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 29 in 2025). 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.
The 2025 celebration is quickly approaching, and the schedule this year looks pretty stacked – AND there’s a brand new attraction coming!
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 2025.
Top things to do/see at WinterLand in 2025
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 29.
1. Outdoor fun at Public Square
WinterLand always centers around Public Square. Some things to do there this year include:
- Ice skating – The Cleveland Foundation Skating Rink will open for the season on Friday, November 28. 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.
- Fire pits – Roast marshmallows and enjoy hot cocoa around cozy firepits.
- Live music – A DJ and various bands will be performing on Public Square from 3 noon on November 29.
- 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.
Also around Public Square and Mall A, you can…
2. Get photos with Santa and the Grinch
There will be photo opportunities with Santa from noon-5 p.m., and photo ops with the Grinch from 2-5 p.m.
The Soldiers’ and Sailors’ Monument will also be offering Patriotic Santa photo ops separately.
3. Get festive at Tower City
Tower City will be bustling all day for WinterLand. A few things you can expect to find (most of which continue through the holiday season) include:
- Holiday character photo ops
- An ice-less “sock skating” rink
- A DJ and dancing
- “Snow” falling around the Christmas tree in Skylight Park
- And more!
You’ll also want to have a chat with Bruce the Spruce (he’ll be chatting with guests from noon-4 p.m. in his special forest environment), and take a ride down the red “Story Slide” that’s a nod to the movie “A Christmas Story.”
Check out more details about holidays at Tower City here.
4. Get holiday shopping done
Cleveland Bazaar will be hosting its annual holiday pop-up market inside the 5th Street Arcades during WinterLand. You’ll be able to shop from local small businesses for unique gifts.
The holiday market will be running from 10 a.m.-7 p.m. on November 29.
Be sure to visit Coco’s Chalky Paints, which now houses a full-on selfie museum!
And, while you’re there, you may as well pop across the street to see the Cleveland Arcade decked out for the holidays, too!
5. Enjoy CPL’s Merry Maker Fest
The Cleveland Public Library’s main branch downtown always hosts events during WinterLand and throughout the holiday season.
This year, you can enjoy workshops throughout the library on November 29 – make things like bath bombs, photo ornaments, and origami bookmarks. You can also visit with reindeer (a family favorite every year!), play arcade games, and more. Find the full event description here.
6. Catch the RTA Holly Jolly Trolley
Keep an eye out for this festive trolley during the WinterLand kickoff; it’ll be decked out inside for photos, and you can visit in the afternoon in Public Square.
7. Have a festive holiday drink
Get into the holiday spirit with some literal holiday spirits!
JACK Casino will once again be running its Sleigh holiday pop-up bar up on the 3rd floor of the casino. The bar will be decked out for Christmas and serving up festive holiday cocktails. It will be open Thursday, Friday, and Saturday nights, and opening on November 26.
Also nearby will be the holiday pop-up bar inside Society Lounge on E. 4th street.
RELATED: Drink Up at These Christmas Pop Up Bars in Cleveland
8. Public Square tree lighting
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 29, and will include music and the unveiling of a brand new lighting/illumination show on Terminal Tower and other buildings around Public Square. The new lighting show (featuring 3 brand new songs and choreographed lights) will repeat every 30 minutes from 5:30-11 p.m.
Note: There will NOT be any fireworks this year. They are being replaced by the new illumination show.
9. See holiday decorations downtown
WinterLand is also a great time to check out the Christmas decorations that go up around downtown. This year, Downtown Cleveland is also running a holiday window decorating contest for downtown storefronts, so hopefully there will be some good ones to see!
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.
When is WinterLand? The kickoff event with the tree lighting always takes place the Saturday after Thanksgiving. In 2025, that’s November 29th.
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. You can also skip the parking and take the RTA train direct to Tower City.
READ NEXT: Christmas in Cleveland: The Best Things to Do This Holiday Season
Who’s planning on going to WinterLand this year?
Amanda was born and raised in northeast Ohio, and has always been a fangirl of her home state. Now, she’s sharing her love of the Cleveland area, highlighting all the best things to do, see, and eat in the CLE. She’s been running Cleveland Traveler since January 2019.
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.
Thanks for pointing that out, Gen! I missed that when I updated for this year. I’ll get it fixed!
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.
Loretta
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.
Let’s talk about parking – in the olden days parking downtown on off hours after 6pm was free. However now with the new electronic parking meters it like they are changing for downtown parking 24hrs a day. With variable pricing during events. Any information if City of Clevo will be increasing parking rates for this event? I live 7mins from downtown, but I still find these new parking fees a discouragement to going Downtown to dine and events.
That’s a good question, and I’m not sure of the answer! The electronic parking meters are new; I doubt they will be increasing prices on those for any events, but the downtown garages could charge “special event” prices.
Is there horse drawn carriages to take you around Public Square to see Christmas Lights?
Not this year, no.