ULTIMATE Guide to the Downtown Cleveland WinterLand Festival

If you’re anxiously awaiting the arrival of the holidays and you can’t wait to get into the holiday spirit, the Cleveland WinterLand festival is the perfect place to do it.

Held in late November in Cleveland Public Square, this event is packed full of fun and holiday cheer. Bring your friends and family for a whole host of activities that are sure to bring a smile to your face. If you’re planning to attend Cleveland’s WinterLand, here’s everything you need to know.

Getting to Know Cleveland’s WinterLand

Formerly known as WinterFest, this event is one of the largest holiday attractions in Northeast Ohio and is an important holiday tradition for thousands of Ohioans. Clevelanders especially love Christmas, and the WinterLand festival is one of the biggest and best ways to kick off the holiday season.

For more than 30 years, the free event has taken over downtown Cleveland for a whole day of celebration and fun. An entire day of holiday fun ends with the lighting of the big Christmas tree in Cleveland Public Square and a fireworks show.

12 Things to Do During the Cleveland WinterLand Festival

With so many fun events going on during WinterLand Cleveland, you might wonder where to start the fun. No matter where you start, you’re guaranteed to have a good time.

Soak in the Festivities in the Public Square

Much of the fun during WinterLand centers around the Public Square, and it’s the place to be during this magical event.

Ice Skating

Lace up a pair of skates, and hit the Cleveland Foundation Skating Rink for some leisurely ice skating. Skating runs not only during the festival but also through mid-February, and you can rent a pair of skates while you’re there.

Food Trucks

After you’re done skating, visit one of the local food trucks around the square. These trucks offer a variety of delicious eats, and you can even buy adult beverages at a few of them.

Holiday Characters & Marshmallow Roasting

While you’re hanging out in the Public Square, keep your eyes peeled for some of your favorite holiday characters. You can warm up around one of several fire pits while you’re roasting some marshmallows too.

Lights & Decorations

Of course, what’s a holiday celebration without lights and decorations? Once the tree is lit at night before thousands of spectators, the Public Square comes alive with color thanks to magnificent displays that include an illuminated Terminal Tower.

Have More Holiday Fun at Tower City Center

Tower City is a great spot to get into the holiday spirit if you plan on attending the Cleveland WinterLand festival. If you’re looking for gifts for friends and family, visit Tower City’s Christmas Baazar Holiday Market. Kiddos will love different stations, like face painting, crafting, and balloon twisters.

When you’re ready for a break, warm up with some yummy hot chocolate and cookies. There are even moving screenings (with popcorn, of course!), carolers, and so much more.

Marvel at Kringle’s Inventionasium Experience

While you’re having fun in Tower City, check out Kringle’s Inventionasium Experience. For the youngsters in attendance, this private visit with Mr. Kringle offers a chance to visit his secret workshop and create toys. This memorable experience is sure to leave a smile on their faces.

Chat It Up With Bruce the Spruce

Did we mention that the Cleveland WinterLand festival has it all? It even has a talking Christmas tree!

Stop by Tower Court during the festivities to chat with Bruce the Spruce, a talking tree that’s been a part of Christmas for Clevelanders since the 1960s. After you’ve yakked it up with Bruce, head to Skylight Park for some great photos with a 35-foot tree.

Get Your Photo Taken With Santa

No holiday festival is complete without getting a chance to see the Big Man in Red. If you’re looking to get your photo taken with Santa, you’re in luck because he’ll be at the Soldiers and Sailors Monument in the Public Square.

Additionally, Santa will be historically accurate. In the early 1860s, Harper’s Weekly illustrator Thomas Nast created the American version of Santa that we all know and love. Visitors can take photos with him on their own devices from 11 a.m. to 6 p.m. during WinterLand.

Meet and Greet a Reindeer

If you thought meeting Santa during the Cleveland WinterLand festival was awesome, it gets even better. Make your way to the Eastman Reading Garden on Rockwell Ave to see a real, honest-to-goodness live reindeer that will make the perfect photo on your social media.

Have Some Fun at the Cleveland Public Library

If you’re anxious for the tree-lightning ceremony to start, kill some time at the Cleveland Public Library for a whole host of activities. Visitors can enjoy free music, family activities, and so much more. This is the perfect place to have fun before you head to the Public Square.

Get Down at the Turkey Jam

After you’ve spent a fun-filled day bopping around downtown Cleveland, head to the KeyBank State Theatre to get your groove on. If you love R&B hits, get down with Bobby Brown, Ruff Endz, Ginuwine, and SWV. It’s the perfect end to the perfect day!

Shoot Some Hoops With the Cleveland Cavaliers

WinterLand Cleveland brings everyone downtown, including the Cleveland Cavaliers of the National Basketball Association.

Join in the fun with the Cavs’ #AllForFunTour, a four-wheeled fan-favorite destination where visitors can enjoy interactive NBA 2K gaming, shooting some hoops, a memorabilia wall, and so much more.

Enjoy Christmas Carolers at Caroler’s Square

What’s a holiday celebration without a little bit of music? If you’re looking to hear some Christmas music during the Cleveland WinterLand festival, head to Brett Hall to enjoy a live performance of all the holiday favorites from the Cleveland Opera Theater.

While you’re at Brett Hall, grab a free craft kit to take home. This craft will look perfect among your home holiday decorations.

Relax With a Refreshing Holiday Drink

If you’re looking for a drink to warm up during the WinterLand festivities, there are plenty of spots where you can enjoy steaming hot cocoa and other refreshments. But if you’re looking for adult drinks, there are several spots you can go for some holiday spirits.

• The X-Mas Bar is the newest pop-up bar in Cleveland. It offers an unforgettable holiday experience with music, drinks, great views, and tasty food at Flats East Bank.
• Holiday Spirits – Poured by Nuevo in Tower City offers visitors both alcoholic and nonalcoholic beverages and plenty of holiday cheer with decorations, tinsel, and lots of lights.
• The JACK Sleigh Holiday Pop-Up Bar in the JACK Cleveland Casino returns for the season, beginning with WinterLand, and features plenty of sweet treats and themed cocktails.

Hop Aboard the Holiday Trolley

There’s a lot to explore during the Cleveland WinterLand holiday events, but if you’re looking to take a breather, hop aboard the holiday trolley. The Greater Cleveland Regional Transit Authority will offer holiday trolley services from mid-afternoon through the evening, so climb aboard.

FAQs About the Cleveland WinterLand Festival

Make Plans To Attend Cleveland’s WinterLand!

Cleveland’s annual WinterLand festival has been a holiday tradition for Clevelanders for a reason: It’s bursting with awesome activities and holiday atmosphere, and it makes for the perfect holiday season kickoff.

This is the perfect holiday event for the entire family. Whether you want to check out the Cleveland Bazaar for holiday shopping, stroll by dazzling light displays, enjoy a warm cup of hot cocoa and cookies, or even go ice skating, you can do it all and then some.

So make plans to attend the Cleveland WinterLand festival this holiday season. No matter how cold it may be, the plethora of activities and the festive atmosphere will be more than enough to warm you up while you have a good time.

Looking for more things to do around Cleveland? Check out the Greater Cleveland Aquarium and numerous museum exhibits or even plan a day trip from Cleveland.