The 10 Cutest Small Towns in the Midwest

The Best Small Towns in the Midwest

1.Egg Harbor, Wisconsin

With a population of just over 200, Egg Harbor, Wisconsin, in the state’s picturesque Door County peninsula, is the model cute midwestern small town. It’s also located about just halfway up the long peninsula, and directly on Green Bay, making it a perfect waterside destination for anyone who wants a small town getaway.

“[Egg Harbor] is quintessential Door County, and its location in the middle of the peninsula makes it an easier town to get to for anyone traveling from the Midwest or further afield,” says travel writerAgnes Groonwald.

The town offers every amenity that someone would want out of a trip to Door County—stunning water views, fun breweries, and of course, your own Wisconsin-made cheese straight from the Dairy State to take home from Door Artisan Cheese Company.

2. Amana Colonies, Iowa

Visiting the Amana Colonies in east-central Iowa isn’t just taking a trip to one small village, or even the seven villages that make up the colonies. Instead, you’re taking a trip to a version of utopia for some German Radical Pietists, who broke away from the Lutheran church and formed their own community in the midwestern state in 1855.

“This adorable [area] is lined with one of a kind locally run shops, unique places to eat an old-fashioned meal and plenty of nostalgia for visitors,” says Melissa Dixon, a travel blogger at Thirty Something Super Mom. “The streets are lined with lanterns, the businesses are made of brick, stone and clapboard, creating an ambience of yesteryear. Visitors can step inside an original general store that houses the original glass topped display cases and wooden floor from the mid 1800's.”

The colonies were a hub of communal living with a self-sufficient local economy for several decades, and have been listed as a National Historic Landmark since 1965. Nowadays, they’re a tourist attraction that is much loved for its unique shops filled with handcrafted items and as an area with an extremely unique history.

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3. Hamilton, Ohio

Not far from Cincinnati in the southwest corner of Ohio, Hamilton is a relatively small city with a lengthy history. Originally established as a military fort named after Alexander Hamilton, the city sits on the Great Miami River and is one of the cutest destinations in the Midwest.

“It has a beautiful and walkable Main Street and High Street Corridor that’s lined with lovely shops, restaurants, and parks,” says Tracy Kocher, the vice president of marketing and communications at Visit Butler County. “The beautiful Great Miami River flows through this area and there’s a walkable bridge that joins both halves.”

But it’s not just stunning river views that attracts visitors to Hamilton. The city is well-known for its sculptures, and you can see many on display at the Pyramid Hill Sculpture Park and Museum, which is home to more than 70 permanent pieces of art and a rotating series of exhibitions.

4. Beatrice, Nebraska

Just because Beatrice, Nebraska is a small city, with an area of under 10 square miles, doesn’t mean that there isn’t a lot to do. In fact, the southeastern Nebraska city packs a lot of activities in its tiny area.

“Beatrice has Homestead National Historic Park which marks the first homestead site claimed under the Homestead Act by Daniel Freeman,” says Megan Bartz, the tourism coordinator at Beatrice Area Chamber of Commerce. “Over the last decade there has been a lot of revitalization efforts resulting in unique boutique shopping, a brewery and speakeasy, and beautiful hiking, biking, walking, running and cycling trails for all to enjoy.”

The charming small city is also the county seat of Gage County, and in addition to its small-town charm, Beatrice also houses stunning buildings like the Gage County Courthouse, a striking Richardson Romanesque building constructed in 1892 that has been on the National Register of Historic Places since 1990.

5. Winona, Minnesota

Take a look around most big cities and you’ll see that they’re modernizing as they grow, upgrading old buildings and sadly, stripping away some of the charm. Thankfully, Winona, Minnesota doesn’t have that problem. Its downtown area, filled with buildings constructed in the Victorian commercial architecture style makes it one of the cutest small cities in the Midwest.

In addition to its charming downtown, Winona is home to Winona State University, a public university with approximately nine thousand students. The school makes the city, which has a population of just 25 thousand residents, feel like a cute college town rather than a bustling city.

Not only does Winona have a cute small-town main street, filled with shops, cafes, and public buildings, but it’s also set in a beautiful location. The city is on the Mississippi River, just over the border from Wisconsin, and it’s surrounded by bluffs including Sugar Loaf, a 500-foot tall bluff that towers over Lake Winona.

6. Nashville, Indiana

It’s not the Nashville you’re thinking of, although Nashville, Indiana, located in the southern portion of the midwestern state, is just as artistically-inclined as the larger city that shares its name. The town, which has a population of just over 1,200, is known for its arts scene and its specialty shops and bed and breakfasts, which attract many visitors.

“[Nashville] is a quintessential and exemplary little town that [has] plenty of trees, lovely people, and an old antique vibe,” says Lokesh Pant, a travel expert and the CEO of Bargain Air Ticket.

The town is the hub of the Brown County Art Colony, which encourages many artists in Indiana and the Midwest to visit and paint. While the colony was officially established in 1907, artists have been moving to Nashville and using the small town as a muse since the 1870s.

7. Mackinac Island, Michigan

Part of Mackinac Island’s charm and overall cuteness is the nostalgic feeling it evokes in visitors. Mackinac Island, located in Lake Huron, is completely devoid of chain restaurants, hotels and stores, as well as cars. The island is a tourism hotspot in the Midwest, but the permanent population hovers around 500 residents, making it one of the most popular small towns in the country.

Mackinac Island is most well-known for its majestic Grand Hotel, a massive, historic hotel that has hosted five U.S. presidents since the late 19th century. But that’s not the only place to stay on the charming island, which is home to dozens of hotels and bed and breakfasts, including the Mission Point Resort.

“With a ban on motor vehicles, Mackinac Island limits modes of transportation to horse-and-buggy, walking and biking, making visitors feel as if they’ve stepped into a forgotten time,” says Liz Ware, the vice president of sales and marketing at Mission Point Resort. “More than 80 percent of the island is protected as a state park, creating more than 70 miles of hiking and biking trails through which to explore the island’s natural beauty, from coniferous forests to rocky shorelines. Victorian-style cottages dot the bluffs of Mackinac Island, and the small but bustling downtown area is filled with shops boasting goods from handmade fudge to locally crafted jewelry. “

Mackinac Island is only reachable by private boat, ferries that leave from St. Ignace in the Upper Peninsula or Mackinaw City in the state’s Lower Peninsula, or by plane, as the island has its own small airport. The main tourist season is from May through October, but the island is open for visitors all year-round, with events like the island’s Christmas Bazaar happening in the beginning of December, and the Twilight Turtle Trek, a ski and snowshoeing trek taking place in January.

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8. Pella, Iowa

People don’t normally travel to the Midwest for a European experience, but that’s exactly what visitors to Pella, Iowa will get. The town, settled by Dutch immigrants, pays tribute to this heritage with its canal, windmills, and Dutch-themed stores, and is as close to an experience of visiting the Netherlands that you can get.

“It's an excellent destination for a day trip option or weekend escape to enjoy the Gouda Cheese from Frisian Farms Cheese House and enjoy Dutch-inspired spots and treats from Vander Ploeg Bakery & Jaarsma Bakery, Ulrich's Meat Market, and Dutch Fix for a Dutch culinary experience,” says Owen Redford, the founder of travel website Things to Do.

9. Augusta, Missouri

The Midwest isn’t typically known for its sights and vistas, like other regions of the country that are set in mountains or along the coast, but Augusta, Missouri is a bit different. The small town, not far from St. Louis, attracts visitors every fall because of its stunning scenery, which is just part of what makes Augusta such a cute town.

“As you enter Augusta, you may feel like you are stepping into a small town USA movie set,” says travel writer Casandra Karpiak, the co-founder of Savoteur. “Visitors can stroll the idyllic downtown, hop on the free trolley to go wine tasting at the local wineries, rent bikes to spend a day on the Katy Trail, or relax on one of the many patios overlooking the stunning fall foliage throughout the valley.”

Augusta, with a population of just over 200, is a popular stop along the Katy Trail, a bike and walking trail that extends for more than 220 miles along the Missouri River.

10. Woodstock, Illinois

While Phil Connors, Bill Murray’s character in the 1993 film Groundhog Day, might have resented waking up in the same place every day, residents of Woodstock, Illinois, where the movie was filmed, don’t seem to mind, because of the small-town charm found in the northern Illinois town.

Although you could possibly do the same thing over and over again every day, there are so many things to do in the small town that it’s not mandatory. Spend a day in the fall picking apples at All Seasons Orchard, or partake in some small-town fun antiquing and hitting up local, family-owned restaurants.

Or visit the town in the beginning of February to take part in the annual Groundhog Days festival, which pays tribute to the movie that made the town famous, and the holiday it was named for.