Downtown Cleveland Holiday Window Decorating Contest

VOTING NOW CLOSED - CONGRATULATIONS TO THE WINNING BUSINESSES!

Thanks to almost 1,600 community votes across the 40+ participating businesses in Downtown Cleveland’s inaugural Holiday Window Decorating Contest, we’re thrilled to present the following winners, all voted upon by YOU.

1st Place: Masthead Brewing Co. (receiving the $500 Grand Prize)
2nd Place: Pizza 216 (receiving $150)
3rd Place: Society Speakeasy (receiving $100)

Thank you to every participating businesses for adding so much festive cheer downtown. Keep on supporting local businesses this holiday season and all year long!

Scroll down to view a gallery of all participating businesses, along with a Merry Map to show where each storefront is located. Click on each photo to view a full-size version, and be sure to stop by in person to check out each decorated display and stop into the businesses! Need some shopping inspiration along the way? Check out our 2025 Holiday Gift Guide, featuring many of these participating businesses!

Masthead Brewing Co.

Pizza 216

Society Speakeasy

Window Decorating Contest Merry Map

Use the digital Merry Map below to browse all participating businesses and plan your holiday stroll downtown. After exploring the decorated storefronts, vote for your favorite on the online poll. Each business will also have a flyer displayed in a storefront window that identifies them as an official participant and contains a QR code for you to scan with your phone to vote.

Interested in WinterLand Sponsorship?

Want to sponsor WinterLand? Get exposure from tree lighting day all through the season with our flexible options.

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