Events in Cumberland, MD

At the Washington Street Library, toddlers can enjoy unstructured, free play with toys, books, and scavenger hunts. The event provides a space for children to make new friends while parents connect. No registration is required.

Now in its 21st year, this Appalachian Festival fills Frostburg State University with film, conversations, music, dance, arts, and community. The celebration begins with a Film Festival at the Palace Theatre, followed by a symposium on the Upper Quad featuring a range of speakers. The festivities then gather momentum on the Upper Quad with free performances and activities, including regional and bluegrass music, community brass ensembles, traditional Appalachian dance, heritage arts and crafts, cultural programs, Appalachian food, children’s activities, local artisans, environmental education, and more. A capstone concert at the Palace Theatre concludes the celebration, with tickets available through the FSU Cultural Events Series. Additional details will be shared soon.

At Mountain City Center for the Arts, kids can dive into a Descendants and Zombies themed Kids Night Out filled with music, movement, creativity, games, and plenty of monster fun. Dressing up is encouraged, so participants are welcome to arrive as a favorite character inspired by those stories. The evening features a high energy dance party, engaging games, hands-on arts activities, snacks, and other surprises, inviting monsters, villains, werewolves, zombies, and supernatural stars to celebrate together. The program is designed for grades K through 6 as a kids only experience. A Mini & Me option is available for ages 2 to 4 who attend with at least one adult, with up to two adults welcome, and adult tickets are not required. Whether cheering for Zombies, backing Descendants, or simply ready for the party, it is a chance to dance, create, play, and make new friends.

This signature sporting festival buzzes with energy, friendly rivalry, and a strong sense of community. Teams of all ages and experience levels take part in an inclusive setting that welcomes a wide range of participants. Success comes from timing and finesse rather than brute force, which makes it a standout team-building experience. Participants consistently highlight the diversity of the field and the uplifting spirit that surrounds the event.

Tri-State Concert Association presents a four-artist special concert at Ali Ghan Shrine Club featuring The Cowsills, Brian Hyland, The Cyrkle, and Dennis Tufano. This showcase brings all four acts together on one stage for a single program.

Meet Briana in person at the Mad Hatter Bistro & Lounge and the Chicago Market Gallery. Enjoy a relaxed chance to say hello and see her at these two locations.

A relaxed late summer nature walk explores a short out-and-back stretch of the Great Allegheny Passage between Frostburg and Cumberland, beginning at the Frostburg Train Station. The distance will be about 2 to 4 miles, with the turnaround point chosen by group consensus. Before heading out, the group will pause to view and discuss the Coal Miners Memorial installed at the depot last year. This route is level, well maintained, and a mix of gravel and paved surfaces, making it approachable for all experience levels. Parking is available either at the GAP trailhead below the switchbacks or up top near the Trail House Inn and Carriage Museum, with the meetup by the train loading area at the top. Come prepared with sturdy footwear, comfortable layers, bug spray, and plenty of water, and expect ample tree cover that offers cooling shade. A first aid kit will be available, but each participant is responsible for personal preparedness and safety. RSVPs are requested, and punctual arrival helps ensure no one misses the group. Weather updates and any potential cancellation will be shared in advance if conditions require, and there is no rain date. Leashed dogs are welcome; bring water for pets and include them in your RSVP so dog introductions can be coordinated at the trailhead.

Enjoy a relaxed nature walk along the Great Allegheny Passage Bike Trail, designed for families who want to explore together. Take in fresh air and scenic views while watching for wildlife, collecting interesting leaves, and encouraging curiosity, whether that means asking questions or letting kids run ahead on the trail. This is an informal community meetup, not a led program, so everyone is free to set their own pace and decide how long to stay. Bring water and wear comfortable walking shoes, and consider a camera, binoculars, or a nature journal if you would like. It is a simple way to connect, explore, and spend time outdoors together.

Get ready for 200 foot drags across nine classes with a 100 percent payout and a First Round Callout. Spectator admission is $10, and children 12 and under are free. Seating is not provided, so bring chairs. $10 test runs are available on a first come, first served basis. The day follows a clear flow with gates opening, a registration cutoff, a drivers meeting, and then the first race. Camping lots are available, and there are openings for vendors.

Cyclists take on a steam locomotive in a timed climb from Cumberland to Frostburg along the Great Allegheny Passage, riding beside the Western Maryland Scenic Railroad’s 1309 as it tackles Mt. Savage. The course spans 15.3 miles, turning the ascent into a showdown of stamina, steel, and steep grades. Participants may compete solo or in teams of up to six, with staggered starts. The train’s climb is officially timed, and anyone who posts a faster ascent earns a commemorative engraved railroad spike. All riders receive a souvenir race T-shirt. An awards ceremony follows the train’s arrival in Frostburg, and food and drinks are provided for riders and guests. Proceeds support maintenance and development of the Maryland section of the Great Allegheny Passage and help advance new trail projects. The event is hosted by Mountain Maryland Trails, a volunteer nonprofit working with Allegany County Government to promote, maintain, and expand local trails. The Great Allegheny Passage begins at mile zero in Cumberland and stretches through the Alleghenies to Pittsburgh, offering 150 miles of off-road adventure.

The seventh annual Baskets & Brews fundraiser features basket raffles, beer sales, food trucks, a 50/50, music, tip jars, and vendor booths. To offer more room and seating, this year’s event takes place at the Ali Ghan Shrine Club Picnic Grounds, following six years of support and hosting from 1812 Brewery. Cash is required for all paper gambling. Cards are accepted for basket raffles, beer, and Friends Aware merchandise, with a standard 3% transaction fee. Outside food and beverages are not permitted.

Wrap up the 2026 Queer Out Here nature walk series with a 4.2 mile loop on the Twin Oaks Pine Lick Trail in Green Ridge State Forest. The route is welcoming to determined hikers and offers plenty of shade beneath the trees. Plan to meet at the Twin Oaks Pine Lick Loop trailhead and be ready to start promptly. RSVPs are requested to help coordinate the group and an on time departure. After the hike, an optional stop at Locust Post Brewery is planned to celebrate the season, share feedback on the year’s trails and meetups, explore ideas for 2027, and discuss a possible camping or outdoor winter event. Leashed dogs are welcome, and participants are asked to RSVP their pups so greetings can be coordinated at the trailhead. Come prepared with sturdy footwear, weather appropriate clothing, bug spray, and enough water to stay hydrated. A first aid kit will be available, and each hiker is responsible for personal preparedness and safety. Weather updates and any cancellation will be shared in advance, with a rain date planned.

Fall Bingo Blitz returns for its second year as a lively fundraiser benefiting CASA of Western Maryland. Enjoy 20 rounds of bingo alongside vendor booths, themed prize giveaways, and tip jars. Concessions including hot dogs, soft drinks, and snacks will be available for purchase. An early-bird ticket is priced at $25, increasing to $35 after the early-bird period. The event takes place at City Place in Frostburg, with the venue sponsored by the City of Frostburg. Proceeds support the recruitment and training of volunteers who speak up for abused and neglected children. For more information, call (301) 777-1262 or email advocate@casaofwesternmaryland.org.

On the main floor of the Lewis J. Ort Library, Special Collections librarian and archivist Liza Zakharova will lead a history talk centered on the presidency of Dr. Herb F. Reinhard Jr., spanning 1986 to 1991. The program highlights FSU community figures, key events, and notable accomplishments from his tenure. Admission is free.

The Bobcat Hall of Fame Induction Ceremony at Frostburg State University features a cocktail hour followed by dinner. Activities take place in the Upper Lobby and ARMAH, LUC. Admission is $35 for adults and $15 for children 12 and under. Reservations are required.

Young female grapplers can take part in a dedicated seminar led by Clara Huon. Clara trains at Foundry Jiujitsu, holds a juvenile blue belt, and is a 2026 Pans and Worlds champion. The session offers two hours of focused instruction at Ryoma Academy of Martial Arts, LLC. Participants ages 5 and up are welcome. Vendors will be on site and grab bags will be available.

This family-friendly screening features minions and monsters. Admission is free, and complimentary snacks will be available.

The 18th annual Ghouley Pub Crawl, pronounced to rhyme with Hooley, is a Halloween celebration across Downtown Cumberland, Maryland. Attendees dress in costume and move with friends from place to place for a night of Halloween-themed pub crawling in the heart of downtown.

A returning event promises a lively experience. Building on a previous outing that was full of fun, the organizers hope to welcome familiar faces along with many more newcomers. The aim is to make it even more enjoyable and create a packed, high energy atmosphere.