Itineraries & Trip Ideas
A one-stop place for Mountain Maryland road trip and itinerary ideas.
Explore our Scenic Byways
Home to three of Maryland's collection of scenic byways that offer inviting views…
NEW Downtown Cumberland
Come, see, and explore this new downtown destination.
Cool off, chill out, roll on! Looking for a fun family outing this summer? Choose from three scheduled departure times: 5 PM, 6 PM, or 7 PM, with seating available for all ages in both Coach and Open-Air cars. Upon arrival and check-in at our beautiful downtown Cumberland…
- Allegany Museum
- Recurring daily
The 2025 Mountain Maryland Plein Air Competition and Exhibition, June 9-15th, 2025, at Cumberland’s Allegany Museum through the partnership of the Allegany Arts Council and the Mountain Maryland Plein Air Committee. Other events at Arcadian Gallery and the Gilchrist Gallery…
- Recurring daily
Mountain Maryland Museum Week is a 10-day promotion celebrating Allegany County, the Mountain Side of Maryland's three centuries of American history. We invite you to travel back in time as you explore our museum attractions and history and heritage-focused experiences…
A celebration of great wings, cold drinks and country music!
Join Mountain Maryland for the annual Cumberland Garden Club Tour on Saturday, June 21, 2025! Embark on a self-guided journey through some of Cumberland's most enchanting private gardens. Discover stunning blooms, innovative landscaping, and unique outdoor spaces that will…
The annual festival, now in its 25th year, will be held on Saturday, June 28, 2025, on the grounds of the former Oldtown School located at 19210 Opessa Street, SE. The festival blends the history of Oldtown, founded by Thomas Cresap in 1741, with many family-oriented activities…
- Canal Place Heritage Park
- Recurring daily
The festival will be held June 25-29, 2025, at Canal Place in downtown Cumberland, MD. Wednesday • June 25 Bowling at White Oaks | 5:00 pm - 9:00 pm Thursday • June 26 Speak Their Names Vigil at Corner Tavern | 7:00 pm Stonewall Social at Corner Tavern | 9:00 pm Friday • June 27…
Frostburg Elks 48th Annual Derby Day. July 4, 9:30 AM. Over sixty entries will be racing on Main Street, starting at the Frostburg Library. Drivers are ages 9 thru 14. Experience your childhood & cheer all the drivers
21st Annual XTERRA EX2 Escape the summer city heat and head for the mountains! Join us at Rocky Gap State Park in Flintstone, MD for the 21st annual XTERRA EX2 Off-Road Triathlon, Duathlon, and Relay. Race Date: Sunday July 13, 2025 Start Time: 9:00am Location: Rocky Gap State…
Joe Nichols live in concert at the Allegany County Fair, July 15, 2025, at 8:00 PM. Doors open at 6:30 PM.
Don’t miss the sensational Anne Wilson in concert! Anne is a force in Contemporary Christian Music and Country. GRAMMY-nominated, with Dove and K-LOVE Awards, she’s a trailblazer breaking barriers. Anne’s music and bestselling book, “My Jesus: From Heartache To Hope,” has…
Live Music Event with multiple stages, vendors, and bands to unite the local music community. Nonstop Music! Nonstop Food! Nonstop Good Time! to support local Non-Profit Organizations.
The Western Maryland Craft Beverage Festival is back for 2025! And there's no better way to top off your summer and your glass with the best Maryland has! Get ready for a day filled with delicious sips and good vibes. Join us at Hoffman Park where the fun happens on Sunday, Aug…
Heritage Days is Cumberland's signature festival and has something for everyone - history, music, arts, crafts, festival food, children's activities - September 13 and 14, 2025.
The 20th Annual Appalachian Festival is September 18-20, 2025, at Frostburg State University! Thursday, September 18, will kick off the weekend with the annual Film Festival at the Palace Theatre on Main Street. Friday, September 19, will feature the annual Symposium which will…
The Dragons On The Lake Festival is the Cumberland YMCA's signature fundraising event. A unique sporting event that brings a community together for some friendly competition. Participants rave about the excitement, diversity, and community spirit surrounding the event. Teams of…
Places To Stay
A memorable getaway starts with a great place to lay your head at night, and Allegany…
Eat & Drink
You have heard the saying, 'the way to one's heart is through their…
Camping & RV Parks
Enjoy campsites and RV parks with full amenities and hookups all the way to primitive…
Shopping
Shop small year-round in communities like ours. With two designated Main Street…
