FOR IMMEDIATE RELEASE
Allegany County Office of Tourism
701 Kelly Road
Cumberland, MD 21502
aworkman@alleganygov.org
www.mdmountainside.com
Shop Local, Win Big: Allegany County’s Holiday Contest Returns for a Sixth Year
Mountain Maryland celebrates community spirit with $1,000 in prizes for holiday shoppers
November 20, 2025 – CUMBERLAND, MD – Allegany County Tourism is once again inspiring residents and visitors to keep their holiday spending close to home. The 6th Annual Shop Small, Win Big contest launches November 28 and runs through December 21, 2025, offering $1,000 in Visa gift card prizes to shoppers who support local, independently owned businesses across Mountain Maryland.
Participants can enter by shopping in-person or online (where applicable) at any participating small business in Allegany County and uploading their receipts to the Shop Small, Win Big holiday landing page: www.mdmountainside.com/winbig. Each qualifying purchase counts as an entry for weekly $50 Visa gift card drawings and the grand prize of $550, announced on December 22.
“The holiday season brings an incredible opportunity to strengthen our local economy,” said Ashli Workman, Director of Allegany County Tourism. “Our Main Street districts and small businesses are the heartbeat of Mountain Maryland. This campaign reminds everyone that when you choose local, you help our communities thrive.”
There is no minimum purchase required and no limit on the number of entries per person. Drawings for $50 gift cards will take place on December 4, 11, and 18, with the $550 grand prize drawing wrapping up the campaign on December 22.
“We want to reward those who shop locally and encourage them to keep reinvesting right here at home,” added Workman.
Allegany County is home to two Main Street Maryland communities—Cumberland and Frostburg—each filled with unique boutiques, restaurants, and specialty retailers. Following the $16.1 million redevelopment of Baltimore Street in downtown Cumberland, this year’s holiday season is the perfect time to rediscover both long-time favorites and new additions to the county’s business community.
Visit mdmountainside.com/winbig for a list of participating businesses, e-commerce links, and “Made in Allegany County” gift ideas.
The Shop Small, Win Big Contest is part of Allegany County Tourism’s ongoing efforts to support the local business community, in partnership with the Allegany County Chamber of Commerce, Canal Place Preservation and Development Authority, Cumberland Main Street, Downtown Cumberland Business Association, and FrostburgFirst.
Learn more or enter at mdmountainside.com/winbig.