Events in Cumberland today

Toddler Play Date at Frostburg Library offers open play where young children can explore toys, look through picture books, and enjoy coloring, creating easy opportunities for kids to make friends while parents and caregivers connect. The gathering happens in the library’s play area for children. Registration is not required, and an adult must remain with each child.

Spend time reading aloud with Mika the dog in a calm, encouraging setting. Children can practice at a comfortable pace, make mistakes without pressure, and build skills through positive, low stress reading time with a friendly canine companion. The experience supports confidence, strengthens literacy, and turns reading into something enjoyable. Open to everyone who wants to experience the benefits of sharing stories with a furry friend.

Spend the morning golfing as part of Cumberland's Heritage Days. This public event welcomes everyone.

The Firemens Parade and Block Party teams up with the Spiker Brothers Memorial Car Cruise for a weekend filled with family activities, vendors, fire engines, cars, food, music, and more. Open to all.

This introductory karate class welcomes children ages 7 to 12 for a five-week program that teaches the basics of martial arts to beginners. Experienced instructors with more than 34 years of practice guide each session with a focus on skill building and positive habits. Participants are expected to follow five weekly dojo rules: keep the room clean, be respectful, be polite, avoid fighting with family members, and always try your hardest. Space is limited, so early registration is recommended. To be added to the official class list, call 301-689-8874. The initial class is free.

The 16th annual charity trail ride offers a full weekend of riding and camping to support Ride for Kids and the Pediatric Brain Tumor Foundation. Riders of every level can take part on designated A, B, C, and Pee Wee loops across two days of daytime trail riding. Overnight camping is available on site throughout the weekend, with additional lodging nearby in Romney. Motorcycle games add to the festivities during the weekend. Pricing includes a $5 gate fee, a $10 weekend camping fee, and a $40 weekend riding fee. Proceeds support the Ride for Kids Pediatric Brain Cancer Foundation. Registration and waiver information is provided by the organizers.

Pull on some boots and cozy flannels for Ivory Buck Boutique’s annual fall market. Enjoy a crisp-season atmosphere with artisan vendors, farm-fresh goodies, homemade baked treats, and food trucks. Discover unique gifts and browse the debut of the Fall Collection. Stroll among the pumpkins, sip something warm or iced, and take in the small-town country charm.

At the annual Heritage Days Festival, the Frostburg Elks will host a booth in support of Elks for Veterans. The Mermaid Pod from Cumberland, Maryland will offer face painting and glitter tattoos as a fundraiser, with proceeds helping the Elks for Veterans charity provide support to veterans. Characters from the pod will also be available for meet and greets and other interactive moments. COVID-19 safety measures will be in effect. If you are feeling unwell, please skip face painting and other services to protect volunteers and fellow attendees.

Bobcat Stadium hosts a matchup between Frostburg and Assumption. Last year’s home opener against Shepherd drew a full house, and that same lively atmosphere is the goal again. Tailgating is planned before kickoff, and organizers plan to arrange a postgame meetup at a bar.

Huckabay's PAK-Skater 2 returns to Dig Deep Brewing Co with a bigger follow up to the previous edition. Entry is $5, and all proceeds support the local animal shelter. Music comes from DJ Tyfecta, Heros Unsung, M60, Pawns Amongst Kings, and Mcrad. Anyone planning to skate must sign a waiver before getting started.

Mezzos hosts a country karaoke night led by DJ Blue Wave, offering a wide song selection that spans classic favorites and current hits. Pick up the microphone and sing the tunes you love while enjoying specials such as $2.50 domestic beers, $5 cocktails, and $2 shots, along with half-price artisan pizzas. There is no cover charge.

PCB brings its 2026 season to a close with a concert at Cumberland's Heritage Days Festival, performed in front of the Allegany County Courthouse.

This guided walk explores Cumberland’s past along portions of the city’s historic walking route. Setting out from Canal Place, participants visit notable landmarks and points of interest while hearing stories about the people, places, and events that shaped the community. The pace is family friendly with plenty of opportunities for conversation and photos. Highlights include Cumberland’s importance to American transportation, from its position at the western end of the C&O Canal to its growth as a center for railroads, industry, and westward movement. Only a selection of stops is included to keep the outing manageable. Public restrooms are available at Canal Place before the tour begins. The route follows sidewalks and downtown streets, so younger children should remain with their families. Strollers are welcome, though some sidewalks and crossings may require extra attention. Participants should come prepared with comfortable walking shoes, water, a packed lunch, and weather-appropriate clothing. After the walk, the group heads to a nearby playground to enjoy lunch and give children time for free play, offering an easy chance for homeschool families to connect.