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Cleveland Winterfest 2021: 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 Winterfest.

This free downtown-wide event takes place each year the Saturday after Thanksgiving (November 27 in 2021). There’s a whole day of special things to see and do in downtown Cleveland, culminating in the lighting of a giant Christmas tree on Public Square after dark.

After being a virtual event sans tree in 2020, Winterfest is back in-person for 2021. And the schedule this year looks pretty amazing!

Public Square Christmas lights
WInterfest 2019

There are special holiday-themed things to do all through downtown Cleveland throughout the day for Winterfest, from special shopping pop-ups to ice skating to carriage rides and much, much more.

Read on to learn about all the things to do and see at Winterfest in 2021.

Top things to do/see at Winterfest in 2021

1. Outdoor fun at Public Square

Public Square ice rink
Ice skating during Winterfest

Winterfest 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 during Winterfest. Skating is $12 per person, which includes skate rentals. The rink will be open from noon-10 p.m. during Winterfest.
  • Carriage rides – Horse-drawn carriage rides are always popular during this event; they are usually free, but must be booked in advance. (And I’m sorry to say they’re already completely sold out for 2021!)
  • Carolers – Stop by the Old Stone Church to listen to carolers and enjoy cookies.
  • Food trucks – There will be local food trucks around from noon-8 p.m.
  • 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

2. Holiday spirit at the Cleveland Library

There will be family-friendly things to do at the Cleveland Main Library throughout the day on November 27. Some of the highlights include:

  • See live reindeer (noon-3 p.m. in the Eastman Reading Garden)
  • Watch ice sculpting (2-4 p.m. in the Eastman Reading Garden)
  • See the Toy Soldier perform (from 5-5:30 p.m. and 6-6:30 p.m. in the Louis Stokes Wing Auditorium)

There will also be crafts, and some special visitors throughout the day at the library.

3. Enjoy the family fun zone

Walk down to US Bank Plaza a few blocks down from Public Square to enjoy Slick Woody’s Family Fun Zone. Here, outdoor games like cornhole will be set up to play.

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 inside the Halle Building downtown from noon-6 p.m. – and you might just get lucky enough to receive your very own magic key from him!

5. Get holiday shopping done

5th Street Arcades in Cleveland
5th Street Arcades

Over at the 5th Street Arcades, Cleveland Bazaar will be hosting one of its holiday pop-up markets to coincide with Winterfest. Shop 45 local artisans and businesses for unique gifts.

The holiday market will be running from 10 a.m.-8 p.m. on November 27.

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

6. Make s’mores around a fire

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

Head over to the Key Tower pavilion on Mall A to warm up around fire pits while sipping hot cocoa or maybe an adult beverage from the cash bar (opening at 3 p.m.).

JACK Entertainment will have s’mores kits available from 4-8 p.m., too, which you can make together around a fire.

7. Catch the RTA Holly Jolly Trolley

RTA Holly Jolly Trolley at Winterfest

Keep an eye out for this festive trolley during Winterfest; it’ll be decked out inside for photos, and you can even get a photo with Santa here!

8. 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 is set for 6-7 p.m., and will include music and fireworks afterwards.

(I’ve read reports that the tree lighting is at 6 p.m., and others that say it’s at 7 p.m. The ceremony is usually a pretty drawn-out affair, so my guess is it’ll start a little after 6, and the fireworks might start around 7. If you’re planning to go, I would have your spot to watch picked out by 6 p.m. just to be safe.)

9. Have a festive holiday drink

JACK Casino is opening an exclusive holiday pop-up bar this year called Sleigh. It’ll be decked out for Christmas and serving up festive holiday cocktails. The bar will be open from 6 p.m.-2 a.m. for Winterfest.

10. See holiday decorations

Jack Casino Christmas decorations
Higbee’s windows at JACK Casino

Winterfest 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, a tree and decorations inside Tower City at Terminal Tower, plus plenty more decorations around downtown.

If you make it down to Playhouse Square, you can also check out the Festival of Trees at the Allen Theatre, and the giant walk-through Christmas bulb on US Bank Plaza.

Playhouse Square Christmas bulb

Winterfest FAQ

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

What is Winterfest? 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.

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

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

Where can I park for Winterfest? 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 Winterfest this year?

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