This weekend in Cumberland, MD

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.