Summer Festivals and Events

The Cumberland Living Arts Festival will take place on Baltimore Street in downtown Cumberland on Saturday, May 16. The street will be blocked off for arts vendors and kids' activities. The festival's mission is to establish a space where the creative community of Cumberland can…

Before the festival gates open, the music will take over Downtown Cumberland. Join us for a free one-night street celebration featuring DelFest ambassadors performing cover songs we all know and love. Experience the spirit of DelFest in the heart of downtown with live music…

• Allegany County Fairgrounds
• Recurring daily

The best in Bluegrass & Roots music return to Cumberland, MD on May 21-24, 2026! DelFest was created to be a family-friendly music festival honoring Del McCoury. On-site you’ll find incredible music all day long on our Grandstand Stage, intimate Artist Playshops, Late Night…

• 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…

• Allegany County Fairgrounds

The Tri-State Wing-Off and Music Festival is a lively, family-friendly event that celebrates the best of local flavors, music, and community spirit in the tri-state area. Centered around a friendly wing-eating competition, the festival brings together food enthusiasts to sample a…

The 26th annual Oldtown Summerfest will be held on Saturday, June 27, 2026, 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 activites…

• Canal Place Heritage Park

Join us for a free community celebration at Canal Place and throughout the County, on July 4th from 2pm until after the conclusion of fireworks (approximately 10pm) We will celebrate the MD250 / America250 all day as we explore our unique history and heritage. Live entertainment…

Frostburg Elks 49th 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

Join the Children's Literature Centre this summer for a day of scallywagging fun! This free event gives children the opportunity to play pirate games, make pirate crafts, and hear a presentation from an author or illustrator as they come to Frostburg to share a summer themed…

• Hoffman Park Disc Golf Course

Get ready for the SIXTH ANNUAL Western Maryland Food Truck Festival by Station 3 Solutions, benefiting Averey's Change-up Foundation and Allegany County Animal Shelter

• Rocky Gap State Park

Escape the summer city heat and head for the mountains! Join us at Rocky Gap State Park in Flintstone, MD for the Rocky Gap Off-Road Triathlon, Duathlon, Aqua Bike, and Relay (formerly XTERRA EX2). Race Date: Sunday July 12, 2026 Start Time: 9:00am Location: Rocky Gap State Park…

• 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…

• Allegany County Fairgrounds

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.

• 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…

• Hoffman Park

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…