Festivals & Events

Middlebury offers fun, enjoyment, and relaxation for people of all ages and interests year-round. If you are looking for a destination to experience and enjoy the community spirit of a small town, try attending one of our festivals or events.

May
Middlebury Community Garage Sales. Essenhaus Classic Car Cruise-In happens each Thursday night, May thru September! Enjoy the family-friendly activities that include live entertainment, door prize giveaways and shopping & dining discounts.

June
The annual Pumpkinvine Bike Ride passes through Middlebury on the third Saturday of June. The Pumpkinvine Nature Trail is the backbone of the Trails of Middlebury and is considered of the top rails-to-trails in the State of Indiana.

The Middlebury Summer Festival is held annually on the last weekend in June in the downtown parks. The Summer Festival Parade is one of the State’s largest festival parades. The Race is back! Come and enjoy all the fun, games and food!!

August

The Middlebury Chamber Golf Classic is held annually on the second Friday of August. The Park Department has an annual Riverfest held at Riverbend Park. Riverfest includes a fish shocking
demonstration, various informational booths, and kayaking on the Little Elkhart River.

September
The Middlebury Fall Festival is held annually on the second weekend in September. The Fall Festival features locally grown produce, food vendors from local restaurants and churches, crafts, movie, fireworks, Jeep Show, Cornhole Tournament, and much more.

November
Middlebury Hometown Holidays is an annual tradition held the Friday before Thanksgiving each year in Middlebury when people gather downtown for shopping, eating, music, and socializing. Visit the Hometown Holidays/Middlebury Then and Now Facebook page for detailed information. Small Business Saturday is an annual event held on the Saturday after Thanksgiving each year.