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WinterLand

The Land's Official Holiday Kickoff

Date and Time

Saturday, November 28, 2026
Noon - 5:30 pm

Location

Cleveland Public Square
50 Public Square
Cleveland, OH 44113

Admission

Free

Contact

Email: dtcle@downtowncleveland.com

Phone: 216.736.7799

View Event Website

Jump into the Holiday season with the WinterLand Kickoff at Public Square! Bring your family and friends for music, food, entertainment and holiday activities. Take pictures with Santa, roast s’mores over the firepits, and take a lap around the ice rink! Plus, experience the brand new Illuminate CLE Holiday Light Show throughout the whole nights, paired with synchronized Christmas tree lightings every half hour from 5:30pm - 11pm.

Enjoy WinterLand at your schedule and pace, whether you're looking for a full afternoon of family fun, a night with holiday bars, ice skating and light shows or a mix of everything.

Events Rundown:

Trackless Train Rides (12:00 PM - 4:00 PM)

In partnership with the Cleveland Public Library’s Merry Maker Fest, climb aboard a festive train that drives right down the street! Loop around Superior Avenue between the Library and Public Square. 

DJ Kyro (12:00 PM - 4:30 PM)

Enjot upbeat music and live entertainment with DJ Kyro, the official DJ of the Cleveland Guardians.

Photos with Santa (12:00 PM - 5:00 PM)

Santa’s been busy making his list and checking it twice, and he’s ready to visit downtown Cleveland!

Firepits w/ S'mores and Hot Chocolate (12:00 PM - 5:30 PM)

Warm up around cozy firepits placed through the middle of Public Square along Superior Avenue. S’mores will be given away from the Public Square Hospitality Kiosk (adjacent to the skating rink, near Superior Avenue) and hot chocolate will be given away from the on-site Jingle Bell Tent.*(while supplies last)

Games & Giveaways (12:00 PM - 5:30 PM)

Have some fun at a variety of game stations with activities for all ages, and stop by activations from community partners to grab some festive giveaways. *(while supplies last)

Partner Activations on the Square (12:00 PM - 5:30 PM)

Check out the incredible partners of Downtown Cleveland including the Greater Cleveland RTA Holiday Trolley, Destination Cleveland, Cleveland Public Library Story Walk, Soldiers' & Sailors' Patriotic Santa, Great Lakes Science Center and Lutheran Metropolitan Ministry.

Food Trucks (12:00 PM - 5:30 PM)

Enjoy a variety of tasty food trucks in the Square throughout the day to grab lunch, snacks, or an early dinner before the Illuminate CLE light shows begin.

Ice Skating (12:00 PM - 10:00 PM)

Grab your friends and family, and go ice skating in the middle of downtown! Soak up the festive sights while skating to holiday music with this beloved WinterLand tradition.

Photos With the Grinch (2:00 PM - 5:00 PM)

Whether you’re on the naughty or nice list, the Grinch will also be making a special appearance on Public Square to take photos with families.

Da Land Brass Band (3:00 PM)

Featuring a modern take on New Orleans street bands with a high energy funk sound, Da Land Brass Band bridges the gap between musical tradition and a vision for the future.

Apostle Jones (4:30 PM)

Apostle Jones is a dynamic soul ensemble that bends styles and genres to create a uniquely collaborative energy and sound. Pulling from collective influences of rock, R’n’B, blues, gospel, and funk, the Apostles soar with original music and positive vibes.

First Illuminate CLE Holiday Light Show (5:30 PM)

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

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