The Midwest is where you can have adventure after adventure in some of the smallest towns in America. Each of these towns offers something special. It’s not uncommon to have a local wave at you as you stop at the lone stop sign in town. Most importantly, kick back and enjoy the atmosphere that each of these small towns has to offer.
Medora, North Dakota
Fewer than 130 people call Medora home. It’s no wonder that many people fall in love with this small charming mountain town on their first visit. The entrance to the South Unit of Theodore Roosevelt National Park is in Medora. An evening at the Steak Fondue and the Medora Musical is one for the memory books. Find your chair in the outdoor amphitheater and enjoy the longest-running outdoor musical in the country. Lace up your hiking boots and hike the world-famous Maah Daah Hey Hiking Trail. If you want a game of golf, Bully Pulpit is one of the top golf courses in the country. It’s not only challenging, but it’s also one of the most beautiful courses you will find in the Midwest. June, July, and August are the prime months to visit, as the attractions are all open.
Planning your trip? Read up on how to spend a perfect day in Medora, North Dakota, or our North Dakota road trip: Fargo to Medora.
Clear Lake, Iowa
Clear Lake is where Buddy Holly played his last concert at the legendary Surf Ballroom. You can hike out to the crash site and relive the music that lives on today. This small town of under 8,000 is also an incredible lake town that offers boating, swimming, and fishing. The 4th of July is the best in the country when it comes to family fun. The parade, lake, picnics, carnival, and fireworks over the lake are incredible. A summer visit must is to enjoy swimming in Clear Lake.
May is a terrific time to hike out to the Buddy Holly Crash Site, as the countryside is beginning to green up. If you do choose to hike out to the crash site, wear proper footwear. The site is approximately a quarter-mile off of a gravel road, and it is often muddy. Be sure to take a selfie with the Buddy Holly glasses that mark the beginning of the trail to hike to the crash site. Book a night’s stay at the award-winning Larch Pine Inn.
If you are an art enthusiast, you probably know about Lucas. If not, you need to know about Lucas! This small town of under 200 people celebrates art in every way, shape, and form. Bowl Plaza is home to some of the most beautiful restrooms (yes, you read that right!) in the world. The Grassroots Art Center is where you can see all types of art. Everything and anything comes to life in this museum. The highlight of my visit to Lucas is always the Garden of Eden.
A gentleman named Samuel Perry Dinsmoor constructed this work of art that many travel for miles to experience. For a small fee, you can take a guided tour of the site. Something unique to this site is that Mr. Dinsmoor is buried in the log cabin mausoleum on-site. There is no photography allowed when viewing his body.
Plan to visit anytime from May through October to enjoy all that Lucas has to offer.
The Volland Store south of Alma, Kansas, is where you can have a night at the museum in rural Kansas. The Loft at the Volland Store overlooks a museum space that rotates out with different traveling displays. I had the opportunity to stay here when a salute to agriculture was on display. Sunrise was gorgeous, as were the deep breaths of fresh air that greeted me as I stepped outdoors. If you enjoy a quiet place without other people around, the Volland Store will interest you.
Have you ever seen a shoe tree? Imagine the smile I had when I saw the shoes on the tree as I drove around the bend on the gravel road that leads to the Kissel Shoe Tree. This is one of the most clever experiences that I have come across in all of my travel. People have been nailing their shoes to this tree since the late 1980s. Many visitors stop to look at this amazing work of art in rural Kansas, and some even nail a shoe to the tree.
This tree is not in Wetmore proper, so you will need to travel to the tree. Travel 1 mile west on K-9 from Wetmore, then 5 miles north on W Road to the old Davis Ranch sign, then turn and go 1 mile west on 90th to V Road. You will not miss the tree, as it is on a corner and it’s on public ground. A hammer and nails are on site, but you do need to bring your own shoe to nail on the tree. I would also suggest bringing a permanent marker to leave a message on your shoe!
If you are a weather enthusiast you most likely know about Codell. Codell was hit by a tornado on May 20th in 1916, 1917, and 1918. Today you can view the 12-foot sculpture that replicates a tornado funnel. Can you imagine what life was like in this town in 1919? The town never recovered from all of the damage that these tornadoes caused, yet the pride in the community lives on today. The Rose Cottage in Stockton offers a cozy night of lodging in Rooks County, and you’ll also find restaurants in town.
Wall, South Dakota
With fewer than 1,000 residents, Wall, South Dakota, home to the iconic Wall Drug Store, swells to accommodate thousands of visitors throughout the year. Wall Drug is one of the most popular stops for millions of people traveling to and through the Black Hills. Travelers have stopped for years for water and coffee. Today you can experience the Old West and enjoy a meal, including pie. Cowboy-themed stores, as well as gift shops, offer something for everyone. There are several choices for lodging in Wall Drug if you need a place to stay for the night. If possible, plan your stop during the middle of the morning or afternoon and eat a late meal here. You can avoid waiting in line for a table or ordering food if you eat at an odd hour.
Washington Island, Wisconsin
To arrive on Washington Island, you will take a ferry ride over from the tip of the Door County Peninsula. Plan to spend a full day exploring this island, which is home to around 700 people year-round. Hike to the top of Mountain Park Lookout Tower for an epic view of the island and its surroundings. I have climbed this tower in spring, summer, and fall.
Fall is incredible with the golden foliage that surrounds the tower. Schoolhouse Beach is one of the most interesting beaches I have ever set foot on. The rocks that make up the beach are stunning and unique. Note that it is against the law to take any of the rocks from the beach home with you.
Kelleys Island, Ohio
One of my favorite things to do on Kelleys Island is to watch the sunset in the evening. During the day, it’s a great time to explore the island by golf cart. Experience the Glacial Grooves and historical sites, and find a place along Lake Erie to kick back and relax. The areas that I have found to sit along the shoreline on Kelleys Island often remind me of a Caribbean beach. If I did not know that I was on a beach in Ohio, I could easily think that I was in the Caribbean.
This tiny island town is one of the best secretive adventures that the Midwest has to offer. I can count on one hand the places where I can hop on a golf cart and explore an island in the heart of America. Hop on the ferry early in the day for a full day of exploring. You can drive your car on the ferry to travel to the island, as well. I have found that a rented golf cart suffices for all travel necessities on the island, though.
Each of these towns has something that you will find unique. The best tip that I can give you is to start a conversation with the local folks. In each of the communities that I have recommended for adventures in the smallest of small towns, you will find local folks who will welcome you. If you need directions on how to get somewhere, roll down your car window and ask. Stop your golf cart along the road and ask. These folks in the Midwest will help you and appreciate that you took the time to visit their communities.
Adventure comes in all sizes, shapes, and forms. I appreciate the fact that many people have taken the time to invest in their towns so that people like you and me will feel welcome when we arrive. Enjoy the home-cooked meals in the diners that you will find along your route. The chances are pretty good that you will be planning a return visit before you leave town.