The Midwest’s 5 Most Charming Small Towns

Have you considered a getaway in the Midwest?

Small towns in the Midwest are marked by a community’s zest for life, a love for their neighbors, and a desire for some good old-fashioned fun.

They’re also full of gorgeous and easy-to-explore nature areas, home to amazing lakes where the setting sun seems to set the sky on fire, and festivals aplenty. Big cities DO have their own appeal, with a plethora of fine-dining restaurants and museums.

But there’s just something about a small town that can charm you like nothing else. With scenic views, gourmet dining, history, and flourishing culture, these areas are charming escapes from the hustle and bustle of your busy urban life.

We’ve rounded up 5 small towns in the Midwest, positively bubbling with immense charm.

Copper Harbor, Michigan

You’ll find this lovely Midwest community right on the northern tip of Michigan’s Keweenaw Peninsula, with a humble population of only 136 residents. But don’t let that small number dissuade you.

This stunning place shouldn’t be overlooked, especially for those looking for prime access to Lake Superior. Outdoor lovers will undoubtedly find something to do here, with many opportunities for swimming, hiking, sailing, and even mountain biking.

And you can even take a ferry to the nearby Isle Royale National Park. Known for its hot summers and mild winters, Copper Harbor attracts all visitors year-round.

We also recommend checking out the Fort Wilkins Historic State Park with its restored 1844 military fort and barracks. This is the ideal outing for history-minded travelers.

Galena, Illinois

Located right on the border of Iowa, Minneapolis, and Wisconsin you’ll find this small Midwest town that promises quintessential charm and all kinds of fun throughout the year.

Galena’s rolling hills, historic charm, and scenic roads make for the perfect getaway to recharge your batteries. When you take a stroll down historic Main Street, you’ll feel like you’ve traveled 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.

Fun Fact: General Ulysses S. Grant called Galena home before leading his Union troops into battle during the Civil War.

A scenic town with a rich historical past, today’s visitors enjoy Galena’s many fine dining options, bed and breakfasts, and old-world allure.

In the wintertime, visitors can dabble in snowshoeing adventures, and come summer, you can take in a scenic hot air balloon race. And be sure to drop by the iconic 1826 Dowling House to witness impeccably preserved 19th-century buildings.

Lake Geneva, Wisconsin

Located about 80 miles northwest of Chicago, Lake Geneva is a pristine getaway home to lavish homes and lakeside estates. Situated on the banks of Geneva Lake, visitors can enjoy boat excursions over an 8-mile tour or stroll alongside the waterfront on a lovely boardwalk.

With glistening waters and crisp forested views, this Midwest town’s natural scenery is rivaled only by its fancy houses and charming small-town feel.

Lake Geneva is a pleasant place that’s full of restaurants, quaint shops, and warm hospitality. If you choose to visit in autumn, you can enjoy the water’s cool breezes, the changing leaves’ stunning colors, and fun activities like apple or pumpkin picking.

Chagrin Falls, Ohio

With a population of just over 4,000, Chagrin Falls was established in the 1830s and is a short 40-minute drive from Cleveland. Named after the cascade in the town, the Chagrin River also runs through this charming historic town in the Midwest.

Take a walk through the beautiful Main Street, where 19th-century building fronts are standard in this town, and browse a great selection of novelty stores, antique shops, and local art galleries.

In the spring and summer, visitors can enjoy festivals like the Blossom Time Festival or take in the sounds of different music concerts in the open air. For those who have a sweet tooth, stopping at the Chagrin Falls Popcorn Shop is a MUST.

You can try up to 16 different snack flavors, or buy some freshly made doughnuts, perfect to eat while taking a stroll or picnicking near the waterfalls.

Hill City, South Dakota

Hill City is just an hour’s drive away from Deadwood. And while it used to be the home of indigenous tribes over the centuries, the town was formally founded in 1876 as a mining hub and still maintains a splendid 19th-century charm.

History lovers and casual visitors alike will love the sites of two unique railroad interests: the Black Hill Central Railroad and also the South Dakota State Railroad Museum.

At Black Hill, you can take a ride on an authentic 1880 steamer, carefully restored and preserved, while at State Railroad Museum, you’ll get to hear an intriguing tale on the exploration of the development of steam engines in the Western US.

And since you’re already in the area, you should visit the iconic Mount Rushmore. It’s just a short 20-minute drive from town in Hill City, perfect for a stopover before or after.

Let us know in the comments if you live in the Midwest or have visited and wish to share another charming small town with us!

And if you’re a big fan of the Midwest, you might want to check this out: 4 Best Midwest Road Trips in the US