The Most Beautiful Towns In The Midwest

Tenney Park, Madison, Illinois
Tenney Park, Madison, Illinois | Photo by Dave Hoefler on Unsplash
Culture Trip

These stunning Midwest towns provide New England household names with a real run for their money. With scenic views, gourmet dining, history and flourishing culture, these towns are charming escapes from the hustle and bustle of busy urban life. Whether you crave a quiet bed and breakfast, scenic lake boating excursions or an excluded artist colony, this list has your Midwestern travel needs covered.

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Spring Green, Wisconsin

Spring Green, WI, USA

With its majestic rolling green hills on the banks of the Wisconsin River, it’s no wonder architect Frank Lloyd Wright built his summer paradise in the beautiful town of Spring Green, Wisconsin. Tour Taliesin, the renowned structure, which includes the Hillside Home School or take in an evening Shakespearean performance at the American Players Theater. Wherever the day takes you, this quaint small town a mere 40 miles from Madison is guaranteed to charm and surprise.

Ephraim, Wisconsin

A trip to Ephraim feels like a nostalgic journey into a decade long past. With its charming inns, boathouses and picture perfect white buildings, Ephraim boasts old school charm with a picturesque seaside backdrop. Visitors enjoy daily boat trips from South Shore Harbor or a famous scoop from Wilson’s Restaurant & Ice Cream Parlor, which recently celebrated its 100th birthday. Notable fact – since its founding, Ephraim has prohibited alcohol sales or manufacture within the village, marking its place as the only dry municipality in the state of Wisconsin.

Lanesboro, Minnesota

Nicknamed the bed-and-breakfast capital of Minnesota, Lanesboro is a paradise for the nature lover, culture enthusiast and foodie. Lanesboro boasts activities for the active traveler with its 60-mile winding Root River State Trail, coalescing with a spectacular waterfall at the edge of town. The internationally recognized Commonwealth Theater, famous for its annual Ibsen Festival, acts as the backdrop for this creative community. With its serene setting, numerous fine dining options and artistic flair, Lanesboro boasts a vibrant and cultural quality of life for residents and visitors alike.

Grand Marais, Minnesota

Boundary Waters Canoe Area, Gunflint Trail, Grand Marais

This inviting and culturally vibrant harbor village is a renowned artist colony, a destination many creatives call home for its infinite natural beauty and inspirational atmosphere. The town’s countless musicians, artists, photographers and artisans provide endless artistic ambiance to what has been dubbed ‘America’s Coolest Small Town’ by Budget Travel Magazine. Whether you are watching Marais’ famous otters play on the dock or enjoying fresh Lake Superior fish al fresco at one of the town’s picturesque outdoor cafes, Grand Marais is sure to charm.

Nashville, Indiana

Brown County State Park Road, Nashville, Indiana

A certifiable food and art-lover’s paradise, Nashville provides its visitors with everything from the freshest and most inventive farm-to-table dining establishments to a dynamic sprinkling of galleries and craft studios throughout town. Known as the ‘Artist colony of the Midwest’, Nashville provides year round antiquing, music and theater venues and artists working out of their quaint galleries. A town that has two iconic covered bridges and only three traffic lights, Nashville is sure to delight with its Midwestern charm.

Stockholm, Wisconsin

This Swedish-founded town came to life in the 1970s, when artists began to flock to Lake Pepin and the Mississippi River for a quiet and serene place to create. Soon after, travelers followed to explore the town’s bustling art galleries and shops, burgeoning foodie scene and creative local festivals. Don’t miss a visit to The Stockholm Pie Company, a popular local joint with every pie you could possibly imagine. Finally, if you visit around the summertime, be sure not to miss the Midsummer Swedish Festival which boasts Scandinavian foods, maypole dancing and a remarkable evening bonfire.

New Buffalo, Michigan

Beautiful lakeside New Buffalo offers the perfect vacation package – endless water activities, upscale dining and stunning Lake Michigan sunsets. An idyllic, sleepy spot with a post ‘resort town’ feel, New Buffalo’s yacht-dotted beaches and numerous art galleries make it an easy choice for a family destination. One of the main draws of this quiet town is the Southwest Michigan Wine Trail, a collection of wineries offering the fruit of their vines for highly acclaimed public tastings.

Lake Geneva, Wisconsin

Lake Geneva

An iconic romantic getaway for Chicago city dwellers, Lake Geneva offers the very best of a Midwestern resort town for adults and kids alike. The town serves as a launching point for popular boat tours of the lake that whiz past some seriously jaw-dropping lakefront homes. Lovers of land can take a hike around the 21 mile perimeter of the lake and soak in its stunning views. Whether lounging in the lake during warm summer months or skiing on the slopes during the wintertime, Lake Geneva’s classic charm will lure just about any traveler.

Madison, Wisconsin

Wisconsin State Capitol, Madison, United States

Even with a population of over 200,000 people, Madison maintains its small town feel, providing endless charm and fascination for locals and visitors alike. Centering around the University of Wisconsin-Madison, the town maintains a youthful feel given its hundreds of college bars, bookstores, music venues and affordable niche foodie spots. In the winter months, hundreds of people flock to the surrounding lakes for ice-skating, ice-fishing and cross-country skiing. It is during the warm summer months that the city comes alive, with popular weekly farmers markets, outdoor concerts and boating events on the four lakes surrounding the city.

Galena, Illinois

Galena, IL, USA

The rolling hills, historic charm and scenic roads of Galena, Illinois make for the perfect destination to unwind and recharge your batteries. Take a stroll down historic Main Street and feel as though you’ve gone back in time. With its stunning architecture inspired by French Colonial and Greek Revival, over 85% of the town is a preserved national historic district. The 18th U.S. President General Ulysses S. Grant called Galena home before leading Union troops into battle during the Civil War. A scenic town with a rich historic past, today’s visitors enjoy Galena’s numerous fine dining options, bed and breakfasts and its old world allure.

Culture Trips launched in 2011 with a simple yet passionate mission: to inspire people to go beyond their boundaries and experience what makes a place, its people and its culture special and meaningful. We are proud that, for more than a decade, millions like you have trusted our award-winning recommendations by people who deeply understand what makes places and communities so special.

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