Downtown Cleveland, Inc Unlocks Holiday Magic with WinterLand Kickoff on Saturday, Nov. 29

Written By Julia Matter

WinterLand returns to the heart of the city on Saturday, Nov. 29, as Downtown Cleveland, Inc., in partnership with presenting sponsor K&D, hosts its annual kickoff to the holiday season on Public Square. The beloved tradition brings the community together to celebrate, support small businesses, and enjoy the city center through a mix of returning favorites and new experiences, all wrapped in winter magic.

WinterLand Kickoff at Public Square

Downtown Cleveland invites everyone to come early, stay late, and indulge in a full day of festive fun. With extended hours and an expanded event lineup on Public Square, immersive activations throughout the core, and a reimagined tree lighting, there’s a holiday moment waiting for everyone!

“This year, WinterLand is designed to let people experience the magic of downtown at their own pace and on their own schedule,” said Michael Deemer, Downtown Cleveland President & CEO. “By extending programming throughout the day and spotlighting our incredible small businesses and cultural gems, we’re making it easier than ever for residents and visitors to take it all in, from holiday lights, live entertainment and decorations to shopping, popup bars, and more.”

New Holiday Magic Awaits

WinterLand 2025 rings in the season with a refreshed format and new additions that are sure to enchant visitors of all ages throughout the day, instead of centering everything around a single evening event.

  • Destination Cleveland’s IlluminateCLE – Beginning at 5:30 p.m. and repeating every 30 minutes until 11 p.m., this dazzling new holiday light show will debut with three original songs by local artists, and the 50-foot tree in Public Square will sparkle with synchronized lights, complementing the half a million additional lights around the Square.

  • Storefront Decorating Contest – For the first time, Downtown Cleveland is launching a contest with local businesses. Stroll through the festive streets and use the “Merry Map” to discover and vote for your favorite holiday display. Businesses interested in participating must submit intent by Oct. 31 to be eligible for a $500 cash prize. Learn more here.

  • Superior Avenue – Instead of closing for a single fireworks show, Superior Avenue will remain open to pedestrians throughout the day, improving access to the expanded event lineup and businesses across downtown. Live music and performances will take place on Public Square’s north lawn stage.

The Classics Return

Ice Skating on Public Square’s Ice Rink

WinterLand’s mainstay festivities begin at 12 p.m. on Public Square, giving visitors plenty of time to explore downtown before the first tree lighting and light show at 5:30 p.m.

  • Public Square Ice Rink – The rink opens for the season and welcomes skaters from 12 p.m. to 10 p.m.

  • Fire Pits, Food Trucks & Festive Tunes – Stay warm and cozy by the fire while enjoying s’mores, hot chocolate, fan favorite food trucks and live music from Apostle Jones, Da Land Brass Band and more.

  • The Grinch – Keep an eye out for the grumpy guy in search of holiday magic and fun photo ops to help his heart grow three sizes.

  • Santa Claus – The jolly guy in the red suit will also make a special appearance on Public Square to greet visitors, snap photos and listen to holiday wishes inside his merry tent.

  • Jingle Bell Tent – Play games, try to win prizes and check out the Book Bank giveaways. Downtown Cleveland partners will also be on the Square to spread holiday cheer, including the GCRTA Holiday Trolley, Destination Cleveland Truck and letters, Cleveland Public Library’s Story Walk, Great Lakes Science Center Activation, Soldiers’ & Sailors’ Patriotic Santa and Lutheran Metropolitan Ministry (LMM).

  • Support for Our Neighbors in Need – Downtown Cleveland is partnering with LMM to host a digital goods drive. Extending through the holiday season, Downtown Cleveland encourages everyone who can, to donate everyday items to help those in supportive services through the following:

• Small Business Saturday – Get a jump start on your holiday shopping and support local merchants throughout downtown.

XMAS Bar in the Flats

Cleveland Bazaar at the 5th Street Arcades

Need help finding all the holiday fun? Stop by the Downtown Cleveland Hospitality Kiosk, located in the southern half of the Square.

A Walkable Holiday Experience

The holiday magic doesn’t stop at Public Square. Head over to activations at 5th Street Arcades, Tower City Center, Cleveland Public Library, Playhouse Square and more, all just steps away. Events include:

Fun All Season Long:

WinterLand is just the beginning. The festive spirit continues downtown all winter long with:

  • Bright Nights on Public Square – Weekends in December

    • Ice Skating, through Feb. 1

    • Cheer Garden serving alcoholic beverages

    • Firepits and s’mores

    • Holiday tunes

  • Snow Days – When there’s enough snow, sled down Mall B, using your own tube or borrow one onsite; follow Downtown Cleveland’s social media for snow day alerts.

  • New Holiday Lighting in Voinovich Park – Featuring a 20-foot-tall tree sparkling against the backdrop of Lake Erie

  • Public Square Lighting – Through February

For the latest WinterLand updates and more about ways to celebrate the season with family-friendly experiences that showcase the diversity and vibrancy of our city, visit https://winterlandcle.com/.

WinterLand is produced in partnership with the City of Cleveland and made possible by K&D Group, Bedrock, Cleveland Public Power, Hughie’s Event Production Services, Circle K, Block by Block, Aerial Agents, Jack Frost, and many more.






Julia Matter
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