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Trip Planner: Winter in The Land

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

Heather Tunstall September 29, 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: Get Cold

Breakfast: Starting Strong in Tremont

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: It's Bigger than Sledding

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. This year it is running Nov. 27 - Feb. 28 at the Chalet in the Cleveland Metroparks Mill Stream Run Reservation (reservations required). Riders must be at least 42 inches tall and gloves or mittens that cover the fingertips are mandatory.

Lunch: Brew Kettle

For a quick lunch, head to The Brew Kettle in Strongsville before continuing south toward Boston Mills & Brandywine. Fuel up with slow-smoked barbecue and comfort food like the Smoked Cheese Steak, Buffalo Chicken Wrap, Smokehouse Pulled Pork or or one of their juicy burgers.

Afternoon: Choose Your Winter Vibe

With tummies full and your toes are warmed up again, it's time to head back outside. Choose your winter vibe: hit the slopes at Boston Mills & Brandywine for skiing or snowboarding or slow it down and get a beautiful winter hike in through Cuyahoga Valley National Park.

If you’re heading to the slopes, Boston Mills/Brandywine offers terrain for beginners and seasoned skiers and snowboarders alike. New to the sport? Lessons and rental equipment make it easier to give it a try. If you prefer both feet on the ground, bundle up and check out the Ledges Trail at Cuyahoga Valley National Park for views of the scenery and gigantic icicles along the way.

Dinner: Warm-up Options in AsiaTown

After a day in the cold, head back just outside of Downtown and warm up in AsiaTown. Grab a steaming bowl of tonkotsu or spicy miso at Alpha Ramen, settle in with pho at #1 Pho or Superior Pho or follow your cravings to one of the neighborhood’s many other restaurants. After a day on the slopes, trails or toboggan chutes, a hot bowl of noodles hits just right.

Evening: See Downtown Shining

End the night under the lights Downtown. Take a stroll to see Illuminate CLE transform some of Cleveland’s most recognizable buildings with colorful light displays in Public Square. If you’re not ready to call it a night, head to East 4th Street for a cocktail. During the holiday season, spots like Society Speakeasy and Foundation Room upstairs at House of Blues lean into the festivities with seasonal drinks and decked-out spaces perfect for one more cozy stop before heading in for the night.

Day 2: Get Cozy

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 Kimpton Schofield Hotel for your morning meal, where you can grab some avocado toast, Sante Fe 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 with SEE CLE to get the inside scoop on Downtown landmarks, buildings, architecture and Cleveland 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: Escape the Cold at KafeLA

It is most likely gray outside. So trade those for a little L.A. sunshine energy at KafeLA in St. Clair Superior. The colorful neighborhood café feels like a mini vacation from Cleveland winter, but the food is reason enough to stop. Owner, Kayla Dial serves up everyhing from shrimp and grits to tropical smoothies to the classic Cleveland polish boy. You are guaranteed to be fully fueled up before heading to University Circle, then reluctantly step back into the cold.

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 for everyone at The Cleveland Museum of Art and free for Ohio residents and visitors 18 and younger at 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.

Need a Warm-Up? Duck into The Coffee House at University Circle for coffee or tea before continuing on to your museum crawl.

Late Afternoon: A Trip to the Tropics

Ready to forget it’s winter for a while? Step inside the Cleveland Botanical Garden for Tropical Holiday, a new seasonal experience filled with lush plants, island-inspired adventures and plenty of festive surprises. Wander through the warm glasshouses, browse the holiday marketplace and soak up a little tropical energy without ever leaving The Land.

Dinner: Keep the Escape Going

End the weekend with Brazilian comfort food at Batuqui on Larchmere Boulevard. Set inside a cozy restored Victorian house, this Greater Buckeye neighborhood staple serves Brazilian favorites in a space that feels especially inviting after a day out in the cold. Settle in, order something warm and toast to a winter weekend well spent in The Land.

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