November 29, 2025 | Noon-5:30PM | Public Square

WinterLand Returns!

Start the holiday season at the WinterLand Kickoff on Public Square!

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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!

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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!

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  • Skate Public Square

    Glide into winter fun at the Public Square Ice Skating Rink, Cleveland’s favorite spot for festive memories and frosty adventures!

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  • Downtown Cleveland Snow Days

    When downtown gets enough snowfall to cover the grass, Snow Days pop-ups will take place on the Mall B slope in the heart of Downtown Cleveland (next to Hilton Cleveland). Follow our social media accounts for updates when the snow starts falling!

  • Bright Nights at Public Square

    Weekends in December | Public Square

    Make the most of your weekends this winter at Bright Nights! Come to Public Square and enjoy ice skating, an outdoor bar, firepits, tasty s’mores, and holiday tunes!

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.

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