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Trip Planner: Winter in The Land

Cabin fever? Here’s two days of inspiration for Cleveland winter adventures.

Heather Tunstall January 07, 2026

In Cleveland, the winter requires some extra creativity to make leaving the lure of your warm and cozy home worthwhile. Winter can be brutal here on the north coast, but you can make the most of it by getting fully immersed in arts and culture, tipping back some warm drinks and maybe building a snowman or two.

You've never had this much fun with so little mercury in the thermometer. Bundle up, because it’s time to make The Land your winter playground.

Day 1

Breakfast

Start your morning in Tremont fueling up at one of the coziest coffee shops in the city, Roasted Tremont. Roasted is a Cleveland staple and serves all different season-specific lattes, teas and a hot chocolate that will have you feeling all kinds of boujee. It's topped with marshmallow fluff that's torched to gooey golden goodness right in front of you. It's the only right way to start your winter adventure.

Morning

Sledding on a tiny plastic shield down a steep hill not really your thing? Let us recommend something exponentially better: tobogganing. We’re talking legit tobogganing down a bona fide toboggan chute. To be clear, that’s a 700-foot tobogganing chute that’ll have you going down at speeds of up to 50 miles per hour. The adrenaline rush alone will surely warm you up. It happens throughout the winter at the Chalet in the Cleveland Metroparks Mill Stream Run Reservation.

Lunch

For a quick lunch, head to The Brew Kettle before you drive down to the Cuyahoga Valley National Park, about 20 miles south of Downtown. Warm up with comfort food off of their enormous menu, featuring convenient hand-helds like Buffalo Chicken Wraps, Smoked Cheese Steaks or one of their famous burgers.

Afternoon

Get your second dose of adrenaline at Boston Mills & Brandywine where you can ski, snowboard and snow tube on 18 trails. The two next-door resorts in the Cuyahoga Valley National Park feature lifts, rental equipment and lodges to warm your toes. Or, if you’re over the downhill rush, opt for the 125+ miles of nearby hiking trails for a crisp stroll through some of Ohio’s most dramatic scenery.

Dinner

After a day full of running around in the great outdoor it's time to get grounded with some comfort food. Pack up the car, crank the heat and head back to The Land where the food that feels like a warm hug will meet you in Ohio City. Mason's Creamery is the holy grail situation for families. Hot ramen to warm you up and give you a much needed nutrient refill and ice cream to to put a smile on everyone's face.

Evening

Head back across the bridge to Downtown to take a stroll along North Coast Harbor before closing out your day. If you still have energy to explore, stop by the mindbending Museum of Illusions, where you can defy gravity in the Reversed Room, hang from a skyscraper, explore interactive exhibits like the Walk-in Kaleidoscope and Vortex Tunnel.

Day 2

Breakfast

Winter in Cleveland isn’t too bad when you’ve got a delicious, hot breakfast with a snowglobe-esque backdrop right downtown. Head to Betts on East 9th at the Schofield for your morning meal, where you can grab some avocado toast, an AM Power Bowl or eggs just about any way you want them. Grab-and-go at this establishment is quick, easy and available for any item on their food menu.

Morning

Want to know why we have the prettiest grocery store ever? Or where you can find the world’s largest outdoor chandelier? Take a personalized tour from SEE CLE, during which you’ll get the inside scoop on Cleveland’s most famous buildings, residents and history from a knowledgeable, engaging guide. Pack your walking shoes – the tour is two hours long, but you’ll have plenty of opportunities along the way to sit and hear the tales of the town.

Lunch

Yours Truly sits in the heart of Downtown just steps from Playhouse Square in the historic Halle Building. You’ve got your choice of homestyle entrees, wraps, sandwiches, soups, salads, or burgers on their extensive menu – and don’t forget the sweet stuff. (We suggest a home baked apple pie for the real deal.)

Afternoon

Drive about 15 minutes east to spend some time in University Circle. This neighborhood is dripping with places perfect for learning about culture, history and art. Experience it all for free at The Cleveland Museum of Art and the Musuem of Contemporary Art. After your mind is full of new ideas and perspective, talk it over on the short walk to the Coffee House where you can indulge in something hot caffeinated beverage and a pastry, all made fresh. 

Late Afternoon

Need a little vacation from reality? Walk 5 minutes over to the Cleveland Botanical Garden where you can spend some time walking the grounds, birdwatching and getting in your steps while surrounded by beauty and warmth. As twilight nears, take a twinkle treelight walk on select woodland paths. A backyard forest getaway right in the city. 

Dinner

Treat yourself to one of the top restaurants in Cleveland, L’Albatros Brasserie and Bar. This upscale hot spot is located in an old carriage house on the campus of Case Western Reserve University. Gorgeous plates of French cuisine are served in a romantic setting or available for curbside pickup. If you're looking for a more casual vibe the Jolly Scholar is the spot for experimenting with their original brews and classic pub food for the whole crew. 

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