StaysBed & Breakfast
1878 Riverrun Bed and Breakfast
Bed & Breakfast in Hancock.
Bed & Breakfast
For two
Cumberland date night
A dinner that takes its time, a drink somewhere with brick and low light, and a walk that makes the evening feel longer than it was.
The short list
Pulled from the guide, best-rated first.
After Dark
Devils in The Detailing
After Dark in Frostburg.
12114 Kemp Dr NW, Frostburg, MD 21532, USA
StaysBed & Breakfast
1828 Trail Inn Bed & Breakfast
Relaxed guesthouse featuring cozy rooms with old-world accents, plus a porch & river views.
Bed & Breakfast
Eat & DrinkHamburger Restaurant
Allegania
Hamburger Restaurant in Cumberland.
Hamburger Restaurant
History & MuseumsArt Gallery
Ferleman Gallery
Art Gallery in Cumberland.
Art Gallery
StaysCampground
Glamping Clear Spring Maryland 3-Cabin Campground
Campground in Clear Spring.
Campground
AttractionsPerforming Arts Theater
Mountain City Creative Academy
Performing Arts Theater in Frostburg.
Performing Arts Theater
On the calendar
Events that suit this kind of day.
Annually over Memorial Day weekend (late May)
DelFest
DelFest is a multi-day bluegrass and Americana music festival founded by Del McCoury, held annually at the Allegany County Fairgrounds over Memorial Day weekend, featuring national touring acts, camping, and family activities.
Summer weekends (schedule varies by year)
Rocky Gap Casino Lakeside Summer Concert Series
Rocky Gap Casino Resort hosts a summer outdoor concert series on its lakeside stage overlooking Lake Habeeb, bringing touring musical acts to the resort grounds within Rocky Gap State Park.
A weekend in September
Heritage Days Festival
Cumberland's Heritage Days Festival brings food trucks, arts and crafts vendors, live music, and historic re-enactments to downtown to mark the start of the fall season, per Cumberland Main Street.
Annually around July 4th
Cumberland Independence Day Celebration & Fireworks
Canal Place in downtown Cumberland hosts the city's Independence Day celebration, including live music and a fireworks display over the C&O Canal National Historical Park area.
Year-round, multiple productions per season
Cumberland Theatre Season
The Cumberland Theatre presents a year-round season of professional and community stage productions, from musicals to dramas, with subscription packages for regular patrons. The 2026 season lineup is published on the theatre's own site with season-subscriber pricing options.
Throughout summer (dates vary; see Main Street Frostburg calendar)
Frostburg Main Street Summer Events
Main Street Frostburg organizes a series of summer community events in the historic downtown business district, including markets, live music nights, and seasonal street festivals supporting local shops and restaurants.
Good to know
Book the kitchen, not the bar
Downtown kitchens fill on Friday and Saturday; the bar side usually walks in fine.