Looking for the best winter vacation ideas in the Midwest? From cross-country ski vacations to cozy small towns, here are the best places to visit in the Midwest in the winter:

18 Midwest Winter Vacation Ideas:

Travel in the midwest doesn’t have to stop when the snow starts! Here are the best Midwest Winter vacation ideas:

why me? Hi there! I’m Maddy. I was born and raised in Michigan and grew up on summers on the Great Lakes. Today, I work as a freelance writer and outdoors guide, and have been lucky to have adventured some incredible places throughout the Midwest. Anyways, this article was written by me, a person who has lived in and cares about these places very much, not a computer program!

Note: This article contains affiliate links! This means if you make a purchase based on my recommendation, I make a small kickback at no additional cost to you.

What to pack for a Midwest Winter Vacation:

Winters in the Midwest can be very cold! Make sure you pack for the weather. You’ll want…

• Wool baselayers: after several years of winter hiking in the Midwest and working as a Lake Superior/Pacific Ocean overnight sea kayaking guide I’ve found Smartwool makes some of the best baselayers in terms of warmth and longevity. Check out a guide to women’s baselayers here.
• Fleece mid layers: fleece works as an excellent midlayer for winter hiking, skiing, or any winter activity! You can find excellent fleeces at most thrift stores.
• Cute sweaters: I love to wear fun wool sweaters when exploring in the winter. I make some of my own sweaters (click here for available pieces), or Dale of Norway makes incredible quality beautiful sweaters as well.
• Flexible pants: I wear a pair of Fjallraven Keb Trousers as an outer layer for winter hiking and most outdoor winter activities.
• Warm puffy jackets: having a warm jacket for winter travel in the Midwest is a must! I have Patagonia’s DAS jacket for extra cold trips or trips where I will not be as active. For hiking or more middle of the road cold trips (above zero), I have a Helly Hansen thinner puffy.
• Winter Hiking Boots: I’m honestly still looking for the perfect winter hiking boot. I have a pair of Oboz Sapphire Insulated, and they’re pretty good, but I’m not in love with them the way that my hiking boots can do no wrong. I’ve also had Danner winter hikers, and they were also just okay.
• Spikes to hike in: For most trails that see lots of traffic, you wont need snowshoes, invest in microspikes instead! Trails are more likely to be packed snow and ice from foot traffic than feet of fresh powder.
• Snowshoes: if you do plan on breaking trail, try out some Crescent Moon snowshoes.
• Mittens: I like to make my own wool, Norwegian- inspired mittens! Check here for availability.

1) Sisu & Loyly Sauna & Cross Country Ski

Looking for the coziest Midwest winter vacation? Head up to snowy Grand Marais, Minnesota for a cross country ski and sauna trip. 

Ski the beautiful Pincushion Mountain Trails overlooking the beautiful small town below, then after be sure to hit the beautiful Sisu and Loyly Sauna on Lake Superior. Remember to pick up your Great Minnesota Ski Pass.

2) Snowshoe the Sleeping Bear Dunes

For a cozy and unique winter vacation destination, head to the Sleeping Bear Dunes National Lakeshore. 

Tackle the legendary Dune Climb hike with snowshoes. Known in the summer as one of the most difficult hikes in Michigan for the heat and difficult terrain over loose sand, snowshoeing the Dune Climb is comparatively a cake walk. 

You’re likely to have this adventure mostly to yourself, and will be rewarded with sweeping views of the dunes and Lake Michigan below. Alternately, snowshoe or ski the Pierce-Stocking Scenic Drive for a longer and more difficult adventure. After your adventuring, head to Joe’s Friendly Tavern for a warm up. 

Note: the popular Empire Bluffs trail is not plowed or easily accessible in the winter. Do not attempt to reach.

Looking to explore Michigan this winter? Check out the best winter adventures in Michigan!

3) Visit the Pictured Rocks Ice Climbing Festival

Head out to the Michigan Ice Fest to take an ice climbing class ranging from beginner, to master located in the Pictured Rocks backcountry. Alternately, take a guided ice climbing tour. 

Stay in Munising, Michigan, and enjoy the local breweries and cross country ski trails when you’re not climbing. Not interested in climbing, but want to learn more about it? Attend one of the guest speaker presentations. 

New to winter hiking? Check out this guide to what to wear, how to layer, and how to find winter hiking near you.

4) Visit Bayfield, WI

Known for it’s incredible ice caves that are only accessible in the coldest winters, Bayfield, WI is one of the most magical winter destinations in the Midwest.

What visiting the apostle islands in the summer can look like!

While hiking to the ice caves has not been possible in the National Park in recent years, there is still plenty to do in Bayfield! Cozy up at the Rittenhouse Inn, and hike above the Myers Beach sea caves on the Lakeshore Trail. Grab a bite to eat at Mannypenny Bistro, and remember to keep your eyes peeled for the Northern Lights. 

Check out the best things to do in Bayfield in the Winter

5) Hit the town in Duluth, Minnesota

One of the best places to visit in the Midwest in the winter is the city of Duluth Minnesota. Check out the Bentleyville Christmas lights, or visit the Gleensheen Mansion. For nearby cross country skiing, check out the beautiful Lester Park trails. 

Check out the 16 Best Hiking Trails near Duluth, Minnesota

6) Watch Dogsled Races on the Gunflint Trail

Looking for one of the most adventurous winter destinations in the Midwest? Look no further than Minnesota’s Gunflint Trail. This road stretches deep into the adjacent Boundary Waters Canoe Area Wilderness, and is the perfect place for a winter adventure!

Stay at the beautiful Gunflint Lodge, with views of Canada across the lake and occasional Northern Lights displays. Head to the unique Poplar Haus for some of the most delicious food in the Midwest. Be sure to time your visit with the Gunflint Mail Run and spectate at one of the most fun dogsled races in the North!

The Gunflint Trail is plowed in the winter, but drive with care; cell service may be unreliable. 

Wondering where you can book your own dogsled tour? Check out Points Unknown in Hovland, Minnesota!

7) Skiing and Brews in Bellaire, Michigan

Love craft drinks, skiing, and snow? Head to Bellaire, Michigan for one of the best Midwest winter destinations for skiing & craft beer. The Bellaire area sees one of the highest snowfall totals in Lower Michigan, making it the perfect place to spend a winter vacation!

Stay at one of the nearby ski resorts like Shanty Creek or Boyne Mountain, then spend your evenings in downtown Bellaire visiting Short’s Brewery, one of Michigan’s finest! Not a beer drinker? No worries! Tiny downtown Bellaire also has a wine bar, cider bar, and distillery all within easy barhopping distance. 

Looking for more on Bellaire, Michigan? Check out the 17 Best Things to Do in Bellaire, Michigan

8) Hike Saugatuck Dunes State Park

One of Michigan’s most beautiful summer destinations is Saugatauk Dunes State Park, but did you know this park is just as beautiful in the winter? 

Strap on snowshoes and head out into the dunes to watch the ice form on Lake Michigan. Remember to never venture out on to shore ice on the Great Lakes! This ice is incredibly unstable, full of holes, and there are many rescues or recoveries every year. 

9) Head to Hocking Hills, Ohio

Ohio’s Hocking Hills is one of the most beautiful winter vacation spots in the Midwest. Hike to frozen waterfalls, explore caves with ice, and enjoy many of the unique cabin stays in the area! Stay at Glenlaurel Scottish Inn and Cottages and ski their cross country trails. Alternately, stay in one of the Hocking Hills Treehouse cabins. Be sure to hike to the incredible Ash Cave and to beautiful Cedar Falls.

Hocking Hills might be the best place to visit in the Midwest in the winter!

10) Visit Theodore Roosevelt National Park

Looking for a unique winter destination at the edge of the Midwest? Head out to Medora, North Dakota and venture into the badlands of Theodore Roosevelt National Park. 

Here you can watch the wild horses frolic in the snow and backcountry ski the frozen Little Missouri River then return to Medora for dinner and drinks!

Visiting Theodore Roosevelt National Park in the summer

11) Chase the Northern Lights in Northern Michigan

Did you know the Upper Peninsula of Michigan is one of the best place to see the Northern Lights in the Midwest? Head up to the shores of Lake Superior to enjoy unobstructed views to the North and bundle up to watch for the Northern Lights!

Northern Lights are most common near the equinoxes, making March a great time to chase the Northern Lights! Keep in mind that while the Northern Lights are relatively common in Northern Michigan, they are still overall fairly uncommon, with the most incredible shows happening only a few times a year. 

Finding winter hiking pants for women can be hard! Check out this guide to winter hiking pants for women 🙂

12) Visit Grand Marais, Minnesota

Looking for the cutest place to visit in the Midwest in the winter? Head to Grand Marais, Minnesota! This beautiful small town is home to Nordic Saunas, cross country skiing, cute Scandinavian themed buildings, and more!

Note that winter kayaking, and kayaking at all on Lake Superior, should only be attempted by experience coastal paddlers with deep water self rescue skills and the appropriate gear. Read about cold weather kayaking gear here .

Once a fishing village, Grand Marais is now the entry way to the Boundary Waters in the summer, and the dreamiest getaway for winter lovers in the winter. Watch a winter sunrise at Artist’s Point on Lake Superior, grab food at the unique My Sister’s Place, and be sure to hit the trails and check out some of the best winter hiking around. 

Pro-tip: most of the time on popular hiking trails, you won’t need snowshoes but you will want a pair of warm winter hikers paired with microspikes or Yaktrax

13) Head to Chicago, Illinois

Head to the big city to experience some of the most magical winter scenes out there! Head to Chicago and go ice skating downtown, check out the Magnificent Mile Lights festival, or visit Christkindlmarket in downtown for a German-inspired Christmas market.

14) Visit Traverse City, Michigan

Traverse City is one of the coziest places to visit in the winter in the Midwest with beautiful views of the Grand Traverse Bay, an abundance of places to eat, a quick drive to the Sleeping Bear Dunes, and more!

Spend the daytime exploring the Sleeping Bear Dunes National Lakeshore, or alternately walk the snowy shores right in downtown Traverse City. After, head to North Peak Brewing Company for delicious beer and food.

Check out a full guide to exploring the Sleeping Bear Dunes National Lakeshore in any season!

15) Winter Hiking in Silver Bay, Minnesota

Looking for the best winter hiking destination in the Midwest? Head up to Silver Bay, Minnesota for some of the most beautiful winter hiking, snowshoeing, and skiing!

Stop by locally-owned Timber Coffee Company for a warm-up before you hit the trails! For an easy route, tackle the beautiful Shovel Point trail and walk along ice covered cliffs— this trail is especially beautiful at sunrise when the frozen ice formations along the trail light up pink. 

For a more difficult route, head out to frozen High Falls on the Baptism river, an adventure that’s sure to be memorable!

Check out the best all-season hiking trails in the area!

16) Enjoy Door County, Wisconsin

One of the most beautiful places to visit in the winter in the Midwest is Wisconsin’s Door County, where Lake Michigan makes for some incredible Arctic scenes!

With ample cross country skiing, spas, and bakeries, Door County is a great winter destination for active couples and families alike. If you only do one thing, be sure to head to Cave Point County Park at sunrise for dreamy winter scenes. Be sure to stay on the trail and walk with care as ice over the lake can be dangerous!

17) Winter Camp in the BWCA

Looking to sleep under the Northern Lights, cook over a wood burning stove in the backcountry, and enjoy all of the beautiful winter sights the Boundary Waters have to offer? Head out to the BWCA in Northern Minnesota for a winter camping adventure!

This adventure requires some previous experience with winter camping!

18) Michigan’s Keweenaw Peninsula

Have you been to the snowiest place in the Midwest? Michigan’s Keweenaw Peninsula averages 300 inches of snow a year and is easily one of the best winter destinations in the Midwest for reliable snowfall, skiing, snowshoeing, and more!

Check out Michigan’s Keweenaw Peninsula in the winter!

Looking for more Midwest Vacation Ideas?

• Download the Midwest Adventure eBook Bundle for hundreds of waterfalls, campsites, ski trails, overlooks, coffee shops, and hidden gems throughout the midwest!
• Read about the best tings to do in Michigan’s Pictured Rocks
• Check out the best day hikes on the shores of Lake Superior
• Want real hiking, paddling and travel stories delivered right to your inbox? Join the Hello Stranger newsletter community

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