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Festivals Events & Entertainment

peopleMiddlebury's offers fun, enjoyment and relaxation for people of all ages and interests all year long.  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, or visit one of our entertainment venues.  You might find yourself returning year after 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.


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. 
Check it out on You Tube 


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 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.  Come and enjoy all the fun,
games and food!!


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 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 second 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.