Guided Walking Tours

Tour Information


Gangsters; Saloons & Buggies on Roofs, Wednesdays, 10 a.m. and Tuesday evening June 12,  July 10,
Aug 14, Sept 11 only,  6:30 p.m.   Meet at the Middlebury Community Public Library, 101 E Winslow St.
Approx 1 hour. Fee $5.


Giant Toadstools and the World’s Fair, Thursdays, 10 a.m. and Tuesday evenings June 12, July 10, Aug 14, Sept 11 only, 6:30 p.m.
Meet at the Middlebury Community HIstorical Museum, 301 Bristol Ave.
Approx 1 hour:  Fee $5

  • 2018 Tours will begin Wednesday, May 30 and run through Thursday, September 27.
  • Additional times available by advance request.
  • Tour ticket includes a free gift bag filled with coupons and treats from local businesses.
  • Cost of the tour is $5 per person and is non-refundable. Tips welcome.

Gangsters, Saloons & Buggies on Roofs     WEDNESDAYS, 10 A.M.

Tour of Downtown Middlebury
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 upon a roof?! Hear these inside stories and secrets and more from a local with this tour of downtown.

Meet at the Middlebury Community Public Library, 101 E. Winslow Street, Middlebury, IN 46540

Buy Tickets

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

Giant Toadstools and the World’s Fair           THURSDAYS, 10 A.M.
Tour of Krider World’s Fair Garden
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 or camera phone. There’s plenty of opportunities for fun selfies.

Meet at the Middlebury Community Historical Museum 301 W. Bristol Ave, Middlebury, IN 46540

Buy Tickets

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

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

and don’t miss these!

Quilt Gardens  2018

More than a million vibrant blooms • 19 gigantic gardens and 22 hand-painted super-sized murals • welcoming communities • Viewable FREE May 30 – October 1
Download free 2018 Quilt Gardens Map and 2018 Master Gardener Guidebook


Middlebury Community Historical Museum

Learn more about Middlebury’s remarkable past.

Middlebury Walking Tours provided in part by: