As summer starts to fade and the air picks up that unmistakable fall chill, the Midwest quietly turns into one of the most colorful and underrated regions in the country. If you’re planning Midwest weekend getaways this season, you’ll want to time it just right to catch the leaves as they explode into deep reds, bright oranges, and glowing golds. From the Northwoods of Wisconsin to the lakefront trails in Illinois and the rolling plains of Iowa, the region is packed with scenic drives and hiking trails that showcase Midwest fall colors at their peak.
The best part? You don’t need to travel far. Whether you’re based in Chicago, Minneapolis, or Des Moines, the ideal fall trip is just a short drive away. Unlike some of the more hyped fall destinations on the East Coast, the Midwest offers a slower pace and a more authentic experience. It’s easy to find hidden overlooks, charming small towns, and roadside farm stands without the crowds. The region shines in fall with crisp mornings, cider tastings, farmers markets, and that unmistakable crunch of leaves underfoot.
Midwest weekend getaways for couples, solo adventurers, and families alike are full of surprises, from scenic boat rides along the Mississippi River to local harvest festivals in places like Galena, Door County, and Stillwater. It’s not just about the views, either. You’ll find great breweries, farm-to-table restaurants, and boutique shops in the best Midwest cities to visit this fall, not to mention some truly fantastic Midwest tours and activities. To round out your trip, pair your leaf-peeping with a stay at one of our independently owned Inns, Bed and Breakfasts, boutique hotels, or vacation rentals.
Whether you’re planning a romantic weekend getaway or just need a comfortable base for your Midwest road trip, these properties offer warm hospitality, thoughtful amenities, and excellent access to the top places to visit in the Midwest this fall. With options across the region, you’ll have no trouble finding the best places to stay in the Midwest. Fall in the Midwest is short and sweet, so now’s the time to browse your options and book one of the best Midwest weekend getaways before the colors fade. Book your stay with us!
Don’t Miss These Midwest Weekend Getaways
There’s no better time to explore the heart of the country than fall, when the Midwest becomes a masterpiece of vibrant color and crisp, golden light. Whether you’re after cozy small towns, epic scenic drives, or outdoor adventures under a canopy of red and orange leaves, this region offers some of the most memorable destinations for Midwest weekend getaways. From peaceful lakeshores to dramatic forested bluffs, the landscape is as diverse as the experiences.
Fall is the perfect season to slow down, explore somewhere new, and soak up the simple pleasures of the season, from savoring hot cider and taking colorful hikes to discovering charming towns and vibrant communities. Below, you’ll find some of the best Midwest weekend getaways to take this fall, whether you’re traveling for romance, adventure, or just a much-needed change of scenery.
Door County, Wisconsin
This peninsula, situated between Green Bay and Lake Michigan, is a classic fall destination in Wisconsin. The drive up Highway 42 is stunning in October, especially near Fish Creek and Ephraim, where colorful trees line the water. Explore local orchards, hike in Peninsula State Park, and stop into art galleries and farm markets along the way. For cozy lodging, stay in one of our Door County Bed and Breakfasts and enjoy easy access to fall festivals and scenic overlooks. This is one of the best Midwest weekend getaways for couples who love charming small towns and lake views.
Bayfield and the Apostle Islands, Wisconsin
For a more outdoorsy fall trip, head north to Bayfield and the Apostle Islands. The town is laid-back and artsy, and in the fall, this lakeside community comes alive with color. Kayak along the shore, take a boat tour, or hike to scenic overlooks in the Chequamegon National Forest. This is one of the top places to visit in the Midwest for travelers, especially if you’re looking for a little peace and quiet with a side of colorful adventure.Â
North Shore of Lake Superior, Minnesota
From Duluth to Grand Marais, the North Shore of Minnesota is packed with rocky cliffs, state parks, waterfalls, and some of the best hiking in the region. Gooseberry Falls and Tettegouche State Park are magnificent and among the best Minnesota State Parks to visit in fall. Scenic Highway 61 hugs the lake, making for an unforgettable Midwest road trip with endless foliage. Fall getaways in the Midwest don’t get much more scenic than this!
Stillwater, Minnesota
Located on the St. Croix River just outside the Twin Cities, Stillwater is an underrated gem in fall. Historic buildings, river cruises, and scenic bluffs make it perfect for a relaxing weekend, especially for couples who are looking for a bit of one-on-one time away from their otherwise busy demands. Grab brunch downtown, browse antique shops, and watch the leaves turn from a rooftop bar or cozy inn. It’s one of the best Midwest weekend getaways for couples looking to slow down and soak up small-town charm.
Decorah, Iowa
This Driftless Region favorite is surrounded by rolling hills and bluffs that offer stunning fall views. Go hiking at Phelps Park, rent bikes for the Trout Run Trail, or visit the famous Seed Savers Exchange. Decorah also has a surprising number of craft breweries, good food, and a strong Norwegian heritage. It’s one of the most unique Midwest vacation spots for travelers who like a side of culture with their fall colors.
Galena, Illinois
Galena is a historic town with preserved 1800s architecture, boutique shopping, and romantic places to stay, and is perfect for a classic fall escape. The hills around Galena come alive in October, and nearby parks, such as Apple River Canyon State Park or Mississippi Palisades State Park, offer great hiking and stunning views. It’s a favorite for couples, easily ranking among the best places to visit in the Midwest for leaf peeping and local flavor.
Starved Rock State Park, Illinois
Just two hours from Chicago, Starved Rock State Park is packed with canyons, cliffs, and waterfalls surrounded by dense forests. It’s one of Illinois’ most popular state parks, and for good reason. The foliage here is bold, and the views from the bluff trails are incredible. After hiking, stay nearby in a rustic lodge or a charming bed and breakfast to round out your Midwest weekend getaways.
Indian Cave State Park, Nebraska
There are plenty of fall colors to enjoy in Nebraska, too. If you’re up for an outdoor adventure, Indian Cave State Park near the Missouri River is a great fall destination. The park’s hiking trails take you through hardwood forests and along ridgelines with sweeping views of the changing leaves. The namesake cave adds a touch of history, and local lodging options include rustic cabins and quiet Midwest bed and breakfasts nearby.
Kettle Moraine Scenic Drive, Wisconsin
Stretching for 115 miles through southeastern Wisconsin, the Kettle Moraine Scenic Drive is a favorite for Midwest road trips. The drive rolls past glacial hills, hardwood forests, and peaceful lakes. It’s especially colorful in October, and there are plenty of trails and small-town diners to break up the trip.
Great River Road, from Minnesota to Illinois
Following the Mississippi River along the Great River Road from its northern roots as far south as you want to take it is one of the best Midwest weekend getaways you can take. This scenic route spans multiple Midwestern states and offers some of the most breathtaking fall drives in the region. Towns like Red Wing, Minnesota, and La Crosse, Wisconsin, make for great weekend stops along the way.
Baraboo & Devil’s Lake State Park, Wisconsin
Devil’s Lake State Park and the Baraboo Area consistently rank as one of the top places to visit in the Midwest for fall hiking. The towering quartzite bluffs at Devil’s Lake offer epic views over tree-covered valleys that blaze with color in October. Baraboo itself is quirky and fun, with vintage shops, local dining, and a connection to Ringling Brothers circus history. It’s an ideal fall weekend for travelers who love a little adventure.
Lanesboro, Minnesota
This small-town charmer in southeastern Minnesota is in the heart of the Driftless Region. Bike the Root River Trail, explore local art galleries, and take a scenic canoe ride or walk through the hills for unbeatable foliage. Lanesboro is often referred to as one of the most romantic Midwest weekend getaways for couples, especially in fall.
The Best Lodging for Your Fall Getaways
Knowing where to go is just the beginning. You also have to know where to stay, because your lodging can turn a good trip into a great one. That’s where the Midwest Association of Independent Inns comes in. Our member Bed and Breakfasts are located throughout the region, close to the very best places to visit in the Midwest for fall color. Whether you’re road-tripping along Lake Superior, wine tasting in communities around the Midwest, or hiking through the hills of Wisconsin, you’ll find the perfect place to stay nearby.
From historic Victorian mansions and cozy cabins in the woods to elegant city inns and countryside bed and breakfasts, our properties are anything but ordinary. Each one is independently owned and thoughtfully operated, offering a warm welcome, personalized service, and amenities that go beyond the basics. These are the kinds of stays that elevate your experience with amenities like locally sourced breakfasts, fireplaces to warm up by after a chilly hike, and hosts who know the best fall drives and hidden gems nearby. If you’re planning Midwest weekend getaways for couples, many of our properties even offer romantic touches like in-room spa tubs, wine packages, or private porches with a front-row seat to the fall show.
What makes these properties even more special is their connection to place. When you choose our Bed and Breakfasts and Inns, you’re tapping into the local character, charm, and culture that make each destination unique. Our members take pride in sharing what makes their corner of the Midwest worth discovering. So whether you’re craving quiet fall getaways off the grid or weekend adventures filled with local flavor, we’ve got you covered. Explore our full collection of independent inns, boutique hotels, cabins, and B&Bs, and book your Midwest fall getaway today. The leaves won’t wait.
