Stretching from North Dakota in the west to Ohio in the east, America’s stunning Midwest is home to great lakes, mighty mountains and vast sweeping plains. Many of the towns here started as simple French fur trading posts, others as trading posts along the Santa Fe trail. It’s that combination of epic landscapes and eclectic history – and a dash of Midwestern hospitality – that make many of the small towns in this region perfect for a weekend break.
Read on for our favourite Midwest towns...
The gorgeous wooden buildings that make up Bentonsport’s charming historic district were built by Mormon craftsmen as they migrated west along the Mormon trail in the mid-1800s. The iconic bridge that spans the Des Moines River here dates from that time too and offers the most scenic way to approach the town by foot. Drop by Addie May’s for Indiana’s best fudge. And spend the night, if you dare, at the historic Mason House Inn, regarded as one of the most haunted places in Iowa.
The charming streets of this venerable mining town are literally steeped in history. Ulysses S. Grant famously called the place home. Rival presidential candidates Abraham Lincoln and Stephen A. Douglas gave speeches on the balcony of the DeSoto House Hotel in the 1850s. And more recently, Oprah included it in her list of charming small towns you must visit. It’s not hard to see why. The town is bursting with history, culture and art. And in winter, some of the best snowboarding slopes around.
The tiny town of Shipshewana in LaGrange County, Indiana is home to the third largest Amish population in the US. They live on farms that surround the town and chances are you’ll pass one of their distinctive buggies on your approach. Shipshewana is a local ‘hub’ for Amish businesses and a great place to sample the delicious baked goods the community produces. Stop by Menno-Hof for an interactive cultural experience. Or browse the expansive flea market that takes over the main street in summer.
Love this? Follow our Facebook page for more travel inspiration
Pella was founded by immigrants from the Netherlands in 1847 and continues to proudly display its Dutch heritage to this day. You can tuck into a Dutch letter, dusted with sugar and filled with almond paste, at Jaarsma Bakery; take a tour of the Vermeer Windmill or simply stroll along the gorgeous Molengracht Canal. Spring is particularly lovely. More than 300,000 colourful vibrant tulips bloom across the town and the annual Tulip Festival brings all kinds of Dutch jollity.
You might recognise this small town 60 miles (97km) northwest of Chicago more as Gobbler’s Knob, the fictional town featured in the iconic 1993 movie Groundhog Day starring Bill Murray. The town has certainly leaned into that with an annual Groundhog Day festival held every February. But there are plenty of other reasons to explore this Illinois charmer. The entire downtown is on the National Register of Historic Places. And the restaurants here serve up delicious local produce, fresh from the farms that surround the town.
A popular stop along the Ohio River Scenic Byway, Madison is a small leafy town brimming with inviting boutique stores, cosy cafes and beer gardens. Surrounded by rolling hills and stark limestone bluffs, it is packed with landmarks and museums. Echoes of the past can be seen everywhere and often in the most unlikely places, like in the hitching posts dotted around the lovely historic district (pictured). In summer, head to the award-winning wineries in the surrounding hills. Either the Lanthier or Thomas Family wineries make a great place to start.
‘Get out of Dodge’ is a common idiom for making a hasty exit and can be traced back to the 19th century when this beautiful little town was notorious for its gunfighters, gambling, brothels and saloons. You can still have a western adventure in Dodge. There are gun-fight reenactments at the Boot Hill Museum, an annual roundup rodeo in the summer and historical buildings that date from that time. But there is a sophisticated modern side too, with restaurants offering world-class cuisine and a busy cultural calendar to boot.
Gorgeous Frankenmuth was founded by Lutheran immigrants from Bavaria who set about creating a little bit of their home country in the middle of the Midwest. These days many of the gingerbread-style buildings have been turned into restaurants and shops, with beer, bratwurst, pretzels and schnitzel the order of the day. Make sure to drop by Bronner’s Christmas Wonderland, the largest Christmas store in the world and one of the few places where you can stock up on handcrafted festive decorations any time of the year.
Ely is the gateway to the Boundary Waters Canoe Area, a breathtakingly beautiful landscape of unspoiled lakes and forests, perfect for outdoor activities any time of the year. Rent a cabin in town and simply head into nature. Ely is also home to the North American Bear Center, where you can learn all about these misunderstood creatures and even meet some (open spring to autumn). Other attractions include the International Wolf Center, Arts and Heritage Center and Dorothy Molter Museum.
The tiny rural community of Lucas is known as the ‘Grassroots Art Capital of Kansas’ with many of the 400 residents busy creating quirky outsider art. There’s yard art at every turn, as well as a rock artfully placed in the middle of the road and a public toilet, covered in mosaics, that was voted the 2nd best restroom in the USA. Start at The Grassroots Arts Center for an overview of the work of local artists, drop by the World's Largest Things Museum and finish up with a plate of Czech ring bologna sausage from Brant's Meat Market, now in its third generation.
The heart of Michigan’s fabled ‘Art Coast’, charming Saugatuck is a diverse community where the good things in life are indulged and celebrated. The town is perfect for a weekend of art and epicurean adventures, bursting with galleries displaying the work of local and national artists and a foodie scene that features everything from farm-to-table eats, celeb chef-driven restaurants and coastal concepts, all with impressive wine lists, of course. End your day chilling out at gorgeous Oval Beach, your toes wiggling in the powdery sand as the sun sets.
Located on the shores of Lake Superior and tucked away in the furthest northeast corner of Minnesota, Grand Marais offers the chance to really get away from it all. Even at the height of summer you’ll feel as though you have the town all to yourself. Things do get a little busier when Grand Marais hosts one of its famous festivals like the Fisherman’s Picnic, Moose Madness and the Grand Marais Arts Festival. But head down to the town’s iconic lighthouse (pictured) by the lake to watch the sunrise or sunset and serenity is guaranteed.
Archaeological evidence shows people have been living in the area around Arrow Rock for more than 10,000 years and who can blame them? Perched on bluffs above the Missouri River, it is one of the loveliest spots in the state. The town itself was founded in 1829 as a frontier village along the Santa Fe Trail, and thanks to the non-profit organisation Friends of Arrow Rock many of the historic buildings from that time have been lovingly preserved. Pictured here is the town's beloved Lyceum Theatre, located on the site of a historic old church.
Aurora was incorporated as a village in 1877 and quickly became an oasis on Nebraska’s vast untamed plains. Historic homes still dot the town’s picturesque brick-lined streets and the imposing redbrick Hamilton County Courthouse, overlooking the town square, is a reminder of the town’s importance as an administrative centre. Head to the excellent Plainsman Museum (pictured) to learn more about this period. It includes an agricultural museum and replica 19th century schoolhouse. Kids will love the award-winning Edgerton Explorit Center, an interactive science museum that gives them the chance to learn through play.
If you love untouched nature and small, charming towns you are going to absolutely love Medora. This tiny settlement in North Dakota sits right in the middle of Theodore Roosevelt National Park and is encircled by painted canyons and vast badlands wilderness. The town itself retains many of its historical buildings, including Chateau de Mores, which belonged to the French nobleman Antoine de Vallombrosa – the Marquis de Mores and the original founder of Medora. Make sure to take in a performance at the Burning Hills Amphitheater, an open-air performance hall, nestled beside the Little Missouri River Valley. It reopens for the season in June 2024.
Just 25 miles (40km) south of St Louis, the charming town of Kimmswick makes for an unlikely tourist destination. But while the town is small – the US Census put the population at a mere 157 people in 2010 – it has a social calendar rammed with exciting events: an annual Strawberry Festival in June, a Bluegrass Festival shortly after and an Apple Butter Festival in October. The rest of the year the historic downtown is home to many homegrown boutiques, art galleries, gift shops and antique stores. The town’s two bakeries – the Dough Depot and the Blue Owl – also do a roaring trade.
Valentine in Nebraska sits just a few miles from the South Dakota border and just east of the sprawling grasslands of the Fort Niobrara National Wildlife Refuge. Its motto is ‘small town, big adventure’, a promise it delivers in abundance. Hike here and you’ll encounter elk, bison and greater prairie chicken. Nearby Smith Falls State Park is home to Nebraska’s highest waterfall. And the Cherry County Historical Society Museum preserves and celebrates the pioneer era culture of the region.
At first glance Jud appears to be like any other small rural town in North Dakota. But on closer inspection you’ll notice the murals that local residents have created over the years on the sides of barns, houses, shops and other unlikely places. Many feature rural themes (such as the one pictured), but you’ll spot murals of patriotic scenes, stamps, landscapes and even cartoon characters. Walking around here feels like visiting an outdoor art gallery.
This charming small town just east of Dayton has always been a haven for creatives, bohemians and free thinkers. It was settled around a spring said to have curative powers, and has remained an alternative hotspot. It’s the kind of place where local yarn bombers decorate trees with knitted graffiti and buskers and street performers entertain visitors who flock to the town for its colourful boutiques, galleries and cafes. Just beyond the delightful downtown you’ll find Glen Helen Nature Preserve and John Bryan State Park, perfect for getting back to nature.
Relive the days of the Wild West with a visit to this charming old gold mining town in the northern Black Hills in South Dakota. The whole town of Deadwood has been designated a National Historic Landmark, full of historic buildings that house everything from gift shops to food haunts and more. Legendary characters like Wild Bill Hickok and Calamity Jane passed through Deadwood and are remembered in the form of historical re-enactments which include shootouts on Main Street, the slaying of Hickok plus the trial of his murder.
Named after the canton of Glarus in eastern Switzerland, New Glarus was founded in the mid-1800s by Swiss migrants who set about building a home-away-from-home, complete with biscuit-tin houses, cuckoo clocks and window boxes full of geraniums. Indeed, the town is so authentically Swiss that tourists come from Switzerland to experience what the country used to be like. And yes, that is Swiss music you can hear being piped throughout downtown.
As you gaze out over Lake Erie and Sandusky Bay it is easy to understand why so many people come to this laidback lakeside town to escape the hustle and bustle of modern life. There are cute stores and bustling restaurants, of course, plus Marblehead Lighthouse (pictured), built in 1821. The Great Lakes’ oldest continuously operating lighthouse, it makes the perfect spot to contemplate life and realise it's so much better when enjoyed at a Marblehead pace.
Located in the heart of the Black Hills National Forest, Custer is one of the oldest towns in South Dakota. Its atmospheric downtown is bustling with restaurants, shops and museums, most set in historic buildings. But the town’s real charm lies in the nearby Custer State Park where wild buffalo roam and its jam-packed calendar includes an Annual Buffalo Roundup and lively Arts Festival. It's a real slice of the old Wild West.
Known as Lake Superior’s hometown, Ashland is a colourful port city with a penchant for the great outdoors and, in particular, fishing. The downtown is famous for its vibrant murals and lively bars, restaurants and cafes. But when the temperature drops, winter sport enthusiasts descend upon the town to ski, snowshoe, sled and ice fish. Snowmobilers come for the 200+ miles (322km) worth of well-kept trails in the area. Others come to visit the spectacular ice caves on Apostle Islands National Lakeshore, a short boat ride away.
Nothing says small town charm like covered bridges and this historic settlement west of the Starved Rock State Park has two of them. Princeton’s gorgeous main street has a distinctly ‘old-time’ feel, with cosy shops and antique galleries as well as cafes serving up freshly baked treats. The town is also home to the Lovejoy Homestead, a vital stop on the Underground Railroad for enslaved people escaping oppression in the south. And there are a number of scenic bike trails for those who like to get active on their weekends away.
Charming Wamego leans hard into Kansas’s links with the iconic movie, The Wizard of Oz. Many of the town’s quaint establishments (Oz Winery and Toto’s TacOZ, to name but two) have names referencing the movie and there’s a Wizard of Oz Museum, featuring artefacts from the Emerald City, that attracts fans from all over the world. Elsewhere, Wamego’s 12-acre city park features a Dutch Mill and the Historic Museum and Prairie Town Village.
Visit Mark Twain's boyhood home, take a sightseeing cruise on the Mark Twain Riverboat, then drop by the Mark Twain Cave and Cave Hollow Winery. The small Missouri town of Hannibal is very proud of its most famous son and wants to celebrate the achievements of one of America’s greatest writers with you. Wander along the riverfront and you’ll spot the landmarks that inspired his writing, as well as Jim's Journey: The Huck Finn Freedom Center, dedicated to the character of Jim from The Adventures of Huckleberry Finn, which offers an insight into the plight of African Americans in the pre-Civil War United States.
There are very few cars in this tiny village on South Bass Island in Lake Erie. Locals and vacationers alike prefer to get around using golf carts, bicycles and boats. Life here is centred on the water, from the famous Boardwalk restaurant to the secluded coves and stony beaches of South Bass Island State Park. The most striking landmark is the Perry's Victory and International Peace Memorial, a huge column commemorating the 1812 Battle of Lake Erie. The village is also home to Crystal Cave, the world's largest geode.
When explorers Captain Meriwether Lewis and Lieutenant William Clark looked out from a bluff of the Missouri River in southeastern South Dakota more than 200 years ago, they could never imagine the stately town of Vermillion that would rise on the very spot where they camped. Impressive architecture, a vibrant culture and natural beauty make for a perfect weekend break. Drop in on the National Music Museum, home to more than 15,000 musical instruments. Stroll through the grand buildings of the University of South Dakota (pictured). Or hike to the top of Spirit Mound Historic Prairie, just like Lewis and Clark did.
Settled by a progressive German religious group called the Harmonists, this tranquil town in southern Indiana has always had a laidback vibe. Its founding fathers believed in community stewardship and this is reflected to this day in the town’s architecture and planned leafy streets. Make sure to visit the town’s famous ‘roofless’ church (pictured), designed by architect Philip Johnson. He believed that the only roof large enough to encompass a world of worshippers was the sky.