Often times, big city life can take a toll on any person—which means that guys and gals craving for the charm, appeal, and away-from-it-all vibe of the Midwest will definitely relish in the numerous idyllic weekend escape options scattered in and around the entire region. Forget New England, because the Midwest has also got a fair share of adorably quaint communities that ooze with a unique charm all their own. During the summer season, these cozy little towns often double in size, promising travelers of all sorts the chance to relax, to unwind, and to take a break from all that city chaos.
Why not do some sailing and antique shopping, or fine dine amidst scenic views, tons of history, and flourishing culture? Whether you want a full-on B&B experience, an activity-filled lake excursion, or the chance to settle down with locals in an excluded artist colony, there are more than enough spots to head towards right in the middle of America. They might not be close to the Pacific or the Atlantic, or even the Gulf of Mexico, but that doesn’t mean these heartland treasures are any less spectacular than all those coastal destinations. Here are eleven of the cutest and most charming Midwestern towns worth visiting.
Take A Trip To These 11 Charming Midwestern Towns
Even famed American architect Frank Lloyd Wright fell so into love with the rolling hills of this Wisconsin favorite that he built his summer retreat Taliesin in the area. With majestic natural sights right on the banks of the Wisconsin River, the town of Spring Green is a summer paradise for sure—a small and quaint space to relax at just a mere forty miles from Madison.
Be charmed and surprised by this beautiful artisan community with a tour of the Hillside Home School, or by enjoying an evening of Shakespearean performances at the American Players Theatre. Be sure to stroll through Wright's home and to make time to dine on organic fare sourced directly from nearby farms at Spring Green General Store. You might even opt to stay at The Usonian Inn, a retro motel with modern perks that was designed by an apprentice of Mr. Wright.
It’s been named the bed-and-breakfast capital of Minnesota—but along with those charming B&Bs are tons of famous eateries, as well as a world renowned trail system. Three simple words can describe this Root River Valley favorite: agriculture, outdoors, and arts. So go savor a slice or two of those old-time pies at The Aroma Pie Shop with a glass of house made root beer from Pedal Pushers Café before working off all that grub by taking a long bike ride down the 60-mile-long Root River Bike Trail.
Lanesboro is just about 120 miles southeast of the Twin Cities and stands at the center of the area's best paved multi-use trails, which include the 18-mile Harmony-Preston Trail and the 42-mile Root River Valley Trail. Be sure to get a trail map before heading out and to visit the Little River General Store for supplies you’ll need for the adventure ahead. Then top off that busy afternoon by checking out the array of art galleries, seasonal farmers markets, and professional theater rounds, such as the annual Henrik Ibsen Festival at The Commonwealth Theatre in the evening time.
Framed by the gorgeous northwestern Illinois hills, this old lead-mining town was the home of the 18th U.S. President General Ulysses S. Grant before he lead Union troops into battle during the Civil War. It’s got an old world allure and has-- throughout the years-- managed to reinvent itself all while maintaining a classic middle America vibe that has helped it become the Midwest’s “premier destination getaway.” The centuries old buildings in the business district now house hundreds of stores filled with unique antiques, home accessories, and artwork, as well as over forty hotels, inns, and restaurants that continue to welcome travelers to the area for a historic getaway amidst tons of scenic landscapes and roads.
With plenty of wineries, golf courses, hiking, biking, boating, and other cultural activities awaiting you and the family to take part in, there’s tons to keep busy with both within the surrounding lush farmlands and vintage downtown spaces. Be inspired by nature overlooking the banks of the Galena River at this Jo Daviess County favorite. It’s an especially popular getaway for many Chicagoans, many of whom keep second homes in town.
Located on the "Art Coast of Michigan,” this culturally-infused town takes the beaches of the Great Lake State and adds a bunch of art galleries and music festivals throughout the year that continue to draw crowds from all over the county. It’s a mere couple-hour ride from downtown Chicago—a more than awesome spot to relax during the warmer months to escape the deadly heat of the Second City. All along Lake Michigan, you’ll find art galleries, fine-dining spots, and winery tasting rooms, such as Fenn Valley Vineyards, where you can treat yourself to a sample of surprisingly delicious local wine.
Why not take a class at the Saugatuck Center for the Arts, get into a groove at a music festival, or have your portrait painted in the village by one of the artsy residents? In and around every street corner, visitors will find original artwork adorning studio windows, and come across spectacular sculptures sitting right in the center of town. Local artists even set up shop at nearby Oval Beach in the summer to catch the best of those swimmers and sunbathers enjoying the white sandy beaches with the use of paint.
Nestled snuggly between the Sawtooth Mountains and Lake Superior, this scenic beauty has been named the top adventure town by National Geographic Adventure magazine, and also boasts the Grand Marais Art Colony. Whether you want to explore the wilderness or take a one-of-a-kind canoe-building or basketry course at the North House Folk School, you sure won’t find yourself short of things to do in this Cook County city that’s always buzzing with creativity.
Artists and otters alike call this gateway to the Boundary Waters Canoe Area Wilderness their home—which, by itself, hosts dozens of cozy restaurants such as The Crooked Spoon Café, as well as quaint little inns such as the five-room Gunflint Motel. Find yourself ultimately inspired and rejuvenated in this inviting and vibrant harbor village that was dubbed ‘America’s Coolest Small Town’ by Budget Travel Magazine. Photographers, painters, and other such artisans will revel in the endless artistic ambiance while munching on fresh Lake Superior fish al fresco at one of the town’s picturesque outdoor cafés. Don’t forget to make friends with those famous Marais otters playing out on the dock!
Just over fifty miles south of Indianapolis, it’s a heavenly haven of hills and forests that serves as home to numerous artists living and working in studios tucked within the town’s over two hundred shops in the countryside. Inspired by the vistas that spread from every hilltop in the area, this artists’ colony was founded by Indiana painter T.C. Steele, and much like its Tennessee namesake, it also a true food lover’s paradise.
From wine to fresh saltwater taffy, this Indiana town houses plenty of inventive farm-to-table eateries-- it also has a dynamic array of galleries and craft studios throughout town. Pop into Brown County Art Gallery for works by famed printmaker Gustave Baumann, or delight in a show at one of the many music and theater venues. Nashville is known as the ‘Artist colony of the Midwest’—and with just two iconic covered bridges and all but three traffic lights in the entire city, this historic Washington Township area will no doubt fulfill any Midwestern getaway desire.
Any trip to this sleepy Wisconsin town is like a nostalgic journey into the past. The entire area seems to have stayed in the era of the 1920s, with most of Ephraim's most famous boathouses, inns, and public buildings still featuring white-clapboard exteriors that remain picture perfect and fully intact. If you’re looking for a picturesque seaside backdrop complete with an old school charm, this Midwest treasure is the place to go.
Located in Door Country, the coastal space is tucked into the shores of Lake Michigan on Wisconsin’s east side, offering thirty-some beaches, five state parks, numerous lighthouses and golf courses, as well as two dozen galleries, plentiful boutique shopping options, and an equally amazing amount of good food. It’s one of those pretty little towns that seems to be plucked right from a colorful painting. Go enjoy a boat trip from South Shore Harbor before indulging in a famous scoop from Wilson’s Restaurant & Ice Cream Parlor. Plus, you sure won’t find any wild partying in this peaceful and more than wholesome town—since its founding, Ephraim has prohibited alcohol manufacturing and sales within the entire village, making it the only dry municipality in the state of Wisconsin.
With never-ending water activities, upscale dining options, and stunning Lake Michigan sunsets to gawk at, this idyllic Michigan spot is another perfect getaway, offering a chance to get some rest and true relaxation in a sleepy space with a post ‘resort town’ feel. Numerous art galleries and yacht-dotted beaches can be found in and around town, making it an easy choice for a family fun trips.
There’s also the Southwest Michigan Wine Trail, one of the main draws in this quiet Michigan town, which houses a fine collection of local wineries featuring highly acclaimed public tastings and some of the best, most fruitful of vines (and wines!).
This Swedish-founded town is truly a modern Stockholm and got its start in the 1970s, when artists discovered its beautiful shores along Lake Pepin and the Mississippi River. Travelers eager to explore the Great River Road will fall in love with the ample array of art galleries and shops, as well as the delicious Scandinavian foods and culturally-inspired festivals that always combine old-world heritage with new creative expression.
It’s a quiet and serene place to take a trip to—one of the best chances in the Midwest to getaway, to get inspired, and to get creative. Make sure not to miss a visit to The Stockholm Pie Company, a popular local eatery with every pie you could possibly imagine, or the Midsummer Swedish Festival, which has offers more than enough fresh Scandinavian food to get you through a day of maypole dancing and a night of bonfire bonding.
Linger in and around antique shops and tearooms while admiring stunning Victorian homes in this Carroll County town that’s roughly two hours west of Chicago. It’s often likened to New England and has got a remarkable concentration of historically and architecturally significant structures, including the Mount Carroll Historic District and the Campbell Center for Historic Preservation Studies near the south edge of town. Don’t forget to take in a show at Timber Lake Playhouse, Illinois' oldest professional summer-theatre company, or to check out the year-round haunted house at Raven's Grin Inn for a spooky treat! Flea markets are even held the first and third Saturdays of every month so that you can get in full touch with your inner Midwesterner.
There’s definitely a quirky and uber cute vibe all throughout this northwestern Illinois city—classic, elegant, pastoral, and a just a little bit weird, especially at the Victorian Mad Hatter-themed local antiques store and tea room, or the miniature horse farm just outside of town, where tiny creatures stand less than three feet tall.
An iconic romantic getaway for Chicago city dwellers, this one provides the very best of any Midwestern resort town for adults and kids alike. The entire area is a launching point for popular boat tours on the lake—not to mention some seriously jaw-dropping lakefront homes that dazzle the surrounding shores. Make sure to check out the historic Black Point Mansion to truly be amazed!
Adventure lovers can unite with a hike around the over twenty-mile perimeter of the Shore Path surrounding the lake. Soak in some more than stellar landscape views while paddling around in the waters during the summer months, or by skiing down the slopes in the winter. There’s a classic allure to this Walworth County favorite, and since the days of the Civil War (when wealthy Chicago families actually first started building their summer homes in the area), the family friendly resort community continues to boast tons of boutique shopping, spectacular spas, charming B&Bs, world class golf resorts, fine dining experiences, and historical sites for any kind of traveler to enjoy.
This article was written by Pamela Chan.