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.
The exact dates of events may vary from year to year. Call the Chamber of Commerce at (574) 825-4300 to speak with one of our helpful information specialists.
Year Around Historic Middlebury Self-Guided Walking Tour
Guides are available at the Middlebury Chamber & Visitors Center, 118 S. Main Street.
Faces of Middlebury, May – September
Grab your cameras and the map to locate each “face of Middlebury” and insert your face for the perfect picture. Maps are available at local businesses and organizations.
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 essenhaus.com.
Farmer’s Market @ The Mill
It is open every Saturday morning from May through September 21. It is outdoors at The Mill, former Wanberg Popcorn Plant, 402 E. Warren Street. The market is open from 9 to 1, rain or shine. Vendors sell their produce, baked goods, florals, soaps, and more! Call (574) 538-0116.
Middlebury Literary Carousel, May 5
9 am – 4 pm sessions & activities followed by Dinner and a Book. Session content includes authors & presenters for children, teens & adults as well as activities for all ages. Activities and sessions will be held at the library, museum, Krider Garden, Memorial Park & East Park with Dinner and a Book taking place at Greencroft Middlebury’s Community Senior Center. All sessions/activities are free of charge with the exception of Dinner and a Book which will have a nominal fee/reservation.
Middlebury Annual Garage Sale Days, May 16-17
This annual epic town-wide garage sale occurs May 16-17, 9 – 5. The Community Garage Sale map and guide are coming soon. Happy hunting! Want to be involved? To be placed on the town-wide garage sale map, we must receive your completed registration form (PO Box 423 or 118 S. Main Street) and the $15 payment by May 2, 2025, to be placed on the physical map and online. Questions? Contact 574-825-4300.
Memorial Day Dusk-to-Dawn Vigil & Parade (est. 2004)
Beginning at dusk on Sunday until dawn on 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 graves of each veteran. The traditional observance begins at 10 am. on Monday when the Post Honor Guard leads the parade up Main Street to Memorial Park. Visit marklwiltpost210.com.
June
Flashback Friday Movies in the Park, June 18, July 20, August 15, 2025
Family-friendly movies on the 3rd Friday of June, July & August at 8:00 pm at Riverbend Park, 511 E Warren St.
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 pumpkinvine.org.
The Middlebury Summer Festival (est. 1968)
Held annually in June downtown June 27-28, 2025). The festival features locally grown produce, food vendors from local restaurants, churches, food truck vendors, live music, artisans, crafts, a cornhole tournament, a basketball tournament, a tractor pull, and children’s activities. The Summer Festival Parade is one of the state’s largest and longest-running parades.
July
August
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 middleburyin.com.
September
Middlebury Fall Festival
Held annually in September( September 5-6, 2025). The festival features locally grown produce, food vendors from local restaurants, churches, and food truck vendors, live music, crafts, mums, produce, and pumpkins. Stay until dusk to watch one of the most extensive fireworks displays in Michiana, located at the Essenhaus Campus.
October
Middlebury Pumpkin Race, October 12
Grab your crew of family, friends & neighbors, purchase a race kit, design your pumpkin and have some serious fun! Pit Row opens at 1:00 pm for those wanting assistance with drilling holes/assembling axles; the race begins at 2:00. 400 block of West Warren St. Free registration.
Halloween Parade at the Memorial Park
Enjoy family-friendly fun at the annual costume parade hosted by our local firefighters. Visit middleburyin.com.
November
Middlebury Hometown Holidays
An annual tradition is 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, or contact Varns & Hoover Hardware..
December
Christmas Tree Lighting, December 4, 6:00 pm
Join the Community at Memorial Park and experience the sights, tastes, and sounds of Christmas: Cocoa, Cookies, Christmas Carols, and a craft.
Christmas at The Mill, December 14th
It’s Christmas at The Mill. Come out and celebrate the holiday season with the whole family at this festive event with SO many special things happening, including Mr. and Mrs. Claus!
A Very Merry Happy Hour, at The Mill, December 19th
Join The Mill for the merriest happy hour of the season in downtown Middlebury, where they will host a pop-up happy hour event from 5 to 7 p.m.! Mocktails + AMAZING deals as you finish crossing off the rest of the names on your list!!
West on Warren – Gallery + Grill, 200 W Warren St.
Tues- Sat: 11 am – 2 pm and 4pm – 9 pm; Sun: 10 am – 2 pm – local art on display and fine dining.
Wedgewood Brewing Company, 129 Orpha Drive Suite D.
Friendly Atmosphere, Dine-in Menu, featuring Craft Beer and Rock’ N Roll. Open 11 am – 9 pm Wednesday & Thursday, 11 am – 10 pm Friday’s, 12 pm – 10 pm Saturday’s, and 12 pm – 8 pm on Sunday’s. Check out their new Event Center Wedgewood Live! Party Venue located at 131 Orpha Drive
OTHER
Middlebury Parks Activities in 2016. Park Events 2018
Middlebury Breakfast Optimist Trivia Night
March 9 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, the 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.
Trivia Sponsor-Table Registration-2018-KAM
Trivia Raffle Donation-2018-KAM
Trivia Night Poster-2018-KAM
Trivia Raffle Donation-2018-KAM
Trivia Night Poster-2018-KAM