Cool Cities and Small Towns To Visit in the Midwest

Travel, as we know, is changing due to the ongoing pandemic and spread of COVID-19. Travel plans and vacations have drastically altered and have many of us reconsidering our next destinations. The E.U. and even some states are implementing more robust policies when it comes to leisure travel. With these changes taking place rapidly, it is time to consider alternatives to far fetched destinations and instead recludes to regional havens in small towns and cool cities in the Midwest.

The Best Cool Cities and Small Towns to Visit in the Midwest

I am an Ohio girl and was ecstatic to create this list! But, there are so many parts of the Midwest that I am unfamiliar with, so I enlisted some more experts to help me out and create a list of the coolest small towns to visit in the Midwest. When planning your next vacation, be sure to consider any of these cool small towns as a part of your travel plans. (Note: Some of the below destinations may be affected by the coronavirus outbreak. Check with the CDC and the U.S. Department of State before traveling).

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Illinois | Indiana | Iowa | Kansas | Michigan | Minnesota | Ohio | Wisconsin


Illinois

Casey, ILLINOIS – POPULATION 2,635

Casey, Illinois, is a small town just off of I-70 between St Louis, Missouri, and Indianapolis, Indiana. This small town has a motto of “Small Town Big Things,” and they certainly live up to that motto. Casey is home to eight attractions certified by Guinness World Records as the largest in the world. If you are a roadside oddity fan and appreciate unique road trip attractions, you will undoubtedly want to take a road trip to Casey, Illinois.

Giant Pitchfork in Casey, Illinois. As featured in The Best Small Towns and Cities to Visit in the Midwest by The Haute Seeker
Giant Pitch Fork | Image by Tiffany

Do: You will find several large and even world record attractions here. Well, known attractions include the World’s Largest Mailbox, Wind Chime, Golf Tee, and so many more. 

Dine: Looking for a farm to table place to eat? Check out Richards Farm Restaurant located right next to the World’s Largest Pitchfork.

Shop: To get around Casey, IL, it is best to pick up a golf cart from the local corner store. After you do, don’t miss stopping in all the boutique mom and pop shops along the main street.

Stay: The Eighteen-Ninety is a boutique hotel that is highly recommended if you plan on staying over in this city of the “world’s largest things.”

Recommended by Tiffany of Mommy and Me Travels

Galena, Illinois – POPULATION 3,183

Galena, Illinois is a popular small town in the Midwest town. This very cool and historic city is only 3 hours away from Chicago, making it the perfect escape from the big city. If you are looking for a destination that is only a short drive away, consider this cool city.

Downtown in Galena, Illinois. As featured in The Best Small Towns and Cities to Visit in the Midwest by The Haute Seeker
Downtown Galena | Image by Kylie Nehaus

Do: For those that are interested in history, in Galena, you’ll find the former home of President Ulysses S. Grant. The home is open for guided tours. If you are interested in art, check out the West Street Sculpture Park. Visitors who appreciate the outdoors and adventure will love Chestnut Mountain Resort. In the winter this is a ski resort, but during the summer there is a zip line ride, Segway tours, and an alpine slide! It offers incredible views across the Mississippi River.

Dine: Find good eats and great brews at spots like Blaum Bros Distillery, Log Cabin, and Gobbie’s Sports Pub and Eatery.

Shop: The Main Street of Galena is half-mile of little independent businesses. You can park up at one end and then walk the length hopping between each of the stores.

Stay: Eagle Ridge Resort and Spa is a large hotel with a golf course. They hold various annual events such as the Great Galena Balloon Race (hot air balloons) and a Winter Carnival.

Recommended by Kylie Nehaus between England and Iowa

Indiana

Chesterton, Indiana – POPULATION 13,833

Not all small towns can boast the cool amount of things to do in Chesterton, Indiana. The town of Chesterton is located about 50 miles southeast of Chicago, close to the southern shore of Lake Michigan and Indiana Dunes. This small town is 15 miles away from the Indiana Dunes National Park which is full of beaches and trails.

Indiana Dune in Chesterton, Indiana. As featured in The Best Small Towns and Cities to Visit in the Midwest by The Haute Seeker
Indiana Dunes | Image by Flo Lawnicki

Do: The Indiana Dunes State Park within the National Park’s boundaries is easily accessible and offers hiking trails of various difficulty, a beach with plenty of public parking, a nature center, and tall sand dunes for climbing, leading incredibly scenic views. If you are feeling energetic, take on the 3 Dune Challenge, where you tackle the tallest dunes in the park!

Dine: For flavorful eats, check out Third Coast Café, Ivy’s Bohemian House, and Octave Grill. You must also stop in at Running Vines for a wine tasting. They host some cool events there.

Shop: Shoppers will enjoy the eclectic mix of stores and boutiques in the downtown area and the famous European Market, which runs every Saturday from May until October. 

Stay: If you are staying overnight camping amongst the scenic beauty of the Dunes is an option. Also, Riley’s Railhouse Bed and Breakfast offer a unique train-themed stay. The accommodations are in a renovated train depot! Dunes Walk Inn is also another great choice. The boutique hotel is in a renovated mansion! Or if you prefer to be nestled in the woods surrounded by nature, check out At Home in the Woods Bed and Breakfast.

Recommended by Flo Lawnickiof Flo’s Favorites

Hendricks County, Indiana – Combined POPULATION 107,311

Hendricks County, Indiana, is a blend of three small towns and cool cities in Indiana. These cities (Avon, Danville, and Plainfield). Hendricks County offers a wide array of unique attractions that attract visitors from all over the world. Located west of Indianapolis, Hendricks County boasts historic main streets, mom and pop restaurants, and plenty of family-friendly adventure. Pack your bags and your loved ones, for a family vacation to this small town in Indiana.

Lucas Oil Raceway | Image Stephanie

Do: The Lucas Oil Raceway offers up tons of thrills from getting behind the wheel of a race car to experiencing the premier drag racing event of the year, the Nationals.  Other popular attractions include the Enchanted Fairy Trail, Beasley’s Orchard, Splash Island, and more. 

Dine: A visit to the famous Mayberry Cafe is a must, a nostalgic diner seemingly out of the Andy Griffith Show. Dine on homemade classics while feeling like Barney Fife may sit down next to you at any moment. Another popular nostalgic spot is the classic retro Oasis Diner. They’ve been serving up diner favorites for decades. Be sure to venture into a few of the bakeries scattered around town. The fresh-made pastries are divine. 

Shop: Who North America is the only dedicated retailer to the longest-running science fiction show, Doctor Who! They are also home to an impressive museum full of rare and unique memorabilia. 

Stay: Staybridge Suites is the ideal spot to stay during your visit to Hendricks County. One and two-bedroom suites are available with tons of family-friendly amenities such as a pool, laundry facilities, and breakfast. 

Recommended by Stephanie at Consistently Curious

Rising Sun, Indiana (Ohio County) – Population 5,875

Located along the scenic Ohio River, the City of Rising Sun is the county seat of Ohio County, Indiana. In the 1830s, the small town was a seasonal stop for hundreds of flatboats heading down the river as well as a popular destination for powerboat racing. The quaint riverside community features local shops, eateries, and attractions—making it a charming small town destination that all will enjoy.

Music on Main. Rising Sun, Indiana. As featured in The Best Small Towns and Cities to Visit in the Midwest by The Haute Seeker
sicsMusic on Main | Image by Kendal Miller

Do: Answer the “call of the wild” with a visit to Red Wolf Sanctuary and Wildlife Rehabilitation Center. You can also book a walking tour of local cemeteries and Underground Railroad sites, browse the historic gems inside the Ohio County Historical Museum or try specialty wines at Fiekerts Homestead Wines tasting room.

Dine: Enjoy a meal outside by the Ohio River waterfront with local dining options. Try authentic Mexican cuisine from Tequila’s Mexican Restaurant or cheeseburgers from Paddy’s Wagon’s food trailer. If you are looking for all-day breakfast options, visit Jack’s Place and Main Street Diner. Have a sweet tooth? Get it fixed with treats from Blend on Main or Vintage Scoops. For late-night entertainment and drinks, visit Rockies Bar & Grill for adult beverages, pool tables, and live bands. 

Shop: Browse charming vintage treasures inside Amber’s Antiques and Flowers by Vicki and Antiques. Just a few minutes from downtown is Family Traditions, featuring new and vintage items for any décor.

Stay: Local lodging is a must in Rising Sun. Enjoy a restful stay at Anderson’s Riviera Inn and the Empire House—both have riverfront views conveniently located in downtown. If camping under the stars is more your style, several sites await your arrival, including Little Farm on the River RV Park, Arnold’s Creek, and Camp Shore Campgrounds in Rising Sun. 

Recommended by Kendal Miller of Rising Sun, Indiana

Franklin, Indiana – POPULATION 25,248

Just south of Indianapolis is the small town of Franklin, Indiana. Full of unique experiences and delicious restaurants making it the perfect small town travel destination that all can enjoy.

House in Franklin, Indiana. As featured in The Best Small Towns and Cities to Visit in the Midwest by The Haute Seeker
The Willard | image by Pam Howard

Do: Check out cult classic and old movies at the Historic Artcraft Theater. The theater was built in 1922 and then renovated in the Art Deco manner in 1948. Have you ever heard of Farm Animal Yoga? It’s similar to goat yoga, but with a variety of animals such as kittens, chickens, goats, and even a pig. Add this specialty yoga class to your itinerary at Tagalong Boutique.

Dine: Indulge in crispy, fresh brick oven pizza or calzones and creative drinks using local spirits at Richard’s Brick Oven Pizza, an establishment with a local following and a specialty homemade alfredo sauce that you must try. Add a glass of wine or a mixed drink like the Hoosier Donkey (Moscow Mule using Indiana vodka). The Willard is another great locally owned restaurant – located right next door to the Artcraft. It’s located in an old home built in 1860, a family of four can easily enjoy dinner with drinks and tip for $70 or less. Finally, you won’t want to leave town without indulging in some ice cream or tasty candy treats at The Hoosier Cupboard.  Stock up on goodies to enjoy on your drive home.

Shop: Shop downtown Franklin and discover antiques, home décor, clothing boutiques, and more. Madison Salvage is a non-profit store containing hundreds of salvaged items – the majority before 1970. With rooms full of treasures such as church pews, old wooden doors, and lighting fixtures, it’s a fascinating place to explore.

Stay: Stay at the newly opened Fairfield Hotel off the I-65 exit.

Recommended by Pam Howard of Our Adventure is Everywhere

Iowa

Pella, Iowa – POPULATION 10,360

Many small towns have their cultural charms, but not quite as charming as that of Pella, Iowa. Located in the heart of Iowa, you’ll find the deeply Dutch town of Pella—a community of over ten thousand that welcomes visitors with their tulips, Dutch Letters, and Vermeer Windmill.

Pealla Lighthouse in Pellla, Iowa. As featured in The Best Small Towns and Cities to Visit in the Midwest by The Haute Seeker
Pella Light House | Image by Katy Flint

Do: Touring the Pella Historical Society Museums and Vermeer Windmill is a great way to get a feel for just how proud this community is to have Dutch roots!  Catch a “show” from their Klokkenspel as a great way to take a pause from walking! 

Dine: In their historic downtown, you’ll find lots of locally owned shops that offer everything from home decor to clothing, baked goods, a Dutch deli, and more. Grabbing a pizza or the gyro platter at George’s Pizza & Steakhouse is a must. If you want to experience traditional Dutch food, head to Dutch Fix for Poffertjes, frites, or olibollen.

Shop: Before leaving town, make sure to visit Jaarsma Bakery for a couple of Dutch letters and stop at VanVeen Chocolates for some of the very best homemade chocolates you’ll ever have! If you can, plan a visit during Tulip Time (traditionally the second weekend in May) as it is unparalleled to any other Dutch festival around.  

Stay: When visiting, a stay at the Royal Amsterdam along Molengracht Plaza is a must.  This boutique hotel has been recently renovated and gives easy access to the downtown area of this cool city. 

Recommended by Katy Flint of Flint & Co.

Decorah, Iowa – POPULATION 10,360

Part of the Driftless region (southeast Minnesota, southwest Wisconsin, northwest Illinois, and northeast Iowa), Decorah, Iowa is a stunning small town surrounded by picturesque countryside. If you need to unplug and unwind—do it in Decorah.

Luna Valley Farms Cherry Pie Pizza | Image by Anita McVey

Do: Fly fishing guides in this area provide an outstanding resource for beginners and experienced anglers alike. Scenic parks, trails, and rivers call visitors to hike, bike, and kayak. Adults and children alike will always remember a visit to the unique outdoor classrooms of the Fish Hatchery and Seed Savers Exchange. 

Dine: Whether you are looking for a hearty breakfast, a casual lunch, or an upscale dinner, this town has a strong focus on fresh, local food sourcing. Create your own “Foodventure” and explore the surprisingly diverse menus of the area. Dine in the historic Hotel Winneshiek, enjoy wood-fired pizza at Luna Valley Farm, sample award-winning beers from Toppling Goliath, or pack a picnic and spend more time in the beauty of Decorah, Iowa.

Shop: Stroll the downtown area of Decorah and discover the historical architecture of the buildings. Shop the many small business boutiques, get a spa treatment, or visit one of the museums celebrating the history of this area.

Stay: A wide variety of affordable lodging options are available in this area. Whether you are looking for a glamping experience (Luna Valley Farm), a family stay (Dry Run Cabin), or a downtown suite (Decorah House), Decorah will provide abundant hospitality.

Recommended by Anita McVey of Picnic Life Foodie

Kansas

St. Francis, Kanas – POPULATION 1,294

If the words “Kansas” and “canyons” don’t seem to fit together, you need to visit St. Francis, Kansas. This small town is home to the Arikaree Breaks. At the Breaks, you’ll be surrounded by deep gashes in the earth, wide vistas of gorgeous skies, and the West’s signature sagebrush and yucca plants. If you are looking for a small town that embraces nature— visit St. Francis, Kansas.

Canyons in St. Francis, Kansas. As featured in The Best Small Towns and Cities to Visit in the Midwest by The Haute Seeker
Arikaree Breaks | Image Roxie Yonkey

Do: Visit the Cheyenne County Museum and learn about famous residents. Or the St. Francis Motorcycle Museum. The museum houses more than 130 motorcycles. Thirty of them were made before 1929. If you are looking some outdoor fun, take a half-day road trip to the Arikaree Breaks

Dine: Stop at Fresh Seven Coffee and try house-roasted gourmet coffee from around the world, plus gourmet food. Enjoy pool and burgers at Diamond R Bar & Grill. 

Shop: Find every gift for any imaginable occasion at Donna’s Gift Palace.

Stay: Stay at Spencer House Bed and Breakfast. If possible, reserve the Boudoir suite and enjoy the stargazing balcony.

Recommended by Roxie Yonkey of Roxie on the Road

Lindsborg, Kansas – POPULATION 3,288

Lindsborg, Kansas, aptly deserves its nickname, ‘Little Sweden USA.’ This warm and welcoming small town is immensely proud of its cultural heritage—displayed through festivals, art, and history.

Group gathered for an outdoor festival in Lindsborg, Kansas. As featured in The Best Small Towns and Cities to Visit in the Midwest by The Haute Seeker
Image | Visit Lindsborg, Kansas

Do: History buffs appreciate the Old Mill Museum – a miniature historical village – and a hilltop monument built in honor of Francisco Vazquez Coronado’s local explorations. It’s a great place for stunning countryside views, too. There’s no better time to visit Lindsborg than when the town is celebrating, whether you appreciate vintage autos (Smoky Valley Classic Car Show); or evenings beneath the stars (Broadway RFD Outdoor Theatre). Attend the lively Lindsborg Street Dance, held each summer, a two-day Swedish-themed fall festival (Svensk Hyllingsfest), and annual festivities scheduled that fill the calendar from early November to year’s end.

Dine: Enjoy appetizers and lingonberry margaritas at the Swedish Crown Restaurant. Eat where former Soviet leader Mikhail Gorbachev dined by visiting the legendary Ől Stuga restaurant.

Shop: Brightly painted, life-sized Dala horses stand near numerous downtown businesses such as Hemslöjd Swedish Gifts and Swedish-themed toys in a nearby store. You’ll find museums, galleries, and shops, packed with local art from many decades, including gorgeous nature images by National Geographic photographer, Jim Richardson at his Small World Gallery

Stay: While visiting Lindsborg, stay the night at the Seasons of the Fox. A terrific bed and breakfast.

Recommended by Lisa Waterman Gray of Packed…A Travel Blog

Abilene, Kansas – POPULATION 6,300

Abilene is a small town full of history and fun. This quaint city features award-winning restaurants, magnificent mansions, and so much more.

Historic Seelye home in Abilene, Kansas. As featured in The Best Small Towns and Cities to Visit in the Midwest by The Haute Seeker
Seelye Mansion | Image by Visit Abllene, Kansas

Do: Visit the Presidential Library, Museum, and childhood home of the 34th President Dwight. D. “Ike” Eisenhower. Check out the historic Seelye Mansion, named one of the ‘8 Wonders of Kansas – Architecture’. Hop aboard the Abilene & Smoky Valley Railroad, a 100-year-old steam engine, a train that takes riders on a 10½ mile round trip through the Smoky Hill River Valley to the neighboring community of Enterprise, KS. In Enterprise, the train stops for passengers to see the Hoffman Grist Mill, with a rebuilt working waterwheel that mills flour.

Dine: While in Abilene, grab a bite to eat The Brookville Hotel, a James Beard Foundation Award-Winning hotel and restaurant famous for their fried chicken. Or you can dine the President at Mr. K’s Farmhouse, one of Dwight D. Eisenhower’s favorite farmhouse-style restaurant, well-known for its pies. If you are looking for something more modern, checkout Ortus Café – Abilene’s newest restaurant features a variety of sweet and savory crepes.

Shop: Explore shops at the Abilene Downtown Antique Mall and boutiques such as C’est La Vie.

Stay: The Holiday Inn Express or Engle House Bed & Breakfast.

Recommended by Julie Roller Weeks

MICHIGAN

Charlevoix, Michigan – POPULATION 2,499

Charlevoix, Wisconsin is a small town destination that offers world-class events, fantastic food, fun activities for the whole family, and boasts one of the top main streets in the country. Charlevoix is a fun family destination, no matter what time of year you visit.

Light house on the end of a pier in Charlevoix, Michigan. As featured in The Best Small Towns and Cities to Visit in the Midwest by The Haute Seeker
Charlevoix, Michigan | Image by Melody Pittman

Do: Sailing and boating are accessible on any of the four bodies of water in this town. Choose from Lake Michigan, or the Pine, Charlevoix, or Round Rivers. The coolest thing to see and do in Charlevoix (pronounced char-la-voy) is to tour the Mushroom Houses. Designed by eccentric Earl Young, there are 26 remaining gnome-like houses in the area. The dwellings have curved eaves, exquisite stonemasonry, and look like they have melting roofs. You can do a self-guided tour of the mushroom houses, or take a one-hour tour available through Elements Gallery.

Dine: The Cantina is excellent for sipping perfectly-salted margaritas and eating chips, salsa, and tacos. Or, venture around town to The landing, where fish & chips and shrimp are the most popular items on the menu.

Shop: Charlevoix’s downtown is chock full of high-end specialty shops. I loved Elements Gallery (glassware, collectibles, local artwork), Cherry Republic (a collection of anything and everything cherry—Michigan is the Cherry Capital of the World!), and Color Wear (ladies fashions and accessories). Be sure to pick up the most delicious taffy at Taffy Barrel, a retro-looking candy shop, or enjoy fine chocolates from Kilwin’s Charlevoix. Another sure to please hotspot is Round Lake Bookstore. 

Stay: You may want to stay overnight in nearby Petoskey at The Terrace Inn, a 100-year-old haunted inn. 

Recommended by Melody Pittman of Wherever I May Roam

Minnesota

Northfield, Minnesota – POPULATION 20,634

Northfield, Minnesota, is a fascinating town of about 20,000 on the Cannon River, about 40 minutes south of Minneapolis. It’s a fantastic Midwestern destination all its own. With a motto like “Cows, colleges, and contentment,” you know you’re in for a treat when you visit Northfield.

License plates in Northfield, Minnesota. As featured in The Best Small Towns and Cities to Visit in the Midwest by The Haute Seeker
Makeshift Accessories | Images by Kristie Probst

Do: It’s got two well-respected private colleges, Carleton and St. Olaf, and the college town vibe to go with them. And it’s got a tremendous annual celebration commemorating when the townspeople banded together back in the 1800s to chase Jesse James and his brother out of town while stopping his gang from robbing the First National Bank. How many cities can boast all of that? If you love the great outdoors, Nerstrand-Big Woods State Park, about 20 minutes outside Northfield, is a lovely place for a stroll. Make sure to check out Hidden Falls!

Dine: Froggy Bottoms, not because it’s the best cuisine in town, but because it has a menu to appease the food tastes of even the pickiest eaters. Froggy Bottoms is a charming basement pub with a lovely patio overlooking the Cannon River. After lunch, treat yourself to cookie dough and a cupcake at Cake Walk. Yum! 

Shop: The well-preserved historic downtown is filled with fun, quirky shops, and a ton of history. Check out shops like Makeshift Accessories, an eclectic store featuring up-cycled accessories made from everything from coins to brass cash registers to silver services and Minnesota license plates.

Stay: You will always feel at home at the Archer House. This downtown Northfield hotel is a lovely, historic place to stay in this small town.

Recommended by Kristie Probst of World is Wide

Ohio

Bowling Green, Ohio – POPULATION 31.578

Bowling Green(BG) is a funky little college town in Northwest Ohio. BG is full of personality, places to go, and plenty of opportunities for all.

Image | Visit Bowling Green

Do:  Visit nationally award-winning places like Grounds for Thought, a coffee shop known for its delicious blends and rotating art gallery, or the Wood County Museum. This former county poor farm currently houses exhibits devoted to local history. Bowling Green is also home to national events like the National Tractor Pulling Championships and Black Swamp Arts Festival. Visit the first Wind Farm in Ohio or explore the trails and get some fresh air, BG is green for miles!

Dine: Want something a little more low key in this cool city? Search for Bowling Green Beer Works, BG’s hidden nano-brewery that offers great beer and art to those that love a good treasure hunt.

Shop: Spend your day shopping at retail shops that bring visitors back again and again. Discover new music and classic favorites at Finders Records, one of Ohio’s oldest independent record stores. Relive your childhood by purchasing a retro video game from Rock Em Sock Em Retro.

Stay: Bowling Green’s many hotels offer clean, affordable lodging for you or groups of up to 93 guests. BG’s Best Western Hotel won the 2019 M.K. Guertin Award. This award recognizes the best performance across areas such as quality assurance, customer service, guest satisfaction and commitment to the Best Western brand.

Recommended by Carmen Camo of Visit Bowling Green

Athens, Ohio – POPULATION 24,688

In southeastern Ohio, you’ll find the picturesque college town of Athens, Ohio, a small town full of activities, charm, and Ohio University pride.

Downtown Athens, Ohio | Image William Flood

Do: The list of area activities is impressive. If you are a sports fan, be sure to take in a Bobcat football game. Arts lovers can enjoy a movie at the Athena Cinema, which has continuously shown film since 1915.  Road trippers can hit the nearly 1,000 miles that comprise Ohio’s “Windy 9” or drive along the local stretch of America’s Loneliest Road, U.S. 50.  At day’s end, snag a room at the Ohio University Inn & Conference Center, just a short walk from campus.

Dine: When hunger calls, consider Bagel Street Cafe, a campus institution, or Casa Nueva, known for sustainable Mexican-inspired cuisine. Uptown is also home to four coffee shops, including Donkey Coffee, where you can enjoy Bohemian digs filled with OU students. For craft spirits aficionados, Athens boasts 11 wineries, breweries, and distilleries

Shop: Athens’ walkable Uptown, anchored by Court Street, is filled with authentic dining and shopping options. Start by hunting down some campus swag at College Bookstore.

Stay: Snag a room at the Ohio University Inn & Conference Center, just a short walk from campus. Another great lodging option is Burr Oak Lodge, overlooking 660-acre Burr Lake, inside picturesque Burr Oak State Park, part of the Great Ohio Lodges system, and just under 20 miles from town.

Recommended by William Flood of William Flood.com

Yellow Springs, Ohio – POPULATION 3,702

Like many small towns with a rich history, the well-known ‘hipster’ city of Yellow Springs is infamous for its art, activism, and natural resources. This small town has grown in popularity because of it’s most well-known comedic resident, Dave Chappelle. It continues to draw in visitors and locals with it’s eccentric—yet Midwestern charm.

Stained glass windows at Yellow Spring, Ohio | Image by Taylor Justin

Do: Take a walk through one of the many scenic nature preserves and parks in Yellow Springs. Stretching across 100 acres, John Bryant State Park, Clifton Gorge State Nature Preserve, and Glen Helen Nature Preserve, respectively, offers a wide range of outdoor activities. If you are interested in learning more about the history of this small town, take a Blacks in Yellow Springs Tour, led by local youths from the area.

Dine: Emporium Wines and Underdog Cafe and Ye Old Trail Tavern are where the locals go for coffee, conversation, classic eats. Emporium Wines and Underdog Cafe is part coffee shop part liquor store, while Ye Old Trail Tavern has been serving up craft brews German-themed ho’s d’ oeuvres, salads, sandwiches, and pizza since 1827. For dessert, be sure to grab homemade ice cream straight from Young Jersey’s Dairy farm. While you are there grab some ice cream or cheese to go from their store,

Shop: Downtown Yellow Springs offers an eclectic array of shops and galleries. Scavenger your way through colorful buildings and discover everything from vintage records and handmade stain glass windows to imported goods and on-trend tees form shops like Heaven on Earth Emporium, Wildflower, and Tibet Bazaar.

Stay: Enjoy an intimate stay at the historic Mills Park Hotel, a modern yet luxurious hotel in downtown Yellow Springs. The hotel located near plenty of dining and shopping options, including Ellie’s, a lobby-level restaurant & bakery that offers both indoor and porch seating.

Recommended by Taylor Justin of The Haute Seeker

Wisconsin

Hayward, Wisconsin – POPULATION 2,301

Hayward, Wisconsin, is a small town destination that offers world-class events, fantastic food, fun activities for the whole family, and boasts one of the top main streets in the country. If you are looking for small towns with family-friendly activities, look no further than Hayward for your next family trip.

Image | That Was A First

Do: Your family can spend the day wandering among the animals at Wilderness Walk, or enjoy a live show at Scheel’s Lumberjack Village.  You can visit the Freshwater Fishing Hall of Fame, and don’t miss taking a family photo inside the mouth of the four-story-high musky. Depending on when you visit, you may witness the American Birkebeiner cross country ski race, the Chequamegon Fat Tire Festival, or the Lumberjack World Championships.

Dine: Everyone will find a new favorite ice cream flavor at West’s Dairy, but first, eat the thin crust pizza at Coop’s or at one of the many Friday night fish fry’s’ in the area. 

Shop: Before you leave town, stock up on the penny candy, fudge and taffy at Tremblay’s on Main Street, or grab a loaf of fresh bread from the Hayward Bakery.

Stay: Flat Creek Lodge. It’s on the edge of town and just a short walk to the Freshwater Fishing Hall of Fame. There is also a full-service restaurant attached that serves a delicious meal.

Recommended by Vicki Chido of That was a First


Why You Should Visit These Small Towns and Cool Cities

I have found that my most cool and memorable experiences have taken place outside of the “popular” vacation destinations or spots throughout my travels. These experiences usually include off-road diners—hidden gems and historical landmarks often discovered in small towns across the nation.

As you plan your next vacation, consider opting out of the big city and make your way to the surrounding small towns for cool attractions and recommendations from locals that love their cities.

Comment below with a small town that you can’t wait to visit!


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22 Comments

  1. Charlene Rhinehart

    Thanks for sharing! I love to travel but usually don’t travel much in the midwest even though I live in the big, vibrant city of Chicago, IL. I’m not too familiar with Casey, IL so thanks for sharing more about small towns in the midwest.

    1. Taylor Justin

      I live in Chicago as well and was so happy to create this list of places that was nearby. Maybe I will see you on the road to one of these fantastic destinations!

    1. Taylor Justin

      Totally understandable. I encourage you to visit a town that you can stop by for just a few hours. I am sure that community would appreciate any and all love that it receives.

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