November 29, 2025 | Noon-5:30PM | Public Square
WinterLand Returns!
Start the holiday season at the WinterLand Kickoff on Public Square!
Small Business Saturday
WinterLand takes place on Small Business Saturday, and there are plenty of options to get your shopping done while supporting local: Cleveland Bazaar Holiday Market in the 5th Street Arcades, Tower City, and across all of downtown!
Downtown Cleveland Holiday Window Decorating Contest
This holiday season we are creating bright and merry street corridors by incentivizing local businesses to decorate their storefronts. When you participate, you will receive free advertising across Downtown Cleveland’s social channels promoting your business as a must stop holiday destination. The public will vote for their favorite display. The winning storefront will receive a $500 cash prize!
Downtown Holiday Pop-Up Bars
Get ready to toast the holidays by sipping on festive cocktails, enjoying over-the-top decorations, and staying warm on cold winter nights at downtown Cleveland’s holiday bars! Grab your ugliest sweater and get in the holiday spirits by visiting these immersive Christmas-themed pop-ups. Don’t wait - they’ll only be here for a limited time through the upcoming 2025 holiday season!
Be a 2025 WinterLand Partner
Together, let’s showcase the magic of Cleveland in the Winter. We need your help in building a robust calendar of events for the Winter season. If your business or organization would like to become a WinterLand partner and host an activation for WinterLand Kickoff or throughout the rest of the Winter season, please fill out the form below.