Itineraries and 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.
- Allegany County Fairgrounds
- Recurring every week day
Experience the Allegany County Fair, a cherished tradition! Discover our passionate local makers, gardeners, photographers, proudly present their creations. Feel the thrill of the Ferris wheel and be captivated by live performances that bring smiles to faces of all ages. Make…
- Recurring daily
The festival features world class regional and national acts spread out over 4 days. Most of the events are free! Come hear fantastic jazz in a fantastic setting, live and in person! Downtown Cumberland is a vibrant hub of activities, including live music, arts and entertainment…
- Mezzos
- Recurring daily
Savage Mountain Punk Festival is an annual three-day celebration of punk rock, marking its 11th year. Bringing big sound to a small town, the festival delivers an authentic, old-school punk vibe, honoring the roots of the genre while uniting fans, local music lovers, and rising…
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.
Get ready for a day filled with delicious sips and good vibes. Join us at Hoffman Park where the fun happens on Sunday, Sept 6th. This event is a celebration of all things craft beverages, from wines to brews to artisanal spirits all created and crafted in Maryland. Immerse…
Heritage Days is Cumberland's signature festival and has something for everyone - history, music, arts, crafts, festival food, children's activities - September 12 and 13, 2026. The schedule is subject to change. For the most accurate schedule, please visit…
- Frostburg State University
- Recurring daily
The Appalachian Festival will celebrate its 21st year on September 17-19, 2026, at Frostburg State University! Stay tuned for more details and follow along at their website - https://www.frostburg.edu/annual-events/afestival/.
- Western Maryland Railway Station at Canal Place
- Recurring daily
Maryland Railfest 2026 brings the rich history and excitement of railroading to life in the heart of historic downtown Cumberland. One of this year’s biggest highlights is the opportunity to ride behind the legendary steam locomotive No. 1309 on a special excursion to the scenic…
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…
