Hi, I’m Hannah - Product Manager at Guess Where Trips.
There’s something special about winter road trips in the Midwest - snow-dusted towns, cozy cafés, and scenic drives that feel made for slowing down.
These are my favourite Midwest routes to explore in the colder months, with a few tips along the way and cozy places to stay if you want to stretch your trip overnight.
Take a look at the map below to get a general idea of where these winter road trips end.
My Favourite Winter Trips in Ontario...
Taking this trip in the winter? Here are my tips for 'Art Trails & River Tales':
- Bring your winter gear: our "Scenic Sights" option on stop #1 has fantastic snowshoeing and cross-country skiing trails in the winter time, so bring your gear for some winter fun!
- Show your itinerary at the cafe on stop #2: you'll be able to take advantage of our exclusive Guess Where Trips discount on their latte flights!
- Note: our optional stop may be inaccessible during heavy snowfall, but our featured stop is totally magical and a great choice in the winter months!
- Embrace the cozy winter vibes: noth of our featured small town and our "Want to keep going?" suggestion are super cozy in the winter time (it was even named the "coziest place in America" in 2024!)."
- Go skiing & snowboarding after the 4th stop: Just 20 minutes from your 4th stop you'll find this premier ski & snowboard destination (they have gear rentals too!).
- Cross-Country ski fans will enjoy the groomed Cannon Valley Trail: which runs from Red Wing to Cannon Falls. Don't forget to purchase your Greater MN Ski Pass ahead of time!
- Catch amazing views of the frozen Mississippi River: which you'll be able to see from the nearby bluffs, particularly at this nearby state park!
- Reserve a heated igloo: you'll find this funky eatery near our 2nd stop!
Recommended Winter Stays for 'Art Trails & River Tales'
St. James Hotel
Luxury Indoor Pool Hot Tub Lake Pepin & Arcade (Air bnb)
Taking this trip in the winter? Here are my tips for 'Falls, Forests & Fables':
- If the weather is frightful, here's a tip: our cafe suggestion on stop #1 has a nearby drive-thru location for those days when you don't want to get out of the car!
- Be sure to bring good hiking boots and your snowshoes: we've got tons of great outdoor options on this trip and all of them offer winter hiking, snowshoeing trails, and picturesque frozen waterfalls for your winter IG feed.
- Our animal encounter suggestion on stop #4 is open year-round, weather permitting: they just ask you to call ahead of your visit to ensure they are open and that someone is there to greet you (find the info you need in your road trip booklets!).
- Enjoy craft cocktails: Warm up from the inside out at this cozy distillery near your 4th stop. Open for craft cocktails Thursday - Saturday.
- You can turn this trip into two-day adventure: This is a great trip to split up over two days as there are tons of outdoor adventures on every stop, so it's worth it to take your time and get the most out of each stop.
- Come back to the first stop later for dinner or a drink: this brewery & pub are near your 1st stop of the day, so not open in the morning but worth coming back to for dinner or a drink!
Recommended Winter Stays for 'Falls, Forests & Fables'
Starved Rock Lodge
The Bunkies
Taking this trip in the winter? Here are my tips for 'All Things Charming'
- Turn this trip into a winter getaway: This road trip is a great option if you've got winter weekend getaway plans in the Chain O'Lakes area of Illinois. You can do some of the stops on the way there (1-3) and take in stop 4 on your way back to the city.
- Visit a Hallmark town: our small town suggestion on stop #2 has been a filming location for 4 Hallmark movies, so you know that this trip will have all the cozy winter vibes!
- Be prepared: Wear good boots for a peaceful snowy walk on stop #1!
- If you're getting cold: warm up with a seasonal latte at our cafe suggestion on stop #3.
- Craving Italian?: this cozy Italian restaurant is near our 2nd stop and is worth a visit if you can get a reservation! (the Pope even dined here!)
- Winter, your way: find tons of great winter activities in Lake County, both indoors and out, that will make the perfect winter weekend!
- Choose your winter adventure: go for a winter hike or enjoy the looped cross-country ski trails at this State Natural Area.
Recommended Winter Stays for 'All Things Charming'
Cozy Cabin by Nippersink Creek
The Abbey Resort
Taking this trip in the winter? Here are my tips for 'Treats & Trails'
- Dress for the cold: bundle up and wear good winter boots as we've got tons of great trail options on this trip, perfect for a winter stroll. Our favorite? Our boardwalk trail suggestion on stop #1 is a show-stopper in winter!
- Go tobogganing: Be sure to bring your toboggan for some sledding at our "nature center" suggestion on stop #2!
- Enjoy tasty coffee: our brewery recommendation on stop #3 also serves up some of the best coffee in the area, so if you're not a beer person, we still recommend a visit for a warm winter latte!
- A winter moment you won't forget: Have you heard of the saying "when Hell freezes over"? Well, you just might get to experience that exact thing on this trip!
- For the bird lovers: bring some bird seed and head to Bird Hills Nature Areawhere local feathered friends will often eat right out of your hands!
- Fun for all ages: kids & adults alike will love getting up close with furry farm animals at Domino's Petting Farm. Open Friday - Monday, no advance purchase required.
- For outdoor lovers: the Border-to-Border Trail goes all through the area of this road trip and offers fantastic winter hiking and snowshoeing for any outdoor adventurers!
Recommended Winter Stays for 'Treats & Trails'
Chelsea House Victorian Inn
Camp Woodbury Cabin 4
Taking this trip in the winter? Here are my tips for 'Elegant Estates & Outdoor Art'
- Bring your snowshoes: our outdoor stops #1 and #3 are both free year-round and perfect for snowshoeing if there's enough snow! Be sure to bring your gear along.
- Plan ahead: free guided tours of the sculpture park on stop #1 are offered on the 1st and 3rd Saturdays of the month too if you're looking for a great day to go on this trip!
- A must-try bite: We've got a few fabulous eatery options on stop #2 to warm up, but my fave is home to the original steamed bagel! You've got to try it!
- A perfect pick-me-up: our "want to keep going" coffee house suggestion on stop #4 is quite possibly the CUTEST cafe I've ever been to; highly recommend visiting, and grab one of their seasonal lattes!
- Keep the adventure going: About 40 minutes from your final stop is this cute historic railroad that offers fun themed railroad adventures throughout the year!
- A winter highlight: Our 4th stop town has a "winterfest" every year, with Luminary Walks happening in January and February.
- Sip and savour: Wine lovers will adore this nearby farm & winery that offers sparkling wine, cocktails, and even delicious Sunday brunch!
Recommended Winter Stays for 'Elegant Estates & Outdoor Art'
Brick Street Inn
Kit’s Cabin - Log Cabin Retreat in Indianapolis
Taking this trip in the winter? Here are my tips for 'Cascades & Colors'
- Embrace the snow: Our featured option on stop #1 is the perfect winter wonderland! Wear good boots or bring your snowshoes for some winter fun!
- A historic lunch: Enjoy a cozy lunch at the historic mill on stop #2. It's so cute, you'll feel like you've gone back in time!
- End on a sweet note: We think ice cream is a year-round treat, so visit our dairy farm on stop #4 to end your day! (or grab a Rodeo Burger if that's more your thing...)
- For the Architecture lovers: enjoy a tour of Frank Lloyd Wright's Westcott House, which is beautiful covered in winter snow!
- Igloo dining? Yes, please!: This cool wood-fired kitchen and bar in Dayton offers igloo dining! Reserve now until the end of February 2026.
- A final stretch outdoors: Enjoy the mile-long boardwalk trail at this nature park that is just 20 minutes from your final stop! Bring good shoes or snowshoes!
Recommended Winter Stays for 'Cascades & Colors'
The Cozy Cabin at The Armstrong Homestead
The Wildflower House Yellow Springs
Taking this trip in the winter? Here are my tips for 'A Taste of Amish Country'
- Important note: While our "Before You Go" and website state that this trip is best done from March to mid-December, that is only because of a seasonal farm on stop #1. If you're okay to miss out on the farm animals, then the rest of this trip is fabulous in the winter time and would be so picturesque!
- Opt for the bakery on stop #1: instead of the farm, visit our bakery suggestion for a sweet morning treat! (note that this spot is cash only though so head to an ATM before leaving home!)
- Camera-ready stop: You'll love our optional photo ops on stop #3, which are absolutely gorgeous covered with winter snow.
- Step into the past: Our historic village suggestion on stop #4 makes for the perfect winter photo op and is certainly worth a visit!
- Trade the cold for a show: Head inside to escape the winter weather and enjoy some live theatre or music at the Ohio Star Theatre.
- A peaceful winter wander: Enjoy some winter trails, perfect for snowy strolls or snowshoeing, at the Norma Johnson Center.
- Satisfy your sweet tooth: you'll love this local favorite chocolate shop near stop #1!
- Art in the open air: Visit the Holmes County Open Air Art Museum for ever-changing outdoor art sculptures that can be explored year round.
Recommended Winter Stays for 'A Taste of Amish Country'
Treehouse Village - The Shack
Romantic Solar House
Author: Hannah Elias
Hannah is the Product Manager at Guess Where Trips. From product launch strategy to research & development (and even writing our Detour Diaries book!), she continues to find new ways to improve our road trip products for customers.
