5 Awesome Cities That You Should Visit in the Winter!

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Sometimes the best way to get through the winter is to simply embrace it. Enjoy all the fun that the snowy season offers by visiting one of these cities where you can find plenty to do indoors – and even outside!

Montréal, QC

Montréal definitely knows how to make the most of winter! The city looks beautiful under a blanket of snow, in particular the neighborhood of Old Montréal, which is home to the fantastic Old Port ice skating rink in Bonsecours Basin.

Even in winter, you can make your way to the top of Mont-Royal park along the paths and stairways. When you reach the top, you will find another ice skating rink at Beaver Lake, as well as a panoramic view of the city from a lookout spot.

Montréal is also the place to find perhaps the best winter food of all, poutine! The filling combo of french fries, cheese curds, and gravy will definitely warm you up. Try it with a whole smorgasbord of toppings at the uber-popular La Banquise, or stop by Montréal Poutine for the classic dish if you’re in Old Montréal.

Montréal also celebrates winter with a couple of excellent festivals. Igloofest is an EDM dance party in Old Port from Jan 17-Feb 2, 2019 and Montréal en Lumiére lights up the darkest days of winter with a sparkly display in the Quartiers des Spectacles, along with lots of delicious food and wine tasting, from Feb 21-March 3, 2019.

How to get to Montréal: Book a ticket to Montréal from New York City, Boston and beyond!

Chicago, IL

The Windy City also thrives as a snowy city! Sure, everyone seems to talk about how great Chicago summers are, but winters are lots of fun, too!

From The Field Museum to the Museum of Science and Industry to the acclaimed Art Institute, you can appreciate Chicago in the winter by taking shelter in one of its many museums. The Field Museum features the skeleton of SUE the T. rex and much more natural history, while the Museum of Science and Industry lets you do everything from explore an old submarine to watch baby chicks hatch, and the Art Institute of Chicago showcases a wide-ranging collection of Impressionist and Post-Impressionist art.

Chicago is also home to an ever-growing and evolving craft beer scene, so you can cozy up for a pint or a flight at one of the many local breweries. Half Acre has a separate tap room and brewery, so you have plenty of space to hang out inside and taste all their creations, or try out a younger brewery like Cruz Blanca or Grand Central BrewingAndersonville’s Hop Leaf and Bucktown’s Map Room also remain among the most vaunted beer bars in the country.

If beer’s not your thing, don’t worry, Chicago is also home to excellent cocktail bars where it’s easy to while away a winter evening. Try Watershed (hidden in the basement of Pops for Champagne) for Midwestern coziness and locally-soured cocktails, Three Dots & a Dash or Lost Lake for refined tiki drinks, or The Aviary for a one-of-a-kind drinking experience.

How to get to Chicago: Book a ticket to Chicago from Milwaukee, Indianapolis, Grand Rapids and many more locations in the Midwest and across the country!

Boston, MA

Boston was hit by a brutal winter last year, but that doesn’t mean it’s not beautiful in the snow. The historical architecture certainly looks lovely under a blanket of white!

To appreciate architecture indoors, visit the Central Branch of the Boston Public Library. From the carved lions to the intricate murals, you can wander through the library for hours to take it all in. And though the courtyard might not be where you want to spend time in winter, you can stay for awhile in beautiful Bates Hall, which looks just like a library should.

You might not be able to swim in the ocean in the winter, but you can meet all its inhabitants with a trip to the New England Aquarium. See all sorts of sea creatures – jellyfish and turtles and seadragons, oh my! – and don’t miss the adorable penguins!

If you want to warm up your winter with a sweet treat, stop at Max Brenner Chocolate Bar for a decadent chocolate experience. Choose from a menu featuring Italian thick hot chocolate, Mexican spicy hot chocolate, Swiss whipped hot chocolate and more. Each is served in a specially designed “hug mug” to envelope your senses with chocolate coziness.

How to get to Boston: Book a ticket to Boston from New York City, Philadelphia, Washington, D.C. and lots of other locations!

Minneapolis, MN

Minnesotans know how to survive – and thrive! – in winter, so Minneapolis is full of ways to have fun when it’s freezing!

A smart move in a city this cold is to bring the ice rink indoors, but keep the view outside. The floor to ceiling windows at The Depot Rink let you see the city skyline while you skate, but keep you warm at the same time.

You can also hide from the icy chill inside Mia, the Minneapolis Institute of Art. The museum has a wide-ranging collection, including artifacts and masterpieces from artists around the world. And admission is always free!

If you need some food to fortify you against the winter weather, the famous Juicy Lucy – or is that Jucy Lucy? – is sure to be just the thing. Two different restaurants claim to be the creator (hence the alternate spellings) of this cheeseburger where the cheese is actually melted inside the burger patty instead of on top. Make your way to the 5-8 Club for the Juicy Lucy or to Matt’s Bar for the Jucy Lucy to decide which is the best – or just to devour both of them!

How to get to Minneapolis: Book a ticket to Minneapolis from Milwaukee, Madison, Chicago and other places, too!

Toronto, ON

Another city that provides plenty to do during winter is in Canada, of course, so take a trip to the Great White North and explore Toronto!

Visit the Royal Ontario Museum to hide from the wintry weather while exploring everything from history to art. Check out ancient Chinese architecture, see dinosaur fossils, and even walk through a simulated bat cave!

For outdoor fun, bundle up and hit the ice at the rink at Nathan Phillips Square. Located right downtown, this rink is a spectacular place to skate when it is lit up at night and Old City Hall is standing tall as a backdrop.

If you can brave the cold, you’ll definitely want to take a Culinary Adventure Co. food tour, and don’t worry, there will be plenty of stops for you to get your fill of warmth – and excellent food! Go on a tour of one of Toronto’s many foodie neighborhoods, or even head out of the city for an ice fishing or dog-sledding adventure, complete with a chef-prepared lunch or picnic.

How to get to Toronto: Book a ticket to Toronto from New York City, Buffalo, Philadelphia, and many more places!

If you love the cold or cozying up inside, visit one of these cities by booking a ticket on Wanderu or downloading the Wanderu app! And if you’d rather be somewhere warm, we’ll show you the best cities to escape winter next week!

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About the author
Kate Sedrowski

Kate Sedrowski

Kate Sedrowski is on a mission to spread delight while inspiring and encouraging people to travel. Her favorite travel companion is her teddy bear, and her favorite souvenir is the scar from the broken nose she got in a snowball fight in Québec City.
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