The Midwest’s small towns have big stories to tell.
Throughout America’s Heartland, charming small destinations make great stops for group travelers because the communities offer rich cultural heritage, beautifully restored historic architecture, many attractions and amazing dining experiences. Here are six you should consider for your group.
Woodstock, Illinois
Woodstock, Illinois, is the quintessential Hallmark town, with a beautiful historic square and brick-paved streets. The movie “Groundhog Day” was filmed in Woodstock, and groups visiting town can enjoy a walking tour of film locations. Fans of the movie will want to attend Woodstock Groundhog Days, a festival that celebrates the film with walking tours, trivia, movie showings and pub crawls.
The Old McHenry County Courthouse anchors the square, alongside the former Sheriff’s House. The recently renovated buildings, now called Old Courthouse Center, house the Real Woodstock Visitors Center, Woodstock Area Chamber of Commerce & Industry, and Naturally McHenry County and its visitors center, as well as event spaces.
The historic Woodstock Opera House, which is also in the downtown square, offers group tickets to concerts, theater performances, and dance and comedy shows. Orson Welles made his theater debut on the opera house stage as a teenager.
The area is also known for its agritourism opportunities.
Pella, Iowa
Founded in 1847 by immigrants from the Netherlands, Pella, Iowa, has worked hard to promote its Dutch history and culture. It wasn’t until the 1960s — when urban renewal was happening and old buildings were being torn down — that the town’s leaders decide to “Dutchify” them instead. Now, any buildings built or redesigned in Pella must follow guidelines to keep the town looking like a European community.
Groups visitors will feel like they are walking down the streets of Amsterdam as they sample the goods at Dutch bakeries and meat markets. The Vermeer Windmill and Historical Village features the tallest working windmill in the U.S. The re-created 19th-century Dutch village, which was built in 2002, features 18 buildings, including Wyatt Earp’s boyhood home. The Scholte House Museum is the former 22-room home of Pella’s founder, Dominie Henry Scholte, and visitors to Pella will enjoy the hourly chimes of the Klokkenspel, an animated musical clock tower in downtown.
Nearby, groups can enjoy Iowa’s largest lake, Lake Red Rock, for boating, fishing, hiking and biking, or they can climb the 106-foot-tall Cordova Observation Tower in Cordova Park for panoramic views of the Des Moines River Valley. The town is known for two annual events: the Tulip Time Festival in May, which celebrates Pella’s Dutch heritage with parades, costumes and tulip displays, and the Kerstmarkt, Pella’s Dutch Christmas Market, which takes place the first weekend in December.
Frankenmuth, Michigan
Known as Michigan’s “Little Bavaria,” Frankenmuth, Michigan, features a quaint downtown area with charming shops and restaurants. Just 90 miles north of Detroit and 10 minutes off Interstate 75, the town is a popular stop for groups heading from Detroit to Mackinac Island.
Frankenmuth is famous for family-style chicken dinners at both Zehnder’s of Frankenmuth and Bavarian Inn Lodge & Restaurant, and the city is also the home of Bronner’s Christmas Wonderland, the largest Christmas store in the world, which takes up a space larger than a football field.
Group travelers will enjoy cruising on the Bavarian Belle Riverboat or taking a guided tour of the Frankenmuth Historical Museum. The charming town offers several fun group activities, such as pretzel rolling or the Bavarian Blacksmith Experience, which allows groups to take home hand-forged mementos.
The Michigan Heroes Museum highlights military heroes from the state and across the country. The town’s founding church, St. Lorenz Lutheran Church, which was built when the town was founded in 1845, is famous for its stained-glass windows that depict the story of Frankenmuth and its founding. Groups can schedule free tours of the church. Across the street is a replica log cabin that shows how German settlers to the area would have lived when they first arrived.
Arrow Rock, Missouri
The village of Arrow Rock, Missouri, is in the middle of farm fields and boasts a population of 56. It has six museums that are worth a visit, including the Historic Visitors Center, located in Arrow Rock State Historic Site. The state park, which is part of the larger village of Arrow Rock, is one of the first in Missouri and is a popular camping destination with a fishing lake and several walking trails.
The village itself features a boardwalk with several shops and is home to three dining establishments. J. Huston Tavern at Arrow Rock State Historic Site is the largest and can cater lunches for up to 50 on Lyceum Theatre days. The Lyceum Theatre is a regional theater with shows throughout the summer and fall. Its season concludes with a presentation of “A Christmas Carol” in December. There are several festivals throughout the year, including the Arrow Rock Heritage Festival on the second weekend in October. The village is known for being the home of George Caleb Bingham, one of America’s great 19th-century artists. Bingham is famous for his portraits and scenes of river life and politics. His home is a National Historic Landmark and can be visited during a tour.
Friends of Arrow Rock offer a walking tour of the village or tram tours of village attractions, including Bingham’s home and the home and shop of renowned gunsmith John Sites Jr.
Marysville, Kansas
Marysville, Kansas, is known as the “Black Squirrel City” for its small population of these furry creatures. The town pays homage to the squirrels with 51 five-foot-tall black fiberglass squirrel statues that were designed and painted by local and regional artists. Visitors on the hunt for quirky Snapchat and Instagram photos love searching out statues.
The historic downtown is full of restaurants and shops, and the Blue River Rail Trail is a way for visitors to walk and bike between Marysville and Lincoln, Nebraska.
The town was a Pony Express stop in the late 1800s. The Pony Express Barn & Museum is housed in the former stone barn and home station, where Pony Express horses would rest for the night after heading west from St. Joseph. Even though the Pony Express was only in Marysville for 18 months, the mystique of it is a big draw for group visitors from around the world.
The Koester House Museum and Gardens was built in 1876 by one of the town’s founders, Charles Koester. The home boasts original furnishings and 13 beautiful white statues in the gardens. Groups can organize catered lunches or dinners in the gardens, which are in the heart of Marysville’s historic downtown. Marshall County Historic Courthouse Museum, the Historic Union Pacific Depot and the Lee Dam Center for Fine Art all welcome groups.
Winona, Minnesota
Winona, Minnesota, is a historic Mississippi River town with 13 city blocks on the National Register of Historic Places. The town is in the Driftless Area of the Midwest, a region known for its beautiful sweeping bluffs.
At one time, Winona was known as the “Stained Glass Capital of America.” It still has several stained-glass manufacturers where groups can see how stained-glass artwork is created and restored. The Minnesota Marine Art Museum boasts one of the country’s best collections of art inspired by water. It offers docent-led tours, including a garden walk along the Mississippi River.
The Winona County History Center offers museum tours and a step-on guide service, and groups can learn more about the Mississippi River on a Winona Tour Boat cruise.
Winona is home to a food-products manufacturer, Watkins, which has a museum and store where visitors can learn about the company’s 157-year history making award-winning vanilla extracts, sauces and spices. Groups that want a taste of Winona should stop at Bloedow Bakery, which celebrated its 100th anniversary last year.
