K.C. was a featured writer for Yahoo! Travel before joining trips to discover in 2013. She is the author of Best Travel Guide for First Time Visitors to Ireland, an Amazon bestseller every year between 2013 and 2016. She has been a featured expert on Newsweek, Travel + Leisure, Travelocity, among others.
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While the Midwest may not often get the spotlight, there are many charming small towns and family-friendly vacation destinations throughout the area that are well worth a visit. You might be surprised to find everything from sparkling lakes, forested mountains, and white sandy beaches to fall foliage so stunning it could easily give New England a run for its money. These destinations in particular provide a fabulous escape from the hustle and bustle, with plenty of attractions to keep you busy.
Located in Michigan’s Upper Peninsula, Marquette has a rich history and picturesque downtown, but the biggest draw is its scenery and outdoor adventure. There are many pretty lighthouses throughout the area and it’s surrounded by 300 miles of forest, cascading waterfalls, and miles and miles of trails for hiking and biking. The Harlow Lake Recreational Area offers both with a postcard-perfect lake view. While it’s gorgeous year-round, it’s a popular Midwest destination in autumn with a blanket of vibrant gold, orange, and red hues.
Take a trip back in time by visiting Galena with historic buildings that date from the pre-Civil War era. A popular weekend getaway in Illinois, it was once home to President Ulysses S. Grant and offers lots when it comes to history, including museums to explore and even ghost tours with some of its residents from the past still lingering. Nestled among scenic hills there are plenty of parks and recreational activities to enjoy too. After all your exploration, you might want to go for a winery or distillery tasting.
Deadwood is a fun place to relive the days of the Wild West, a destination many people are familiar with thanks to the HBO series with the same name. In the 1870s thousands were drawn here with the hopes of striking it rich or making money off those who did. Wild Bill Hickok was one of them, famously shot in the back during a poker game in the summer of ’76. In 1989, legalized gambling returned, transforming the town into a popular destination for tourists with a wide range of attractions to explore. You can pan for gold, watch a shootout reenactment on Main Street, and tour the magnificent Mount Adams House, a Queen Anne-style mansion turned museum. After dark, enjoy all sorts of entertainment, including live music.
Located where the majestic Badlands meet the Great Plains, Medora is the gateway to Theodore Roosevelt National Park known for its painted canyons and serene prairies where Roosevelt loved to visit. The popular town in North Dakota offers many of the same highlights the park features, providing the perfect base. Watch for the many bison and prairie dogs, hike, horseback ride, or whiz across a zipline. When it’s time to fuel up, don’t miss the interactive Pitchfork Steak Fondue dining experience.
A hidden gem with an 11-block downtown area filled with 19th-century buildings on the National Register of Historic District, there’s lots to love about Winona. Known as America’s stained glass capital, it’s fun to wander, with the Winona National Bank and its stunning stained glass as well as the impressive Polish-designed Basilica of St. Stanislaus Kostka. Visitors can view the town from the water on a river cruise, or paddle around Lake Winona in a kayak or canoe. Lake Park, the city park that surrounds it, has a beach, disc golf course, walking and biking trails, and a rose garden.
Located about midway between St. Louis and Kansas City, Boonville is often found on lists of the best small towns to visit, including a ranking by Smithsonian magazine. Katy Trail State Park runs through it and there are 450 sites to explore on the National Registry of Historic Places. Check out the Old Jail and Hanging Barn, the Hain House, and Roslyn Heights Mansion. You can also golf at the Hail Ridge course and explore the Mitchell Antique Motor Car Museum.
Set along the Saint Croix National Scenic Riverway, Osceola is best known for its falls, with Cascade Falls located in the heart of the town. It’s the reason it exists, used to support Osceola’s mill and brewery. It was first settled in 1844, with the downtown buildings dating back to 1880 providing plenty of charm, along with fun shops to browse. Visitors can also embark on a historic train ride with the Osceola & St. Crois Valley Railway which features vintage cars that travel for 20 miles along the sandstone bluffs of the St. Croix River.
Copper Harbor sits at the northern tip of the Keweenaw Peninsula, a stunning region with endless forests surrounded by the brilliant blue of Lake Superior. It was named for the area’s rich history of copper mining which is said to date back to ancient people seven thousand years ago. Today it’s a fabulous spot for those who enjoy breathtaking scenery and outdoor adventure with opportunities for hiking, mountain biking, water sports, and much more. It’s also the gateway to Isle Royale National Park, with ferries departing from here.
The charming town of Wamego may be small but it’s jam-packed with attractions. One of the best destinations in Kansas, it’s biggest draw is the Oz Museum which displays one of the world’s largest private memorabilia collections from 1939’s “The Wizard of Oz.” It also includes items from earlier silent film versions of the book and the chance to taste award-winning wines with names inspired by the musical at the nearby Oz Winery tasting room. Visitors can also check out the 1895 Columbian Theatre, which dates back to 1895, a beautiful city park with a Dutch Mill, the Wamego Historical Society & Museum, and Prairie Town Village.
The town of Lake Geneva is just 80 miles northwest of Chicago’s Loop, offering a wilderness getaway within easy reach. Home to Lake Geneva, visitors can stroll the 21-mile path along the lakeshore or take a boat tour for a perspective of the beauty of the water. It’s especially stunning in the fall, renowned for its brilliant foliage along with activities like apple and pumpkin picking, and corn mazes. In town, you’ll find plenty of outstanding places to dine, shop, and relax, with stress-melting spas offering massages and other treatments.
Established in 1879 as a spa town, Eureka Springs is tucked into the Ozarks as one of its prettiest towns, nestled in the hillsides while surrounded by over 60 natural springs, perfect for a relaxing soak. The winding streets in the historic downtown district are filled with gorgeous Victorian-era buildings and visitors can explore more than 100 shops and galleries too. A host of other attractions can be enjoyed like rides on an old-fashioned steam train or whizzing across a zip-line on a two-hour tour through the forest. In the evening, there are plays to catch and often live music to enjoy.
Located at the end of North Shore Scenic Drive along Lake Superior, the town of Grand Marais is overflowing with charms. Once named America’s coolest small town by Budget Travel, noting its close proximity to recreational activities and the annual Fisherman’s Picnic that celebrates its logging and fishing history with a feast along the shore, visitors will find plenty to do indoors or out. There are art galleries, independents shops, some quirky eateries, and a variety of accommodation options. It also happens to be a gateway to the Boundary Waters Canoe Area Wilderness. And in July, you can watch the annual Dragon Boat Festival where dragon-shaped boats race each other on the lake.
Chagrin Falls is named for the cascades that flow right through the center of its historic downtown. Located about 40 minutes from Cleveland it’s popular for shopping with antique stores, boutiques, and art galleries. The village still resembles the paintings of Norman Rockwell and everything is within walking distance. It hosts several popular art festivals like the Blossom Time Festival, Art by the Falls, and weekly summer concerts in the park. Don’t miss a visit to the Chagrin Falls Popcorn Shop, it’s been sitting next to the falls for nearly 75 years selling 16 flavors of popcorn, doughnuts, ice cream, and much more.
Tucked into the heart of Amish Country in Indiana, Shipshewana is a great place to learn more about Amish communities. It’s home to a museum dedicated to the Amish and Mennonites, and historic buildings that now serve as restaurants for dining on Amish dishes, aromatic bakeries, craft shops, furniture workshops, and art galleries. Visitors can enjoy buggy rides to get a feel for Amish life and on a Tuesday or Wednesday, May through September, attend the largest flea market in the Midwest. Unlike most, you’ll find some fabulous locally made artisan items here.
New Glarus is referred to as “America’s Little Switzerland,” with old-world charm, picturesque Alpine-style architecture, and flower-filled window boxes. Originally settled by the Swiss in the mid-19th-century, you’ll even hear Swiss music piped downtown. Learn more with a visit to the Swiss Historical Village Museum. There’s lots of delicious eats and drinks, including the New Glarus Brewing Company, an iconic landmark here for almost 30 years. You can take a tour and enjoy a sample too. Enjoy fudge and more than 100 cheeses at Maple Leaf Cheese & Chocolate Haus and Swiss delicacies at New Glarus Bakery which opened its doors in 1910.