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3 Winter Road Trips Worth Braving the Cold

Want to kick off the year with an adventure? These road trips are even better in the winter.

By Sarah Von Bargen on January 3, 2019

Eau Claire WI
Eau Claire / Photo Courtesy of Visit Eau Claire

Contrary to popular belief, you can take a road trip in the winter. With the right preparation and planning, hitting the road during the winter months can be a fun and unforgettable travel experience.

Looking for winter road trip ideas? Interested in a winter road trip but worried that everything along your route will be closed for the season? Worry no more!

We’ve put together three fun, doable winter road trip itineraries, and we even did the legwork to make sure our suggested stops are open year-round!

1. Minneapolis, MN, to Decorah, IA (150 miles)

About halfway through this gorgeous drive you’ll come upon the small town of Cannon Falls. Stop for a snack at the aptly named Hi Quality Bakery (the spritz cookies are particularly good!), then poke around the historic downtown and check out the Cannon River that runs through the city.

No road trip is complete without a photo of a strange roadside statue or novelty water tower, which means you should obviously take the extra five minutes to Instagram Rochester’s corn-shaped water tower.

If you packed your snowshoes or skies, stop at Forestville State Park and enjoy the 60+ miles of trail. Even if you didn’t bring equipment, you can explore the park and the restored buildings of Historic Forestville – the village that used to exist here.

Once you’re in Decorah, stay at the historic Hotel Winneshiek if you’re feeling fancy. If you’re more adventurous, stay in a converted train caboose on a horse farm (yes, you read that correctly). Wherever you stay, don’t miss the Vesterheim Norwegian-American Museum or the award-winning Toppling Goliath brewery.

2. Chicago, IL, to Mineral Point, WI (170 miles)

Whether you live in Chicago or use it as a jumping off point for a couple days exploring the Midwest, this route is a winner. Hit the road early and stop in Rockford for breakfast at The Stockholm Inn – try their Swedish pancakes with lingonberries or the salt herrings. If you’d like to stretch your legs without freezing your toes, check out The Nicholas Conservatory and Gardens for some tropical-temperature fun.

Stop in Monroe, WI to visit Minha’s Distillery. See how they make their products and warm up with (small) samples of their vodka, rum and gin.

Looking for offbeat attractions? The Toy Train Barn Museum in Argyle, WI, costs $5 and has 56 4.8-star reviews. You basically can’t afford to NOT go.

Once you reach Mineral Point, you’ll wonder why you haven’t been vacationing here for years. Hang your hat at the historic Brewery Creek Inn, The Mineral Point Hotel or this pretty vacation rental. Mineral Point has a very active arts community – explore the Wantoot gallery or Brewery Pottery.

Check out the events calendar for Shake Rag Alley Center for the Arts to see if they’re running any workshops you’d be interested in. Make sure you eat at least one meal at The Red Rooster cafe and order a famous Cornish pasty!

3. Boston, MA to Waitsfield, VT (190 miles)

Start your trip with breakfast at MaryAnn’s Diner in Derry, NH. It’s a classic 50s-style diner – shiny metal exterior and all – that serves huge breakfasts.

Next, take a little detour into Warner, NH, for the New Hampshire Telephone Museum. Worth the visit just to see your childhood curly-corded, rotary phone on display!

Queechee Gorge is beautiful any time of year and – bonus! – you can look at it without freezing because you can park nearby. You can admire Ottauquechee River and the frozen falls from the comfort of the beautiful Simon Pearce Restaurant while you warm yourself with one of their amazing cocktails.

In Waitsfield, stay and eat at the Tucker Hill Inn or The Inn at Round Barn Farm. If you’re looking for something a bit more budget-friendly, this three-bed Airbnb is just $95 a night!

Catch a meal and a movie at Big Picture Cafe and make sure you stop at Village Grocery for a serving of Creemee’s maple-flavored soft serve.

And, of course, there’s lots of good skiing in and around Waitsfield. Skiers should check out Sugarbush or Mid River Glen. Non-skiers can rent ice skates at Waitsfield’s Skatium outdoor ice skating rink.

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