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.

Great-Allegheny-Passage-Truss-Bridge_Allegany-County-MD1. 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

 

Family Cycling - Iron Furnace Park - Lonaconing MD2. 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.

 

Four passengers peddle along a rail line on peddle bikes with the trees, sky and clouds in the background at sunset.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.

 

Climb and Glide - Sculpture GAP Switchback - Frostburg md4. 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

 

Billy Strings - DelFest - Knobley Mountain - Cumberland MD
​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.

 

A truck drives along a paved road during a sunny day with fall foliage along the roadside.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

 

Western Maryland Scenic Railroad - 1309 - Switzerfilm - Cumberland MD7. 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.

 

AlleganyCounty-Maryland-Fly-Fishing-Potomac-River8. 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

 

Farmers-Market9. 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

 

First Toll Gate House-Route 40, LaVale, MD
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.

 

CO-Canal-Towpath-in-Allegany-County-MD11. 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

 

Coal Miner Memorial - ED - Frostburg MD
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

 

Full band on stage playing music in front of a colorful backdrop that says "Levitt AMP Cumberland Music Series."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

 

Gilchrist Gallery - Blog Optimized - Cumberland MD14. 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.

 

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

 

Canal-towpath-approaching-Cumberland-MD
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

 

Reimagine Cumberland - Photo of Downtown Cumberland Mall17. Take a Historic Walking Tour

Explore 32 historical landmarks in Frostburg or Cumberland, uncovering stories of architecture, community, and culture along the way.

 

Inside the Paw Paw Tunnel - Paw Paw WV
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.

 

Rocky Gap Climbing - Woman Vertical - Flintstone MD19. 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.

 

Couple + Dog Canoe - Rocky Gap State Park - Flintstone20. 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.

 

Coal Trail - Evergreen Heritage Center21. 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

 

George-Washington-Exhibit-Crossroads-of-America-Allegany-Museum22. 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.

 

Little Orleans-MD-Scenic Overlook23. 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

 

Woman taking a picture of a green mountain vista from a cliff-top.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.