6 of the Best Small Towns in the Midwest to Live In
There’s something special about small-town living, shaped by its friendly atmosphere, natural beauty and slower pace that gives you room to breathe.
Beyond their charm, these towns are also practical places to put down roots. Whether you’re raising a family, planning for retirement or simply looking for more balance while you work, small towns provide everyday essentials that support life at every stage.
Across the Upper Midwest, small towns are offering a fresh take on what home can mean. If you’ve been dreaming about a lifestyle that feels more grounded, these six towns invite you to explore what small-town living has to offer.
1. Galena, Illinois
Tucked into the rolling hills of northwest Illinois, Galena is a historic gem filled with 19th-century charm and scenic character. With its brick-lined main street, Victorian homes and sweeping views of the Mississippi River valley, it feels like stepping into another time.
Locals enjoy boutique shopping, wineries and access to nearby parks and bluffs for hiking and cycling. The recently expanded Midwest Medical Center brings a wide range of rural healthcare services close to home. Safe neighborhoods, affordable housing and a welcoming community make Galena a peaceful place to settle.
2. Stillwater, Minnesota
Located along the St. Croix River just a short drive from the Twin Cities, Stillwater blends historical charm with modern comfort. Stroll the downtown district and you’ll find restored brick buildings, antique shops, riverside dining and local festivals that bring neighbors together.
Residents enjoy blufftop trails, picturesque parks and walking paths that cross the historic Stillwater Lift Bridge. With nearby healthcare facilities, high-performing schools, commuter-friendly transit and a thriving arts scene, Stillwater offers the beauty and ease of rural living while staying well-connected to everyday essentials.
3. Viroqua, Wisconsin
Nestled in the heart of Wisconsin’s Driftless Region, Viroqua is a thriving small town known for its rolling farmland, organic agriculture and vibrant food culture. Home to the renowned Driftless Café and Viroqua Food Co-op, the town draws chefs, farmers and foodies alike for its farm-to-table flavors and deep-rooted connection to the land.
The downtown district features locally owned galleries, shops and cafés that reflect the town’s creative spirit and community values. With affordable homes, well-rated schools and a strong focus on sustainability, Viroqua blends rural simplicity with intentional living.
4. Princeton, Illinois
Set among the quiet fields of north-central Illinois, Princeton is a welcoming town where local pride runs deep. Its revitalized main street is lined with murals, boutiques, bakeries and family-run restaurants, while seasonal events like Festival 56 and rotating exhibits from the Prairie Arts Center keep the community connected.
Locals enjoy access to nearby green spaces like Zearing Park and Mautino State Fish and Wildlife Area, a strong public library and convenient Amtrak service to Chicago. With affordable housing options, low crime rates and a blend of small-town values and creative spirit, Princeton offers a peaceful place to plant roots and build a life not far from major cities.
5. Red Wing, Minnesota
Tucked along the Mississippi River and framed by scenic bluffs, Red Wing is a historic town known for its creative roots and riverfront beauty. Its walkable downtown showcases 19th-century architecture, locally owned shops and cultural landmarks like the Sheldon Theatre and Red Wing Shoes.
Locals take in panoramic views from Barn Bluff and Cannon Valley Trail, and benefit from quality healthcare through Mayo Clinic, high-performing schools and accessible housing options. Just over an hour from the Twin Cities, Red Wing blends culture, community and comfort with the ease of small-town living.
6. Bayfield, Wisconsin
Perched along the bluffs of Lake Superior, Bayfield is a lakeside community known for its beauty, creativity and connection to nature. Residents enjoy easy access to the Apostle Islands, berry farms, quiet trails and small-town gatherings that bring the town to life. From summer concerts at the Big Top Chautauqua to fall orchard visits and winter hikes to the sea caves, there’s always something close to home to enjoy.
With a thriving artist community, walkable downtown and low crime rates, Bayfield offers a peaceful pace and a lifestyle deeply connected to the great outdoors.
A Life Rooted in Possibility
From scenic river towns to rolling acres of farmland, these six communities offer more than rustic charm. They offer a place where you can build the life you’ve been dreaming about.
At Compeer Home, we know moving to a small town is more than just a change in scenery. It’s about stepping into a new way of life. Explore tips, guides and real stories from people who’ve made the move on our rural lifestyle page.
Ready to take the next step? Try our Loan Finder tool to see which financing option fits your dreams.
