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.

The Resolution 5k run/1 mile fun walk is each year on January 1. It is designed to encourage people who want to pursue a new healthy lifestyle in 2016 and for seasoned and beginning runners, who are looking for a new winter run. All proceeds benefit the Middlebury Community Food Pantry.

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.

The annual Pumpkinvine Bike Ride passes thruough 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.

Trails of Middlebury Celebration is an annual event that celebrates the Pumpkinvine Nature Trail and the Trails of Middlebury. This event includes trail walks, live entertainment, kids’ activities and a hospitality tent. Funds raised from this event go toward the maintenance and improvement of current and future trails.

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

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. This event is in
August each year.

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

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 Facebook page for detailed information.

The Ice Festival is a great way for families to kick off the holiday season and to enjoy catching up with friends, family and neighbors. The event is on the third Friday in December each year.

Year Round
Essenhaus Heritage Hall offers a variety of special events, activities and performances throughout the year.
It’s an ideal venue for music, concerts, dramas, dinner theatre and is also available for rent.