Gangsters, Saloons & Buggies on Roofs - Downtown Middlebury Walking Tour 

Historic Middlebury is full of surprises. John Dillinger was the most famous criminal in the U.S. in the 1930s and it is rumored he passed through Middlebury and even spent the night in a boarding house.

In Amish Country, it’s not unusual to see buggies everywhere; on the roads, at banks and grocery stores, even at Walmart, but up on a roof?! Hear these inside stories and secrets and more from a local with this tour of downtown.

Buy Tickets 

*To secure your spot in the tour, we recommend buying your tickets 24hrs BEFORE the tour starts.* 
*Last-minute registrations/ticket purchases at the tour meeting time are also welcome.*

Tour starts at the Middlebury Public Library at 10am. Meet out front, by "Elkabet" the elk. We recommend reserving your tour time and date by registering online or by stopping in the Middlebury Chamber of Commerce Visitors Center, 201 South Main Street, Middlebury, IN.

• This is a walking tour. Please wear comfortable shoes.
• Tours go rain or shine. If it is calling for rain, you might want to bring an umbrella or wear rain gear
• Please arrive 15 minutes prior to your tour’s starting time.

Additional tour dates available by request.
Is your group over 15 people? Contact us to learn more about large group rates.