Ridge State Forest on a 45-mile journey to spectacular overlooks that showcase Mountain Maryland's rugged beauty. Learn More
7. Ride the Western Maryland Scenic Railroad
Climb aboard the Western Maryland Scenic Railroad for a journey through history and stunning mountain landscapes. Whether you’re enjoying a family-friendly excursion, a romantic dinner train, or a seasonal adventure like the Polar Express, this year-round attraction offers unforgettable views and experiences for all ages.
8. Go Fishing in Mountain Streams
With the Potomac River and countless mountain creeks, anglers can find serene spots to cast their lines amidst breathtaking surroundings. Learn More
9. Shop at Allegany County Farmers Markets
Taste the flavors of the region by visiting farmers markets May through October, with live music, fresh produce, and handcrafted goods at Canal Place every Thursday. Learn More
Photo by Alicia Booth
10. Visit the Toll Gate House
Discover the history of America’s first highway system at LaVale’s seven-sided toll gate house, the last remaining one in Maryland.
11. Explore the C&O Canal National Historical Park
This iconic park is one of America’s most-visited national parks, featuring a rich blend of history, nature, and opportunities for hiking, biking, and birdwatching. Learn More

12. Honor the Coal Miner Memorial
Pay tribute to the miners who built the region’s industrial backbone at this immersive memorial in Frostburg, complete with views. Learn More
13. Attend Free Festivals and Concerts
From the Levitt AMP Cumberland Music Series in summer to fall’s Heritage Days Festival, enjoy live music and culture throughout the year. Learn More
14. Visit Local Art Galleries
Explore Mountain City Traditional Arts in Frostburg, the Ferleman Gallery, and the Gilchrist Gallery in Cumberland for an eclectic mix of Appalachian crafts and fine art.
Photo by Megan Henderson
15. Stargaze at Dans Rock
Visit the highest point in Allegany County for unbeatable views of the night sky and surrounding landscapes steeped in local lore. Learn More
Photo by Steve Dean
16. Drive the Scenic Byways
Follow Maryland’s scenic byways for inviting views, historic main streets, and unforgettable road trip moments in Mountain Maryland. Learn More
17. Take a Historic Walking Tour
Explore 32 historical landmarks in Frostburg or Cumberland, uncovering stories of architecture, community, and culture along the way.
Photo by Steve Dean
18. Walk to the Paw Paw Tunnel
Experience engineering marvels on the C&O Canal Towpath at the 3,118-foot Paw Paw Tunnel. Bring a flashlight for an eerie but exciting journey.
19. Try Rock Climbing at Rocky Gap
Whether you're a beginner or seasoned climber, Rocky Gap State Park offers crags for every skill level in a stunning mountain setting.
20. Enjoy Dog-Friendly Adventures
Hike, paddle, and even swim with your furry friend at Rocky Gap State Park, where dog-friendly trails and beaches await.
21. Tour the Evergreen Heritage Center
Roam the historic 130-acre farm, which includes museums, gardens, and trails, offering an insightful journey into Appalachian history. Learn More
22. Visit the Allegany Museum
Journey through the history of American transportation milestones at the Allegany Museum. Kids will love the interactive exhibits, and adults will marvel at the stories of the National Road.
23. Marvel at Town Hill Overlook
Enjoy panoramic views of Maryland, Pennsylvania, and West Virginia at this historic marker, just steps from the charming Town Hill Bed & Breakfast. Learn More
24. Capture Iconic Photos
From Helmstetter’s Curve to the Daisy donkey statue in Cumberland, Mountain Maryland offers countless picture-perfect locations to showcase your photography skills.
And guess what? We have not even covered half of it! There are incredible food trails, destination restaurants and retailers, historical attractions and monuments, trails, and a lengthy list of outdoor recreation all waiting to be discovered and explored. So, while we have your attention, give our website some time, and we hope to inspire you this 2025 travel year with time well spend in the Mountainside.