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The Midwest’s 10 Most Charming Small Towns

Small Midwestern towns deliver easy weekend getaways from bigger cities, with art, nature, food, and culture worth the trip.

As someone who was born and raised in the Midwest and lived in Canada for more than 26 years, I’ve had the opportunity to visit many small towns in the Midwest. The most interesting places in the Midwest are not always those which people tend to brag about. Apart from the big cities, small towns provide an entirely different type of escapade where one can relax, be outside, and feel a connection with nature. These places show that you do not necessarily need a big vacation spot in order to have an extraordinary weekend. Many times, these are the most impressive places one can experience.

1 OF 10

Saugatuck

WHERE: Michigan

Without question, Saugatuck certainly lives up to its remarkable status, which is earned through its guests’ praise. Located beside the shores of Lake Michigan, it is a wonderful destination where one can have a great time enjoying sandy beaches, sand dunes, and an arts district all in the same area on the weekends. In summertime, summer events add some additional buzz to this tiny town. With its unique blend of outdoor nature and creativity, the town has something special that you would hardly see anywhere else around the Lake Michigan area. One may choose to climb up the sand dunes and enjoy the view or just use the chain ferry.

INSIDER TIPGo early to Oval Beach for a quieter experience, then take the chain ferry across the Kalamazoo River before the afternoon crowds build.

2 OF 10

Galena

WHERE: Illinois

Galena is like going back in time. Most of the town’s Victorian architecture still exists today, allowing one to feel the history in Galena even without visiting a museum or historical site. This, along with the town’s brick sidewalks, restaurants, and presidential mansion which once belonged to President Ulysses S. Grant, surely make this city attractive to history buffs. One could spend an entire day walking around the town, finding a new sight or attraction every few steps.

INSIDER TIPBegin the day in Galena’s Main Street when it’s still quiet, then leave the town in the late afternoon to enjoy a leisurely wine tasting at a nearby vineyard.

 

3 OF 10

Decorah

WHERE: Iowa

Decorah’s Norwegian roots shape nearly everything about it, from its festivals to its museums. Vesterheim Norwegian-American Museum is an important part of the cultural heritage of the city, whereas its surroundings provide hikers with many opportunities to enjoy nature walks, as well as ice fishing in Ice Cave Park. Nordic Fest is one of the events which help the people of Decorah reveal their community’s character. The surrounding landscape makes it just as appealing for outdoor trips as it is for cultural experiences.

INSIDER TIPPair a visit to the museum with a walk through Ice Cave Park, then stop by a local bakery for something fresh after.

 

4 OF 10

Stillwater

WHERE: Minnesota

Set along the St. Croix River, Stillwater blends historic charm with outdoor activity. There are antique stores and coffee shops along all the streets, and the opportunity exists to kayak or paddleboard on the river. There are so many craft breweries in the area that one could easily spend an entire weekend exploring them. With such a laid-back pace, and the river flowing directly through, it is easy to settle down in this place.

INSIDER TIPRent a kayak in the morning when the river is calmer, then spend the afternoon exploring downtown shops and cafés.

 

5 OF 10

Madison

WHERE: Indiana

Madison sits along the Ohio River with a downtown that’s easy to explore on foot. It’s not a busy town, which is one of its charms. In fact, a leisurely stroll in the afternoon can easily stretch out into a whole evening. There are galleries, stores, and coffee shops along the roads, and natural trails and scenic drives close by make for a change into the natural world.

INSIDER TIPTake a scenic drive along the river at sunset, then head back into town for dessert or coffee on Main Street.

 

6 OF 10

Mackinaw City

WHERE: Michigan

While considered the gateway to the island of Mackinac, Mackinaw City certainly makes for a worthwhile stop itself. Acting as the gateway to both the Mackinac Bridge and the surrounding scenery along with many chances for trying out the local fudge and seafood, it is far more than just an intermediary step on the road somewhere else. Tourists have the chance to explore the waterside area, take in their surroundings, and take things at a leisurely pace before moving on to other areas.

INSIDER TIPCatch the sunset with a view of the Mackinac Bridge, then plan an early ferry the next morning to Mackinac Island before peak crowds.

 

7 OF 10

Grand Haven

WHERE: Michigan

Grand Haven is a city that revolves around water. It’s well known because of its famous musical fountain and beaches. Visitors can choose between cycling or spending time on the lakeside as the area never lacks anything related to the life of the lake. The bustling downtown district provides an adequate amount of stimulation with stores and eateries that are just lively enough to keep things exciting while not being overwhelming.

INSIDER TIPPlan your day so you can stay for the evening musical fountain show, one of the highlights of the town.

 

8 OF 10

New Buffalo

WHERE: Michigan

New Buffalo is an easygoing escape along the southwestern shore of Lake Michigan. It covers everything from wineries to luxury boutique hotels, beaches to outdoor sports like cycling and golf, providing you with an all-inclusive package for the weekend. It offers you the chance to spend time outside, but at the same time gives you numerous places where you can unwind and enjoy yourself at the end of the day. The location is perfect because of its proximity to cities.

INSIDER TIPSpend the afternoon at a nearby winery, then head back toward the water for dinner and a sunset walk along the beach.

9 OF 10

Holland

WHERE: Michigan

Holland stands out for its strong Dutch heritage and seasonal traditions. Starting with the Tulip Time Festival all the way to the windmills and bakers in town, it is easy to see why the town has a unique character in contrast with other towns in the area. A combination of parks, waterfronts, and artisan stores make the town very ideal to spend the weekend in. The season will also dictate a unique atmosphere during each visit, particularly in springtime.

10 OF 10

Charlevoix

WHERE: Michigan

Charlevoix offers lake access, a walkable downtown, and some of the most unusual architecture in the region. Visitors will never run out of things to do, whether boating, fishing, or exploring the world-famous Mushroom Houses. Besides the lakeside recreation, there are plenty of other ways to have some fun outdoors. With all the water around the area and the architectural structures, it offers an entirely different appearance compared to others around.

INSIDER TIPVisit the Round Lake area in the evening for some great views of the waterfront area.