17 Unique Towns to Visit on a Midwest Road Trip with Kids

A dad and his daughter sit at a picnic table enjoying lunch in Door County.
Photo Courtesy: Antonia Grant

Families looking for a unique vacation idea should consider a Midwest road trip with kids! The Midwest offers a variety of charming locations to explore and make memories together. Families will love Grand Marais, Minnesota, where you can dip your toes in Lake Superior or search for moose along the Gunflint Trail. Then, head to Galena, Illinois, which is one of the most charming Midwest towns to visit with kids! Explore the town’s many historic buildings and learn about the 1832 Black Hawk War. Or, maybe Door County is more your style? This Wisconsin peninsula is dotted with unique small towns, including one that can only be reached by ferry! Here, your family can go hiking or meander lavender fields! No matter what’s on your Midwest bucket list, you’ll find plenty to do in these 17 Unique Midwest Towns to Visit on a Midwest Road Trip with Kids!

Pro Tip: To help your planning, we’ve also included nearby cities (all 5 hours or less) to pair with these family-friendly small Midwest towns for your road trip with kids, as well as lodging options for each location.

Cedar Rapids, Iowa

A view of a museum, wiht a large lion statue in Cedar Rapids, Iowa.
Photo Courtesy: Cedar Rapids Tourism

One of the best small towns to visit in the Midwest with kids has to be Cedar Rapids, Iowa. While in Cedar Rapids, be sure to meander through the kid-friendly Cedar Rapids Museum of Art, home to the largest collection of American Gothic artist Grant Wood’s work. Up for another museum? Head to the National Czech and Slovak Museum & Library, which features interactive exhibits and heritage programs.

Then, get ready to treat the kids to a unique shopping experience. The year-round public market, NewBo City Market, is held in the center of Cedar Rapids’ New Bohemia neighborhood. Taste the local flavors of Iowa’s growing food culture, including produce and prepared food, as well as vendors who sport crafts from locals! Finally, don’t miss the many outdoor activities, including farm visits and hiking! On your Midwest road trip with kids, spend a night or two in Cedar Rapids. 

Nearby City Pairs: Chicago, IL (less than 4 hours), Minneapolis, MN (less than 4.5 hours), and Omaha, NE (less than 5 hours).

Where to Stay in Cedar Rapids with Kids

While in Cedar Rapids, you can choose from cozy B&Bs, home rentals, and full-service hotels. Firstly, Homewood Suites by Hilton Cedar Rapids-North offers suites with a fully equipped kitchen, just 10 minutes from downtown. Then, the DoubleTree by Hilton Hotel Cedar Rapids Convention Complex is just a short walk from the Cedar Rapids Museum of Art and Paramount Theatre. You’ll also find plenty of home rentals through sites like Airbnb or VRBO, as well as campgrounds and RV sites.

Top 20 Cedar Rapids house rentals from $69/night | Vrbo

Deadwood, South Dakota

When taking a Midwest road trip with kids, Deadwood, South Dakota, is a must-see! With ties to the gold rush, Deadwood is just as wild today as it was when legends like Wild Bill Hickok wandered the streets and local establishments. Not only is this one of the best-hidden gems in the Midwest, but the entire town is also a National Historic Landmark!

During your visit, wander the charming downtown area and soak in the history around every corner. Then, try your luck at the Broken Boot Gold Mine. Here, you can pan for gold after touring one of the historic mining shafts. Afterward, grab a pint at the Miner Brewing Company, where you can play lawn games or enjoy one of the concerts on the lawn. You can also check out Tatanka, where you’ll hear the Story of the Bison, as well as learn about the Lakota people.

Nearby City Pairs: Rapid City, SD (less than 1 hour), Casper, WY (less than 4 hours), and Bismark, ND (less than 5 hours).

Read Next: 5-Day Family-Friendly Itinerary For Badlands National Park

Where to Stay in Deadwood with Kids

Offering everything from hotels to cabins and camping, to B&Bs, you’ll find the perfect place to call home while staying in Deadwood. Just a few blocks from downtown, consider First Deadwood Cottages. Each cottage includes at least two bedrooms, off-street parking, and a hot tub! Nearby Hotel Alex Johnson Rapid City, Curio Collection by Hilton, provides a charming stay featuring a rooftop bar, salon, and spa. Looking for something a bit more rustic? Try the Creekside Campground, including options for cabin stays, RVs, and tent camping.

Door County, Wisconsin

A young girl stands on School House Beach in Door County on a beautiful fall day, a great stop for a Midwest road trip with kids.
Photo Courtesy: Antonia Grant

Door County is located on a peninsula in Wisconsin and offers many unique places to stay in the Midwest! With a line of charming towns dotting the western coast, you’ll find the perfect home base for your stay. Our families recommend Egg Harbor, Sister Bay, or Gibraltar. For a truly unique experience, take the ferry to Washington Island, where you can find a cozy place among the island’s lavender fields!

While visiting, check out one of Door County’s many lighthouses. Adventurous families can explore Pottawatomie Lighthouse, the oldest lighthouse on the peninsula, located in Rock Island State Park. If you time it right, you can also see the cherry blossoms or pick cherries yourself in one of the many u-pick locations. Families with diving experience can also go diving among the off-shore shipwrecks in Lake Michigan! Kayaking, hiking, and camping are additional experiences you can have here.

Nearby City Pairs: Milwaukee, WI (less than 2.5 hours), Madison, WI (less than 3.5 hours), and Chicago, IL (less than 4 hours).

RELATED: Best Places To Visit In Wisconsin For Families

Where to Stay in Door County with Kids

Door County offers many unique places to stay along the peninsula and on Washington Island. Find options for resorts, hotels, cabins and cottages, and camping. Firstly, find various accommodation options at Baileys Harbor Yacht Club Resort, nestled along the eastern coast of Door County. Plus, this waterfront resort includes over 1,000 acres ideal for hiking and snowshoeing. Alternatively, find four ways to camp in Door County, including rustic, off-the-beaten-path campsites and options for RVs.

Find Top 50 Door County waterfront vacation rentals On Vrbo.com

Galena, Illinois 

A buggie is pulled by two white horses down the main street of historic Galena, IL, a great stop for a Midwest road trip with kids.
Photo Courtesy: VisitGalena.org

Looking for one of the most family-friendly vacation destinations in the Midwest? Check out Galena, Illinois. Wander Main Street, which offers over 100 charming shops and boutiques, including fanciful candy and ice cream parlors, to treat the kids! History enthusiasts will adore Galena, as about 85% of the buildings in town are on the National Register of Historic Places.

You can learn more about local history at the Apple River Fort, which catalogs the 1832 Black Hawk War fought between settlers and the indigenous Sauk tribe. After soaking in some local history, head to Galena Cellars Vineyard and Winery for a glass of wine perfectly paired with charming country scenery (dog friendly!). Finally, adventurous kids will love Chestnut Mountain Resort, where you can select from an alpine slide, zip-lining, segway tour, and more! Families will surely find Galena one of the most unique places to visit in the Midwest!

Nearby City Pairs: Madison, WI (less than 2 hours), Chicago, IL (less than 3 hours), and Minneapolis, MN (5 hours).

Where to Stay in Galena with Kids

Charming Galena also offers historical places to lay your head after a long day, including the Hellman Guest House. Standard rooms and one suite offer stunning views of Galena and quick access to outdoor activities. Or, consider the Irish Cottage Inn & Suites, nestled among the iconic rolling hills and a quick drive from downtown Galena. Both rooms and suites are available, each offering complimentary breakfast and access to the indoor pool and hot tub.

Find Galena cottage rentals on Vrbo.com.

Grafton, Illinois 

A view of the Grafton, IL skytour overlooking the local river and fall foliage.
Photo Courtesy: Great Rivers & Routes

Nestled along the confluence of the Mississippi River and Illinois Rivers, Grafton, Illinois, is one of the hidden gems in the Midwest! Located under an hour from St. Louis, Missouri, Grafton is widely known for its sweeping scenic views and vibrant downtown area.

Outdoor enthusiasts can spend their days hiking in bluffs and wooded areas within Pere Marquette State Park. Or, rent boats and jet skis to explore Grafton Harbor by water. Brave kids will love getting a view of the rivers by air while zip-lining. The fastest run even gets up to 45 mph! After your heart resumes its normal beat, do a little window shopping as you stroll along the downtown area. You will find a wide variety of antique stores, small shops, and locally owned businesses. While exploring the riverside, stop by The Loading Dock to nibble on the catch of the day.

Continue your Midwest road trip with kids to St. Charles, Missouri, on The Grafton Ferry, operated by the Calhoun Ferry Company. Or, check out nearby Alton, Illinois, another charming Midwest town recommended by our families!

Nearby City Pairs: St. Louis, MO (less than an hour), Kansas City, MO (5 hours), Chicago (5 hours), and Indianapolis (5 hours).

Where to Stay in Grafton with Kids

Find vacation rentals, B&Bs, and cozy cabins for your stay in Grafton. Consider the Tara Point Inn & Cottages, which offers standard rooms, suites, and on-site cottages. Overlooking the Mississippi and Illinois rivers, you’ll have ample space to spread out, as well as quick access to Grafton and St. Louis. Families will also find campsites available at Pere Marquette.

Grand Marais, Minnesota

Left image: A view down the street, featuring Beth's Fudge, in Grand Marais, Minnesota. Right Image: A young girl wearing a red vest picks up stones along the Lake Superior beach in Grand Marais, Minnesota.
Left Image: Steph Eiden, Right Image: Antonia Grant

Grand Marias, Minnesota, is one of the best family-friendly vacation destinations in the Midwest. Nestled along the north shore of Lake Superior, this enchanting town has a lot to offer for all ages! Embark on a tour aboard the iconic Hjørdis for an unparalleled view of Grand Marais and Lake Superior. Or, get on the water by kayak for another unique view of the local Sawtooth Mountains.

After your tour, meander around Artist’s Point, a short hike ideal for kids. Then, adventurous children will love walking out to the Grand Marais Light House. Be sure to have shoes that can get wet! Not up for a walk? Grab a coffee from Java Moose and sit on the nearby beach while kids throw rocks into the water. Outdoor families can also find several amazing hikes, including those within Cascade River State Park (which includes a waterfall!) and Judge C.R. Magney State Park.

Nearby City Pairs: Thunder Bay, Ontario (90 minutes, plus boarding crossing), Duluth, MN (2 hours), and Minneapolis, MN (4.5 hours).

READ NEXT: 31+ Amazing Places To Visit In Northern Minnesota With Kids

Where to Stay in Grand Marais with Kids

Various fantastic accommodation options along the North Shore offer quick access to Grand Marais and outdoor adventures. In town, consider Grand Marais Campground and Marina, featuring cobblestone beaches and on-site mini-golf within walking distance to downtown. Offering suites and dog-friendly accommodations, East Bay Suites is nestled along the edge of Lake Superior in the heart of Grand Marais. Finally, 8 miles outside of Grand Marais and near the Gunflint Trail, families will love Skyport Lodge. Offering both lodge-style rooms and cabins, Skyport Lodge is situated among the pines and offers picturesque views of Devil Track Lake.

Book Lake Superior Beachfront in Grand Marais on Vrbo

Hannibal, Missouri

Two costumed locals look at the Mark Twain River Boat in Hannibal, MO.
Photo Courtesy: Visit Hannibal MO

Headed to Missouri on your Midwest road trip with kids? Be sure to check out Hannibal! Under two hours from St. Louis, Hannibal is one of the most unique places to stay in the Midwest, especially for literary enthusiasts.

Children familiar with the tales of Huck Finn and Tom Sawyer will delight in visiting the boyhood home of Mark Twain. Here, learn how Mark Twain turned childhood friends into beloved storybook characters! Have a family member interested in Titanic history too? Unsinkable Molly Brown’s birthplace and museum are also found in Hannibal. Once you’ve had enough historical tours, head to the Mark Twain Cave Complex, featured in several of Mark Twain’s novels. Kids will love exploring the caves by lantern light!

Nearby City Pairs: St. Louis, MO (2 hours), Kansas City, MO (less than 3.5 hours), and Chicago, IL (less than 5 hours).

Where to Stay in Hannibal with Kids

Find hotels, B&Bs, and campgrounds to suit your stay in Hannibal with kids. Families looking for a hotel stay can find rooms and suites at Holiday Inn Express & Suites Hannibal – Medical Center. Just off Interstate 36, you’ll find this hotel convenient to all major area attractions. Or, consider a more intimate stay at the Dubach Inn Bed & Breakfast, offering several suite options, which include private baths and private sitting rooms. Located in the historic district of Hannibal, the Dubach Inn Bed & Breakfast is just a few blocks from Hannibal’s best shops, museums, and more! Finally, camping is seasonally available at the Mark Twain Cave Campgrounds.

Holland, Michigan

A colorful garden in Holland, Michigan, featuring a gazebo, flags. and a windmill.
Photo Courtesy: Discover Holland

Families looking for one of the best-hidden gems in the Midwest will adore Holland, Michigan. With an award-winning downtown area, you can shop until you drop, no matter the season (there are heated streets in the colder months!).

Time your family trip right, and you can attend the world-renowned Tulip Time Festival. Kids will love finding tulips in all of their favorite colors! In line with the Dutch theme, be sure to check out Dutch Village. This family-friendly attraction features a small theme park, Dutch-inspired crafts, and tasty foods to thrill the whole family! Families seeking outdoor adventures won’t be disappointed either. You can try everything from sailing Lake Michigan to hiking wooded trails and more! In fact, you can even find sandy beaches to lounge on during the summer months. Encounter a rainy day? Check out BAM! Entertainment Center, which offers everything from escape rooms to bowling alleys!

Nearby City Pairs: Chicago, IL (2.5 hours), Indianapolis, IL (just over 4 hours), and Milwaukee, WI (less than 5 hours).

Where to Stay in Holland with Kids

In Holland, find everything from hotels to cottage rentals and campgrounds. Stay downtown at the CityFlatsHotel for a convenient hotel location. Or, consider Home2 Suites by Hilton Holland to ensure you have room to spread out. Then, Teerman Lofts offers luxury suites in one of Holland’s most historic buildings. Families will also love the outdoor pool and boutique resort experience at The Beach House At Lake Street. Just a short drive from downtown, The Beach House At Lake Street is nestled in the lakeshore area, across the street from Lake Macatawa, and a short walk from Lake Michigan. Finally, Holland State Park offers family-friendly campsites, as well as sugar sand beaches, and a bounty of outdoor adventures!

RELATED: 45 Fun Places To Visit In Michigan’s Lower Peninsula With Kids

Mackinac Island, Michigan

A young girl and her father bike along a charming, tree-lined streen on Mackinac Island, Michigan, a great stop for a Midwest road trip with kids.
Photo Courtesy: Cali McKenney

One of the most unique places to visit in the Midwest is a Michigan island offering enchanting strolls, bike rides, and horse-drawn carriage tours. Ditch the car on this stop of your Midwest road trip with kids; Mackinac Island is a no-vehicle island that allows families to unwind and connect in magical ways, starting with the ferry ride from Mackinaw City or St. Ignace.

Begin your family vacation in Mackinac Island by hailing a horse-drawn carriage to survey the charming downtown area. Afterward, stop at the many fudge shops in town for a taste of what makes Mackinac Island so special. Then, head to the iconic Arch Rock. Pack a picnic lunch and make it a truly memorable day! Adventurous families can also explore the island by kayaking, parasailing, sailing on Lake Michigan, or aboard a fishing charter. Finally, pack your clubs; there are three golf courses on the island!

Nearby City Pairs: Marquette, MI (3 hours, plus ferry time from the island), Grand Rapids, MI (less than 4 hours, plus ferry time from the island), and Detroit, MI (less than 4.5 hours, plus ferry time from the island).

Where to Stay on Mackinac Island with Kids

No matter what your lodging preferences are, you’ll find what you’re looking for on Mackinac Island. From resorts to cottages to condos and more, Mackinac Island has it all! When staying in Mackinac Island, our families recommend the Grand Hotel for those looking for an elegant afternoon tea, access to horse-drawn carriage rides, and posh dinners to orchestral music. Need something less formal? Consider The Inn at Stonecliffe, which offers quiet tranquility away from the hustle and bustle of this historic downtown area. Finally, head to Mission Point Resort for a waterfront property offering standard rooms and suites, as well as an array of family-friendly activities on-site. Plus, kids eat free and can indulge in one of the many complimentary kid’s activities!

Book Hotels in Mackinac Island State Park, MI

Madeline Island, Wisconsin

A series of colorful kayak rest on a beach on Madeline Island, a great stop for a Midwest road trip with kids.
Photo Courtesy: Madeline Island Chamber

If you’re looking for one of the most unique places to stay in the Midwest, you’ll want to check out Madeline Island. Located on Lake Superior, this Wisconsin island is the largest of the 22 Apostle Islands. Take the ferry from Bayfield to reach one of the best small towns to visit in the Midwest with kids!

An outdoor enthusiast’s paradise, you can hike, bike, kayak, swim, and canoe your way across Madeline Island. Families will find cozy cottages and camping sites dotting the coastline, offering picturesque views of Lake Superior and easy access to the island’s many attractions. If you encounter poor weather, head to the Madeline Island Museum. Here, you’ll discover many exhibits highlighting the island’s rich history. Or, head to Woods Hall, where kids can watch in wonder as weavers work the loom. Lucky kids may even get a chance to try it!

Nearby City Pairs: Duluth, MN (less than 3 hours) and Minneapolis, MN (5 hours).

Where to Stay on Madeline Island with Kids

When exploring Madeline Island, you can opt to stay on the mainland or the island. On the island, find an array of cabins, cottages, hotels, and camping options. Firstly, The Inn on Madeline Island offers cottages and condos for families, including lakefront options. Then, Ferry Landing Suites on Madeline Island gives families a taste of tranquillity and peace, as well as stunning scenery and cabin living near the island’s attractions. Finally, go rustic and camp at Big Bay State Park. Outdoorsy families will adore the 1.5-mile stretch of beach and over seven miles of hiking, boardwalk, and nature trails to explore.

Medora, North Dakota

Families looking for family-friendly vacation destinations in the Midwest will adore Medora, North Dakota! This charming town is the gateway to Theodore Roosevelt National Park, where your family can enjoy a plethora of outdoor activities. Hike among the North Dakota Badlands, where you can catch a glimpse of the roaming bison and elk. Then, enjoy the panoramic views from the Painted Canyon Overlook.

In town, put on your best cowboy boots and grab your seats for the Medora Musical, the “rootin’-tootinest” show in the Midwest. Or, head to Little Bully Pulpit for a rousing round of mini-golf. There is even a zip-line for adventurous kids. After a long day of hiking, head to the Medora Children’s Park. This free attraction is styled after the Old West and allows kids to run, climb, and play to their heart’s content! 

Finally, if you’re planning a Midwest road trip with kids to Yellowstone National Park, Medora offers an exciting overnight or two on your way! Don’t forget about the 4th-Grade National Park Pass, here’s what you need to know!

Nearby City Pairs: Bismarck, ND (2 hours), Rapid City, SD (less than 4 hours), and Billings, MT (just over 4 hours).

Where to Stay in Medora with Kids

Families will love the Western charm of the Rough Riders Hotel. Here, you’ll have the option of standard hotel rooms and suites, plus it’s centrally located in Medora. Families preferring to camp will find options for that too! In fact, you can camp along the Little Missouri River with stunning views of the North Dakota Badlands (rustic campsites and RV options are both available).

Book Your Hotel in Medora – Wonder Now, Wander Later

Mitchell, South Dakota

A large plastic ear of corn smiles near the entrance of the World's Only Corn Palace in Mitchell, South Dakota, a great stop for a Midwest road trip with kids.
Photo Courtesy: Visit Mitchell!

Next on our list of best small towns to visit in the Midwest with kids is Mitchell, South Dakota. This darling Midwest town is known for the world’s only Corn Palace, as well as offering a great location for outdoor adventures.

Families can fill their itinerary with hiking, biking, fishing, boating, and camping. In fact, Kiwanis Woodlot Park offers 8 miles of lakeshore off-road hiking and biking trails! Approximately half a million people visit the Corn Palace each year. Here, kids can explore seven quirky corn murals made out of a variety of corn types. Not to mention, admission to one of the most unique places to visit in the Midwest is free! Hunting and wildlife enthusiasts will appreciate visiting Cabela’s. Here, families can meander through museum-quality animal displays in recreations of their natural habitats, as well as huge aquariums. Plus, stock up on supplies for future outdoor adventures.

Nearby City Pairs: Sioux Falls, SD (less than 90 minutes), Omaha, NE (less than 4 hours), and Minneapolis, MN (less than 5 hours).

Where to Stay in Mitchell with Kids

Families visiting Mitchell will find a plethora of accommodation options, including everything from a Holiday Inn Express & Suites Mitchell to campsites. Those interested in camping should consider Dakota Campground, which includes options for camping, RVing, and cabin stays. If you’re looking for one of the most unique places to stay in the Midwest, check out Hetland’s Hunting Haven. Located about 20 miles outside of Mitchell, this family-owned Pheasant Hunting operation and lodge is also a working farm.

RELATED: 16 Fantastic Places To Visit In Michigan’s Upper Peninsula With Kids

Munising, Michigan

Headed to Michigan’s Upper Peninsula (UP)? Munising, Michigan, offers an ideal location for a pitstop or end destination on your Midwest road trip with kids. Nestled along Lake Superior, you’ll find plenty of outdoor adventures here. Not only are you within a short distance of Pictured Rocks National Lakeshore, featuring one of the UP’s iconic landmarks, but you’ll also be able to explore Grand Island National Recreational Area (only .5 miles offshore!).

Hike about Pictured Rocks National Lakeshore to see Miners Castle, and, further along, the shore, Sable Falls. You can even take a Glass Bottom Shipwreck Tours. Kids will delight in seeing several shipwrecks up close. Afterward, explore the water by sea kayak, or land by horseback riding or mountain biking. Within an hour, you can also reach Kitch-iti-kipi and Presque Isle Park. One thing is certain, you’ll find ample fresh air and outdoor adventures while exploring Michigan’s UP.

Nearby City Pairs: Marquette, MI (45 minutes), Green Bay, WI (just over 3 hours), and Milwaukee, WI (5 hours).

READ NEXT: The Best Upper Peninsula Michigan Hikes For Families

Where to Stay in Munising with Kids

Families staying in Munising will find an array of options in this small Midwestern town. Firstly, consider AmericInn by Wyndham Wetmore Munising, featuring an indoor pool and waterslide, as well as a complimentary breakfast. Outdoor enthusiasts will love Northwoods Resort, offering cabins and cottages located on the sandy north-shore of Au Train Lake (just 15 minutes from downtown Munising). Families will also find a variety of campgrounds, as well as home rentals, through sites like Airbnb and VRBO. In fact, Paddler’s Village offers family-friendly glamping in yurts, safari tents, and other options! 

Book a hotel near Pictured Rocks National Lakeshore, Michigan

Nashville, Indiana

Two women stand on a platform overlooking a huge forrest of green trees in Brown County.
Photo Courtesy: I Love Brown County

If you’re looking for hidden gems in the Midwest, you’ll want to visit Nashville, Indiana. Located in Brown County, Nashville offers rolling hills, meadows, and wooded areas waiting to welcome you and your family!

Older kids will love playing a round of disc golf on a championship course at the Brown County Country Club. Or, enjoy the scenery on horseback. Brown County Saddle Barn offers trail rides ideal for adventurous families. Select from two tour types, a 35-minute tour, and a 60-minute tour. Outdoor kids will adore hiking along at Brown County State Park. With nearly 16,000 acres of rugged hills, ridges, and ravines, kids and adults alike will enjoy the sights and sounds of these natural lands. Challenge teens to the Seven Visita Challenge, a social media campaign offered by Brown County State Park. In town, soak in some music history at Bill Monroe’s Bluegrass Hall of Fame Museum.

Nearby City Pairs: Indianapolis, IN (1 hour), Colombus, OH (3.5 hours), and Chicago (4.5 hours).

Where to Stay in Nashville with Kids

Offering everything from B&Bs to hotels to camping, your family will find the perfect home base for your outdoor adventures in Nashville, Indiana. Stay inside Brown County State Park at Abe Martin Lodge and Cabins, offering a cozy cabin experience. Then, Artists Colony Inn offers a centrally located stay downtown with breakfast included. The offers standard rooms, as well as three suites. Finally, those looking for a rustic camping experience will delight in staying at Camp Palawopec. Here, book a small open-air cabin with quick access to fishing, canoeing and kayaking, swimming, hiking, and more!

Top Hotels in Nashville, IN from $87 | Expedia – expedia.com

Shipshewana, Indiana

A large white building, featuring a colorful quilt sqaure, stands proudly surrounded by blooming trees on a sunny day in Shipshewana, a great stop for a Midwest road trip with kids.
Photo Courtesy: Visit Shipshewana

If your Midwest road trip with kids brings you through Indiana, don’t miss visiting Shipshewana. Here, you’ll experience the simplicity of Amish culture, as well as explore the great outdoors! Learn more about Amish culture with a tour from Buggy Lane Tours, where you can book anything from a short buggy ride through the countryside to tours of real working Amish farms.

Or, check out Dutch Creek Farm Animal Park, offering seasonal opportunities to meet and feed the animals. Located just 10 minutes from town, kids will adore this safari-style wagon ride and an animal encounter. Afterward, practice your mini-putt at Shipshe Pizza & Mini-Golf, a local favorite. Finally, a visit to Shipshewana isn’t complete without soaking in the sights, sounds, and busy activity of Shipshewana Trading Place Flea Market. As the largest flea market in the Midwest, it offers everything from fresh produce to art to crafts and antiques.

Nearby City Pairs: Chicago, IL (less than 2.5 hours), Indianapolis, IN (3 hours), and Colombus, OH (less than 4 hours).

Where to Stay in Shipshewana with Kids

Staying overnight in Shipshewana? You won’t be disappointed in your options! Families will find choices for hotels, cabins, camping, and more. Those needing a standard hotel stay will find everything they need from Van Buren Hotel At Shipshewana, including a fitness center, indoor pool, and complimentary refreshments. Or, check out Shipshewana North Park Amish Log Cabin Lodging & Campground for cabin and camping options. There is even a frozen custard stand on the property! Finally, Shipshewana Campground South Park is another option that allows camping and RV stays.

Shipshewana Auction and Flea Market vacation rentals.

Ste. Genevieve, Missouri

A series of parade walkers wander down a street, featuring men in colonial costumes and children carrying flags in Ste. Genevieve, a great stop for a Midwest road trip with kids.
Photo Courtesy: VisitSteGen

If you’re looking for unique places to visit in the Midwest featuring local wineries and craft beer, Ste. Genevieve, Missouri, is the place to be. In fact, Ste. Genevieve has an impressive history of winemaking, starting with their early French settlers.

You’ll find over a dozen wineries and breweries waiting to welcome you with glass in hand. From mom-and-pop wineries to the handcrafted beers and distillery of Crown Valley Brewing and Distilling, you’ll find the ideal place to toast your family. Then visit Baetje Farms, where kids can feed resident goats, while parents try farm-made artisanal cheese. As one of the best small towns to visit in the Midwest with kids, you won’t want to miss the Linden House, providing educational French Colonial Activities for the whole family. Finally, find endless fun on the water slides, lazy river, and zip-line at River Rapids Water Park!

Nearby City Pairs: St. Louis, MO (1 hour), Kansas City, MO (4.5 hours), and Indianapolis, IN (less than 5 hours).

Where to Stay in Ste. Genevieve with Kids

Find everything from hotels to B&Bs to family-friendly Airbnbs in Ste. Genevieve. Firstly, Hotel Audubon Grill & Bar offers a centrally located stay in the historic downtown area. You’ll even find a family-friendly chef-crafted menu and private dining options here. Those looking for a cozy B&B stay will adore Main Street Inn. With standard rooms and suites, you’ll find the ideal space for your stay. Finally, find an array of delightful Airbnbs in Ste. Genevieve, including Ms. Bettes Place.

Stillwater, Minnesota

Families looking for family-friendly vacation destinations in the Midwest will adore Stillwater, Minnesota. Nestled along the St. Croix River with quick access to the Twin Cities, kids will delight in exploring this historic town, offering everything from authentic paddlewheel riverboat tours to gondola rides. Stillwater is an ideal Midwest location for outdoor adventures, historical tours, and making memories.

Begin your stay with a 45-minute narrated Stillwater Trolley, where knowledgeable guides share local tales and lore. Then, walk across the historic lift bridge into Wisconsin. If you loved the view from the bridge, you’ll love the view from the water even more! Take a paddlewheel riverboat with Stillwater River Boats, offering public cruises and private charters. Need a new perspective? Rise into the air with a whimsical hot air balloon ride over Stillwater. Finally, your family can also explore the great outdoors in Stillwater by foot, bike, pontoon, or horseback.

Nearby City Pairs: St. Paul, MN (less than 30 minutes), Minneapolis, MN (30 Minutes), and Iowa City, IA (less than 5 hours).

Where to Stay in Stillwater with Kids

If your Midwest road trip with kids is headed to Minnesota, Stillwater is a great home base! Find comfort and luxury at Hotel Crosby. Located in the heart of downtown Stillwater, this hotel offers cozy rooms and suites, as well as a roof-top hot tub and on-site spa. Looking for a historic stay? Located on the Historic Registry, the Lowell Inn has been in operation since 1927 and offers an array of rooms and suites and fine dining options. Finally, get cozy at the Aurora Staples Inn. Just three blocks from downtown, this B&B provides Victorian-style rooms and suites.

Top 50 Stillwater Vacation Rentals | Vrbo.com

Happy Traveling!

Little girl on a pebble beach of Lake Superior in Grand Marais, Minnesota, a great stop for a Midwest road trip with kids.
Photo Courtesy: Antonia Grant
Grand Marais, Minnesota

We’re confident you found an amazing town or two on this list to visit on your Midwest road trip with kids. With so many family-friendly vacation destinations in the Midwest, narrowing down your options will be the hardest part of your vacation planning (which is why we compiled this list!). Outdoor adventures, historical tours, charming wineries, and more await you and your family on your family road trip. From Lake Superior to southern Illinois, there are so many amazing places to explore and make memories with your kids. Now, you just have to decide where you’re going to go! Happy traveling!

*Due to the COVID-19 pandemic, some of the places on this list may have reduced services or may temporarily close at times. Please ensure availability before making your decision.

*This post may contain affiliate links that may earn us a small commission, at no additional cost to you. Affiliate links in no way inform the hotels, sights, products, or other recommendations included in our articles. All opinions and recommendations expressed here are compiled from submissions submitted by the generous members of our Families Who Love To Travel community.


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Fantastic Things to Do in Kauai with Young Kids

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The Families Love Travel Team has a zest for life and an even bigger passion for globetrotting! Comprised of real-life travel professionals, we work hard behind the scenes to provide dynamic solutions for adventuring with children. Our enthusiastic team understands the challenges that often accompany traveling with kids and is committed to making Families Love Travel an inclusive space to convey these experiences.