5 Best Cities to Celebrate the Winter Holidays

While 2020 may have put a dent in some our travel plans, that doesn’t mean we can’t start preparing for next winter – or a safe, socially-distanced getaway this season. Here’s five winter cities you need to visit!

Last month, we showed you the best cities to experience fall this year. Now, we’re highlighting some of the best places to celebrate the winter holidays! The end of the calendar year brings cold weather (sometimes even snow), holiday celebrations and honored-traditions with loved ones. While we may not actually get to visit some of these cities for awhile, we’re already planning our next winter getaway trips for the holidays. Here are some of the best of the best!

Read: 4 Things You Can Do to Protect Your home During Cold Months

Frankenmuth, Michigan

This holiday oasis celebrates Christmas every single day of the year! Frankenmuth is home to the world’s largest Christmas store, Bonner’s Christmas Store, which has over 50,000 holiday decor options and is the size of almost two football fields! Besides being the ultimate Christmas town, Frankenmuth is also known as Michigan’s “Little Bavaria,” and upholds many German traditions all year-long. During the winter holiday season, you can enjoy cozy horse-drawn carriage rides, a downtown Christmas market and even a 5k race just days before Christmas. 

Sun Valley, Idaho

There’s more to do in this quaint city besides skiing! Sun Valley is often a broader term to include the cities surrounding this resort town — from Ketchum, Hailey and Bellevue, the region is the perfect winter wonderland destination with plenty of holiday traditions. There’s multiple December tree lighting ceremonies, holiday markets, live concerts and even a soiree every winter solstice. Each year, the Christmas Eve Torchlight parade is a family-favorite tradition. Skiers make their way down Dollar Mountain, a popular slope for novice skiers, with torches while a fireworks show lights up the sky. We can’t think of anything more magical! And if you miss the Christmas Eve celebration — Dollar Mountain hosts a similar event on New Year’s Eve. Except this time, you get to be the ones skiing down the mountain! 

Stockbridge, Massachusetts

Stockbridge became a dream holiday destination by artist Norman Rockwell. In his hometown, Rockwell painted downtown Stockbridge (the work appropriately called Stockbridge Main Street at Christmas) to capture the spirit of Christmas in small towns across the country. Each year in December, the city recreates his painting as part of their holiday celebrations. Old automobiles are placed in the exact spots in his artwork, roads are closed and families are invited to step into a little piece of New England history. On Main Street, you’ll find holiday marketplaces and light shows, festive home tours and holiday book readings for children at the local library. Stockbridge is part of Berkshire County (known as The Berkshires), and is a quick drive to ski slopes, horseback riding trails and historic inns to give you a true taste of the holiday season. With all the things to do this winter, it’s no wonder Stockbridge is known as the Christmas town of New England!

Leavenworth, Washington

The town of Leavenworth, Washington is no joke for holiday lovers alike. Dawned in Christmas lights, the entire town looks like it came straight out of a Hallmark movie. The historical homes that line the streets of leavenworth feature craftsman styles and gingerbread architecture – fitting, right? Although some of the events for this year have been cancelled, you can still add the small, Bavarian town on your list of places to see this winter. Things like glass blowing and snowshoeing are still available to tourists, as well as wreath making and indigenous language virtual classes.


North Pole, Alaska

With a name like North Pole, it’s impossible to deny this city’s holiday spirit! Take a stroll down festive street names like Santa Claus Lane and Kris Kringle Drive, purchase holiday gifts from the Santa Claus House, attend the two-day tradition, Winterfest, or enter an ice sculpture in the annual North Pole In Ice contest. In this city, every day is a new opportunity to celebrate Christmas! Santa and his reindeer spend time year-round in the Santa Claus House to greet children and take photos. One of the most special traditions in North Pole takes place in the city’s post office. While the city is over 1,700 miles away from the North Pole region we all know and love, the post office receives over 400,000 letters each year addressed to Santa. Of course, Santa’s magic still extends to this city, as community volunteers work to respond to every single letter. How special is that! If your family wants to send a letter to Santa, you can simply address the envelope to “Santa Claus, North Pole, Alaska,” and your letter will find its way to North Pole!

These winter wonderland destinations are the perfect place to start new holiday traditions. Be sure to check local restrictions before making any plans, but if you’re ready to find a home that brings holiday cheer every day of the year — browse through to find your perfect holiday home!

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Andrea is a recent college graduate who loves writing, social media and coffee! She loves covering celebrity home listings, keeping up with the latest style trends and working with the team!

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