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Cleveland WinterLand 2022: How to Enjoy the City’s Holiday Kickoff Event

Clevelanders LOVE Christmas, and the holiday season officially kicks off in the city each year at the first day of WinterLand.

Previously known as Winterfest, this free downtown-wide event begins each year the Saturday after Thanksgiving (November 26 in 2022). There’s a whole day of special things to see and do in downtown Cleveland, culminating in the lighting of a giant Christmas tree (and fireworks) on Public Square after dark.

The 2022 celebration is quickly approaching, and the schedule this year looks pretty amazing!

Public Square Christmas lights
WInterfest 2019

There are special holiday-themed things to do all around downtown Cleveland throughout the day for the WinterLand kickoff, from special shopping pop-ups to ice skating to marshmallow roasting and much, much more.

Read on to learn about all the things to do and see at WinterLand in 2022.

Top things to do/see at WinterLand in 2022

Note: Downtown Cleveland wants to make WinterLand a season-long celebration, with events and activations happening all throughout the winter. This post, however, will focus specifically on everything you can do downtown during the event kickoff on November 26.

1. Outdoor fun at Public Square

Public Square ice rink
Ice skating in Public Square

Winterfest/WinterLand always centers around Public Square. Some things to do there this year include:

  • Ice skating – The Cleveland Foundation Skating Rink is back this year, opening for the season on November 25th (and running through February 20, 2023). Skating will be available during the WinterLand kickoff, and prices include skate rental.
  • Food trucks – There will be local food trucks around throughout the afternoon, and some places where you can purchase adult beverages.
  • Holiday lights and decorations – Definitely stick around after the tree lighting to enjoy the light displays. There are lights all around Public Square, and Terminal Tower will also be illuminated.
Public Square holiday lights
Terminal Tower through holiday lights

Also around Public Square and Mall A, you can…

2. Make s’mores around a fire

Like last year, there will be fire pits throughout Public Square and Mall A for you to warm up around throughout WinterLand.

In 2021, JACK Entertainment provided s’mores kits, and hopefully they’ll be back this year, too!

Making s'mores at Public Square
Making s’mores at Public Square

3. Get photos with Santa

The Soldiers’ and Sailors’ Monument is presenting “Patriotic Santa,” and you can take photos for free from 11 a.m.-6 p.m. during WinterLand.

4. Say hi to Mr. Jingaling

If you grew up in Cleveland, then you’ll know who Mr. Jingaling is! (And if you didn’t grow up in Cleveland, all you need to know is that Mr. Jingaling is Santa’s top elf, and the keeper of the keys to Santa’s workshop.)

Mr. Jingaling will be appearing in Public Square from 6-9 p.m. (after the tree lighting) – and you might just get lucky enough to receive your very own magic key from him!

5. Get festive at Tower City

Tower City at Christmas
Decorations inside Tower City

Tower City’s new Skylight Park will be bustling all day for WinterLand, from 10 a.m.-7 p.m. A few things you can expect to find include:

  • A Holiday Market in conjunction with Cleveland Bazaar, where you can shop and support local makers on Small Business Saturday
  • Screenings of classic Christmas movies with popcorn
  • Hot cocoa and cookies to enjoy
  • Arts and crafts projects
  • Carolers
  • A kid’s train in Station Court
  • And more!

6. Holiday spirit at the Cleveland Library

There will be family-friendly things to do at the Cleveland Main Library throughout the day on November 26. Some of the highlights include:

  • See live reindeer (noon-3 p.m. in the Eastman Reading Garden)
  • Listen to holiday carols performed by the Cleveland Opera Theater (3-4 p.m. at Brett Hall inside the library)

There will also be family-friendly activities throughout the day at the library from noon-4 p.m. You can also pick up a free seasonal craft kit from Brett Hall (while supplies last).

7. Get holiday shopping done

5th Street Arcades in Cleveland
5th Street Arcades

Along with the market inside Tower City, Cleveland Bazaar will ALSO be hosting another holiday pop-up market inside the 5th Street Arcades. You’ll be able to shop even more local small businesses for unique gifts.

The holiday market will be running from 10 a.m.-7 p.m. on November 26.

Be sure to visit Coco’s Chalky Paints, which last year transformed its storefront into an immersive Narnia experience.

And, while you’re there, you may as well pop across the street to see the Cleveland Arcade decked out for the holidays, too!

8. Catch the RTA Holly Jolly Trolley

RTA Holly Jolly Trolley at Winterfest

Keep an eye out for this festive trolley during the WinterLand kickoff; it’ll be decked out inside for photos, and you can visit from 3-7 p.m. on November 26!

(Last year it was parked up in Public Square.)

9. Have a festive holiday drink

This year there will be TWO holiday pop-up bars inside Tower City.

The first is Sleigh at JACK Casino, which is up on the 3rd floor. The bar will be decked out for Christmas and serving up festive holiday cocktails. It will be open Friday and Saturday nights from Nov. 25-Dec. 17 (including the night of WinterLand).

The second is a new bar for this year, called Holiday Spirits: Poured by Nuevo. It will be located inside The Eatery in Tower City, and will be serving up festive alcoholic and non-alcoholic drinks.

Also nearby will be the Miracle holiday pop-up bar inside Society Lounge on E. 4th street.

RELATED: Drink Up at These Christmas Pop Up Bars in Cleveland

10. Public Square tree lighting

Winterfest fireworks
Tree lighting and fireworks in 2019
Winterfest tree lighting in 2021
Tree lighting and fireworks in 2021

The big event of the night will be the lighting of the tree and all the other lights around Public Square. The lighting ceremony is set to start at 5:30 p.m. on November 26, and will include music and fireworks afterwards (fireworks are supposed to start at 6 p.m.).

The lighting ceremony will include live music and an appearance by Santa.

This event is always really popular, so I do recommend claiming a spot to watch before 5:30.

11. See holiday decorations downtown

Jack Casino Christmas decorations
Higbee’s windows at JACK Casino in 2019

WinterLand is also a great time to check out the Christmas decorations that go up around downtown. You can see the Higbee’s-inspired holiday windows at JACK Casino and inside Tower City (this year they may just be inside Tower City), plus plenty more decorations around downtown.

Winterfest/WinterLand FAQ

Have questions about WinterLand? We’ll try to answer them for you.

What is WinterLand? It’s Cleveland’s main holiday event, culminating in the lighting of the city’s Christmas tree. It’s put on by the Downtown Cleveland Alliance, and used to be called Winterfest (the name changed in 2022).

Where is WinterLand? The activities center around Public Square, but there are festive things happening all around the downtown area.

How much is WinterLand? The event is free for the public.

Where can I park for WinterLand? If you’re planning to come downtown for the tree lighting, why not make a day out of it? If you arrive downtown early, you should have no problem finding parking in any of the downtown surface lots or garages.

READ NEXT: Christmas in Cleveland: The Best Things to Do This Holiday Season

Who’s planning on going to WinterLand this year?

This Post Has 4 Comments

  1. Gen

    Great review of the Winterland activities. HOWEVER, one point I’m confused about. You list the Christmas Tree display at the Allen Theater as being something to be seen if you make it down to the theater area….and it has been set-up in the past during Winterfest. This year, their website definitely states that the dates for the Christmas tree display are 12/3 through 12/22, so it will not be set-up during Winterland. If someone makes the trek all the way there from public square, they’ll definitely be disappointed to find out it hasn’t started yet.

    1. Amanda

      Thanks for pointing that out, Gen! I missed that when I updated for this year. I’ll get it fixed!

  2. Loretta Tenkku

    I cannot find anywhere on the internet how to reserve and advance pay for a horse carriage ride on the day of all of these Winterland 2022 events (Nov. 26). Can u direct me as to who I need to contact to reserve a carriage ride ?
    Thank you in advance.

    1. Amanda

      Hi Loretta! I haven’t seen any mention of carriage rides happening this year (if I left in a mention of them in the post, I do apologize – I thought I removed them!). In years past, I think they were either first-come, first-served, or you could book online. But the official WinterLand website doesn’t mention carriage rides for 2022.

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