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.
Historic Middlebury Guided Walking Tours, May 30-September 27
Gangsters, Saloon & Buggies on Roofs, Wednesdays, 10:00 am and Tuesday evenings, (June 12, July 10, Aug 14, Sept 11), 6:30 pm; meet at the Middlebury Community Public Library, 101 E. Winslow St. Approximately 1 hour. Fee: $5
Giant Toadstools and the World’s Fair, Thursdays, 10:00 am and Tuesday evenings, (June 12, July 10, Aug 14, Sept 11), 6:30 pm; meet at the Middlebury Community Public Library, 101 E. Winslow St. Approximately 1 hour. Fee: $5.
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. Free
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 @ 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.
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 18-19
This annual epic town-wide garage sale takes place May 18-19., 9 am – 4 pm. The Community Garage Sale map and guide are coming soon. Happy hunting! Want to be involved? In order to be placed on the town-wide garage sale map, we must receive your completed registration form and $15 payment postmarked by May 1 or Reister your garage sale online. Questions? Contact email@example.com or phone 574-825-4300.
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 marklwiltpost210.com.
Flashback Friday Movies in the Park, June 15, July 20, August 17
Family-friendly movies on the 3rd Friday of June, July & August at 8:00 pm at Riverbend Park, 511 E Warren St. Free
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.
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 middleburyin.com.
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 middleburyfestivals.com.
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.
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 middleburyfestivals.com.
Middlebury Pumpkin Race, October 13
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; race begins at 2:00. 400 block of West Warren St. Free registration.
Halloween Parade at the Fire Station
Enjoy family-friendly fun at the annual costume parade hosted by our local firefighters. Visit middleburyin.com.
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 www.mdy.lib.in.us.
Christmas Tree Lighting, December 1st, 6:30 pm – Join the Community at Memorial Park and experience the sights, tastes and sounds of Christmas: Cocoa, Cookies, Christmas Carols, and a craft. Free
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 essenhaus.com.
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 rullispizza.com/bella-luna.
West on Warren – Gallery + Grill
Tues- Sat: 11 am – 9 pm; Sun: 10 am – 2 pm – local art on display and fine dining.
200 W Warren St., Middlebury, Indiana
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.