Guided Walking Tours
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.
Tours will be available from June thru September
Tuesdays, 4:00 pm - Gangsters, Saloons & Buggies on Roofs
Tuesdays, 10:00 am - Giant Toadstools and the World's Fair
Other times and group rates are available by advance request
Cost of the tour is $5 per person and is non-refundable; tips are welcome
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
Please wear comfortable shoes and dress appropriately for the weather. Tours continue during rain or shine.