Community Events

Middlebury is home to a wide variety of festivals and special events held throughout the year. Below you’ll find a brief selection of annual events, organized by month, you can expect to happen each year in Middlebury, Ind.

Exact dates of events may vary from year to year, so be sure to check the website listed or call the Chamber of Commerce at (574) 825-4300 to speak with one of our helpful information specialists.


Essenhaus Classic Car Cruise-In

Every Thursday night, May through September. Enjoy the family-friendly activities that include live entertainment, door prize giveaways and shopping and dining discounts. Visit

Farmer’s Market @ Sycamore Bend

Open Saturdays 8 a.m. to 1 p.m. mid-May through mid-September. Located outdoors at the former Wanberg Popcorn Plant, 402 E. Warren Street. Call (574) 538-9543.

Memorial Day Dusk-to-Dawn Vigil & Parade (est. 2004)

Beginning at dusk on Sunday until dawn Memorial Day the members of American Legion Post 210 post an Honor Guard at the entrance of Grace Lawn Cemetery, and the Boy Scouts place battery-powered lights on the grave of each veteran. The traditional observance begins at 10 a.m. on Monday when the Post Honor Guard leads the parade up Main Street to Memorial Park.Visit


Annual Pumpkinvine Bike Ride (est. 1999)

This popular ride passes through Middlebury on the third Saturday of June. The routes range from 10 to 101 miles and are suitable for bicyclists who want a vigorous workout as well as those who want to bicycle at a leisurely pace on the Pumpkinvine Nature Trail and on county roads. Experience horses and buggies, farm animals in fields, flower gardens, country schools and small towns. Learn more at


Trails of Middlebury Celebration

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


The Middlebury Summer Festival (est. 1968)

Held annually on the second weekend in August in downtown. Live music, festival food, crafters, children’s’ activities. The Summer Festival Parade is one of the state’s largest and longest-running parades. Learn more at

Riverfest in Riverbend Park (est. 2009)

Hosted by the Parks & Recreation Department – includes a fish shocking demonstration, various informational booths and kayaking on the Little Elkhart River. Visit


Middlebury Fall Festival

Held annually on the third weekend in September. The festival features locally grown produce, food vendors from local restaurants and churches, live music, crafts, mums and pumpkins. Stay until dusk to watch one of the biggest fireworks displays in Michiana. Learn more at


Halloween Parade at the Fire Station

Enjoy family-friendly fun at the annual costume parade hosted by our local firefighters. Visit


Middlebury Hometown Holidays

An annual tradition held the Friday before Thanksgiving. Locals gather downtown to shop, eat, socialize and enjoy festive music. Find “Middlebury Hometown Holidays” on Facebook for more details.

Friday Night Tee Time at the Library & Saturday Mini Golf

Annual fundraising event that supports the Middlebury Community Public Library, Trails of Middlebury and the Middlebury Historical Museum. Learn more at

Late Night Entertainment Year Round

Heritage Hall on the Essenhaus Campus, 13489 C.R. 16

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. Visit

41 Degrees North, 104 S. Main Street

A family-friendly establishment on Main Street in downtown featuring local food in a renovated bar with cocktails and regional beer. Open until midnight Fridays and Saturdays. Find “41 Degrees North” on Facebook or call 574-358-0314 for more details.

Rulli’s Bella Luna Sports Bar (21+), 851 US-20

Thursday nights are karaoke night, followed by live music every Friday and Saturday. Sports lovers can find their favorite game on one of ten 60” HD televisions.Open until 11 p.m. Fridays and Saturdays. Visit


Indiana Swimming North Central Divisional Championships
For the first time, the Northridge Area Swim Association has been chosen to host the 2016 Indiana Swimming North Central Divisional Championships at Northridge High School on March 4-6. NASA is looking for businesses to partner with them in hosting 400+ swimmers, along with their families, during this 3-day championship swim meet. Deadline for inclusion is February 20, 2016. Download files HERE: Divisional Cover Letter 2016 and Divisional Sponsor Form.
Middlebury Parks Activities in 2016Park Events 2016
Middlebury Breakfast Optimist Trivia Night
March 18 from 6 to 9 p.m. at Northridge High School.
Put your thinking caps on and come on out for a night of challenging trivia and raffle prizes!
Proceeds benefit Northridge Dollars for Scholars, Boys & Girls Club of Middlebury and several other community youth programs.
Sponsorships, Gift Certificate Donations, & Tickets are all available by calling Kris Mueller @ (574) 536-0774.