Historical walking tours offered in Middlebury

Historic walking tours offered in Middlebury

A pair of one-hour guided walking tours began on May 31 in Middlebury, offering residents and visitors alike the opportunity to glimpse back a little way into the town’s history.

Gangsters, Saloons and Buggies on Roofs

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 on the roof? Hear these inside stories, secrets and more from a local with this tour of downtown.

Meet at the Middlebury Public Library on Winslow Street.

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 into 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 or camera phone. There’s plenty of opportunities for fun selfies.

Meet at the Middlebury Community Historical Museum.


Walking Tours Information

Tours began Wednesday, May 31, and will continue through September 28.

Wednesdays at 10 a.m. – Gangsters, Saloons & Buggies on Roofs.

Thursdays at 10 a.m. – Giant Toadstools and the World’s Fair.

Other times available by advance request.

Cost of the tour is $5 per person and is non-refundable. Tips welcome.


Helpful Hints

These are walking tours. Please wear comfortable shoes.

You might want to bring a bottle of water

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.


Go to htadventures.com/walkingtours for details and reservations.