WinterLand Kickoff

November 29, 2025 | 12-5:30 PM | Public Square

Jump into the Holiday season with the WinterLand Kickoff at Public Square! Bring your family and friends for music, food, entertainment, holiday activities, and light shows. Take pictures with Santa, roast s’mores over the firepits, and take a lap around the ice rink!

Programming: 12-5:30 PM

12pm S’mores*
12-4pm Trackless Train Rides
12-5pm Food Trucks
12-5pm Firepits
12-5:30 Music & Live Entertainment Onstage
- 12pm-5:30 DJ Kyro & Live Games
- 3pm Da Land Brass Band
- 4:30pm Apostle Jones
12-5pm Games & Activities at the Jingle Bell Tent
12-5pm Photos with Santa
12-10pm Ice Skating
2-5pm Photos with the Grinch
3pm Hot Chocolate
Downtown Cleveland partners will also be on the Square to spread holiday cheer, including:

GCRTA Holiday Trolley
Destination Cleveland Truck & Letters
Cleveland Public Library’s Story Walk
Soldiers’ & Sailors’ Patriotic Santa
Great Lakes Science Center

Ice Skating at the Cleveland Foundation Skating Rink

Noon-10PM

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Destination Cleveland’s IlluminateCLE Holiday Show Debut

Beginning at 5:30pm and repeating every 30 minutes until 11 p.m., this dazzling new holiday light show will debut with three original songs by local artists.

The 50-foot tree in Public Square will sparkle with synchronized lights, complementing the half a million additional lights around the Square.

A Walkable Holiday Experience

5th Street Arcade Maker Market

10AM-7PM

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Pop-Up Marketplace at Timeless Traditions

Noon-4PM

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Holiday Bars

All Day

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A Christmas Carol

1:30 and 7:30PM

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Cleveland Monsters Vs. Hartford Wolfpack

7PM

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Cleveland Public Library Merry Maker Fest

10:30AM-5:30PM

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A Motown Christmas

7:30PM

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Ekoostik Hookah at House of Blues

6PM

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Timeless Traditions - Modern Celebrations

All Day

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Twilight in Concert

8PM

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WinterLand Kickoff Map

Saturday, November 29th, Public Square will be bustling with activity. Please refer to the map to plan your visit to the WinterLand Kickoff

Road Closures

All roads around Public Square will be closed from 7:00AM Saturday to 12:00AM Sunday

Entrance Points

There are 5 designated entrance points to enter Public Square on November 29th. All minors must be accompanied by a parent or legal guardian (21+) to enter the Square. Individuals under the age of 18 without a parent or guardian will not be permitted into the event.