Allegany County, the Mountain Side of Maryland, celebrates this holiday season with its Shop Small, Win Big campaign, running through December 21, 2025. The festive promotion invites residents to explore independently owned local businesses and enter to win part of $1,000 in cash prizes.
Businesses across the county feature creative gifts and experiences that make holiday shopping delightful and meaningful. Explore the tinsel-adorned offerings at featured businesses below, and submit your receipts here to enter the raffle and see how far $50 stretches downtown, whether you seek unique presents or memorable local experiences. Ideas include:
Frostburg Finds
For those interested in hands-on experiences, Frostburg Fiber Depot offers classes in sewing, knitting, and crocheting for all skill levels. This holiday season, give a gift that’s both personal and locally made, or give the joy of a creative experience.
With weekly flavor lineups, custom dessert orders, and a stocked case of assorted treats, Baker Babes gives shoppers plenty of ways to bring home something special (and sweet) for holiday celebrations. Their treats also make thoughtful additions to holiday gift bags, host gift baskets, or workplace celebrations.
Wholesome Harvest Co-op consistently gives back to Frostburg residents in need. The co-op, which is community-owned and supports local farmers, offers $10 meal vouchers and $40 healthy food bags, allowing shoppers to pay it forward. Visitors can also support the cause by purchasing from the community kitchen, placing holiday pre-orders, or dropping off food donations.
Cumberland Highlights
Hometown Hobby Sports in Cumberland is a haven for collectors and memorabilia enthusiasts. Shoppers can find items that range from vintage sports collectibles to niche trading cards. If you’re searching for that missing piece to add to a treasured collection, look no further!
The Embassy Theatre offers more than entertainment; it’s a community hub where local talent shines on stage. The non-profit theatre, run almost entirely by volunteers, presents holiday productions including Plaid Tidings and the NYE Smileys’ Cabaret. Supporting the arts during the holiday season empowers the community, fosters creativity, and ensures local voices have a place to be seen and heard.
City Lights: An American Grill and Bar is a destination for fresh seafood, hand-cut steaks, pasta, and homemade desserts. From daily lunch orders to holiday team meals, City Lights has the atmosphere and the offerings your family and colleagues are sure to enjoy.
Canal Place Experiences
Visitors to Charis Winery & Distillery can enjoy tastings, tours, and locally crafted wines and spirits, making it a perfect stop for holiday gifts or festive experiences. Stop in to learn the story behind Cumberland’s first winery and enjoy seasonal sips in great company.
Wheelzup Adventures offers guided bike rides, hikes, kayaking, and a curated selection of outdoor gear and apparel, equipping visitors for adventures in every season. As a family-run business that is passionate about Allegany County’s recreational offerings, Wheelzup is a local resource for nature lovers of all ages.
Give Local, Give Unique
By exploring what Allegany County offers, holiday shoppers enjoy a diverse mix of products and experiences while supporting the local economy. Whether picking up collectibles, sampling fine wines, catching a theatre show, or enrolling in a creative class, small-business shopping fosters economic growth and community resilience.
To learn more about local businesses, discover how they make an impact, and find ways to support Allegany County entrepreneurs, visit our blog. For business development resources at any time of the year, contact us at alleganyworks@alleganygov.org. Frequenting local businesses creates meaningful holiday memories and helps sustain the region's thriving business community all year long!
