Guided Walking Tours by Middlebury Then and Now

Gangsters, Saloons & Buggies on Roofs

Historic Middlebury is full of surprises.  John Dillinger was the most famous criminal in the U.S. in the 1930's 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, event at Walmart...but on a roof?  Hear these inside stories, secrets and more from a local with this tour of downtown.

Meet at Middlebury Community Library, 101 E. Winslow

Trip Tip:  Spend some extra time in downtown Middlebury exploring the unique shops and restaurants.

Tour Information

Tours will be available at designated times during the Summer Festival and Fall Festival

Other times and group rates are available by advance request

Thanks to our generous sponsor, 1st Source Bank, the tours during the festivals will be free of charge.

Giant Toadstools and the World's Fair

Take a guided tour through living history!  The Krider family of Middlebury once captured the imagination of the  world.  This tour of the park that bears their name opens a window to the family's nursery at the height of its creative powers.  The natural beauty will take your breath away.  You may even spot a giant toadstool.  This tour is great for kids so grab the family and the camera; there are plenty of opportunities for fun selfies.

Meet at the Middlebury Community Historical Museum, 301 W Bristol Ave

Trip Tip:  Take some time to explore the Middlebury Community Historical Museum to learn more about Middlebury's historic past.

Questions?  Send us an email at or call 574.825.5601

Helpful Hints:

Please wear comfortable shoes and dress appropriately for the weather.  Tours continue during rain or shine.