There’s something to love about all four seasons in the beautiful Midwestern State of Wisconsin – but fall’s breathtaking beauty is undeniable. There are plenty of big-name attractions in Wisconsin, including Door County, the Apostle Islands National Lake Shore, and popular towns like Madison and Milwaukee. However, there are even more small towns in Wisconsin that offer incomparable retreats and a remarkable array of things to do in the fall. Wisconsin truly is the ultimate Midwest destination to visit this fall!
As the leaves change color, small towns in Wisconsin transform into vibrant destinations that draw in visitors with their beauty and warm hospitality. Whether strolling through historic downtowns or exploring the scenic countryside, the crisp autumn air and stunning landscapes make fall getaways in these quaint towns an experience like no other. From the shores of Lake Michigan to the rolling hills of Wisconsin’s scenic Driftless Area, there’s something magical about visiting off-the-beaten-path destinations and exploring Wisconsin’s many hidden gems.
The best part about visiting small towns in Wisconsin is the people you’ll find there. Each town has its own unique personality, offering a mix of outdoor activities, local festivals, and cozy cafes – but more importantly, each town will embrace you with the signature warm Wisconsin hospitality you expect. That’s particularly true if you stay at one of the many Wisconsin Bed and Breakfasts, Inns, and Boutique Hotels associated with the Midwest Association of Independent Inns. It’s no secret that Wisconsin is home to some of the best places to stay in the Midwest, including a range of unique properties.
Whether staying in a charming Victorian B&B or a modern boutique hotel, you’ll find that the attention to detail and local flavor in these places add an extra layer of enjoyment to your fall getaway. Slow down and explore with us this fall. Book your Wisconsin getaway today!
The Best Small Towns in Wisconsin for Fall Getaways
There are, of course, plenty of things to do in Wisconsin this fall. If you’re looking for a refreshing break away from crowded tourist hotspots, we encourage you to embrace travel to one (or more) of the many small towns in Wisconsin this year. Basing your trip in small towns will still allow you to enjoy Wisconsin’s breathtaking fall beauty but at a more relaxed pace. More importantly, you’ll find the true spirit of Wisconsin in these small communities.
Hidden gems can be found around every corner in Wisconsin. From quaint cafes and local shops to fascinating museums and awe-inspiring fall beauty, small towns in Wisconsin are a special part of the fabric of the Midwest. Experience some authentic Wisconsin charm, engage with locals, attend vibrant festivals and events, and seek the unique. Below, we’ve listed some of the best small towns in Wisconsin that would make for an exceptional fall getaway!
- One of the best small towns in Wisconsin is just a short 30-minute drive north of Milwaukee. Cedarburg‘s historic downtown, lined with 19th-century buildings, is inviting any time of year but positively gorgeous in the fall. Each autumn, the town hosts the annual Wine & Harvest Festival, where you can enjoy local wines, food, and crafts. Strolling through the town’s shops and visiting the Cedar Creek Settlement, a restored woolen mill now housing boutiques and restaurants, are highlights of any visit to Cedarburg.
- Experience Wisconsin’s scenic driftless area in the town of Viroqua. This charming Wisconsin town is a hub for organic farming and local arts. Visitors can enjoy hiking, shopping at the farmers market, and exploring the town’s vibrant arts scene. The Driftless Area Art Festival, held in September, showcases local artists and artisans.
- Though popular cities in Door County will no doubt be busy in the fall, you can still enjoy the small-town charm you’re looking for when visiting another of our favorite small towns in Wisconsin: Egg Harbor. Egg Harbor is a picturesque fall getaway with stunning shoreline views and some of Wisconsin’s best fall colors. Visitors can explore local wineries, hike in nearby parks, and enjoy outdoor art installations. Join us in Door County to celebrate fun events like the annual Autumn Lighthouse Festival or Egg Harbor’s Pumpkin Patch Festival, both in October.
- Another of Wisconsin’s most popular northern small towns is Bayfield, the gateway to the breathtaking Apostle Islands. In the fall, visitors can explore orchards for apple picking, enjoy scenic drives along the lake, and take ferry rides to the islands. The Bayfield Apple Festival in October is a must-visit.
- Craft beer fans won’t want to miss the southern Wisconsin town of New Glarus. Known as “America’s Little Switzerland,” New Glarus is perfect for a fall visit with its Swiss-themed architecture and rolling countryside. The town’s Oktoberfest is a highlight, offering traditional music, food, and dancing. Don’t miss a visit to the New Glarus Brewing Company for a taste of the town’s famous beers.
- For rugged, adventure-forward small towns in Wisconsin with a surprising art scene, don’t miss a visit to Wausau. Enjoy gorgeous fall colors from the peaks of Rib Mountain State Park or hiking trails through the scenic woods of Wausau – but don’t miss the town’s art scene, either. Home to fantastic museums like the Leigh-Yawkey Woodson Art Museum, the depth of experiences waiting for you in Wausau is exceptional.
- Mineral Point, in southern Wisconsin, is another favorite for authentic Wisconsin charm. This historic mining town is ideal for a fall getaway with its well-preserved architecture and artistic community. Visitors can explore galleries, shops, and the historic Pendarvis site. Mineral Point hosts a Fall Art Tour, where visitors can meet local artists in their studios and purchase unique works.
- Spring Green is a charming small town on the lower Wisconsin River, not too far from the iconic House on the Rock and Frank Lloyd Wright’s Taliesin. With so many things to do in the area, it’s no wonder this is one of the most popular small towns in Wisconsin.
- Treat yourself to breathtaking beauty along Wisconsin’s Lake Michigan shoreline, and visit the quaint town of Two Rivers. With pristine beaches and plenty of local history, this is the perfect place to recharge and relax this fall. Join the town for the 40th annual Two Rivers Applefest in October.
- Finally, head into the center of the state and enjoy one of our favorite small towns in Wisconsin, Waupaca. During the summer, Waupaca is packed with people visiting the Chain O’ Lakes, but during the fall, you’ll find that charming small-town ambiance you crave in getaways. With plenty of untouched natural areas to explore, the fall in this part of the state is breathtaking. Each October, the city comes to life with the annual Chain O’ Lakes Blues Festival.
The Best Places to Stay in Wisconsin
Whether you’re looking for fall getaways centered around outdoor experiences and breathtaking fall colors, or you’d prefer an art-forward destination that offers the best in regional art, there are plenty of great small towns in Wisconsin worth visiting this fall. Wherever you plan to go, you’ll likely find nearby accommodations associated with the Midwest Association of Independent Inns. We offer some of the most unique places to stay in the Midwest, including a fantastic range of Inns, hotels, cabins, and Bed and Breakfasts in Wisconsin.
Choose to stay among our collection of Wisconsin Bed and Breakfasts, Boutique Hotels, and Cabins, and you’ll enjoy an authentic slice of Wisconsin hospitality. Our dedication to excellence is unmatched. We offer one-of-a-kind lodging experiences that go far beyond the traditional hotel experience you’ll find at larger properties, let alone the impersonal and unpredictable guest experiences you’ll find among Airbnb and VRBO vacation rentals. Our collection of Midwest Inns is diverse, too, including everything from urban vacation rentals and working farms to historic estates and solitary cabins.
Whether on a solo adventure or traveling with your family, there’s no better place to stay in Wisconsin. Whether enjoying a fresh start each morning with homemade breakfast featuring locally sourced ingredients or thoughtfully curated guest experiences to enhance your fall getaway, our Innkeepers are passionate about hospitality and ensuring you have the best fall getaway imaginable. What awaits you in these small towns and unique places to stay is an unforgettable connection to our local culture. If this is what you’re looking for this fall, it’s time to book your stay at one of our exceptional Bed and Breakfasts in Wisconsin.
