UPCOMING EVENTS

• Middlebury Fall Festival (September 11–12, 2026): Held in downtown Middlebury, featuring food vendors, local crafts, produce, kids’ activities, a drive-in movie, Friday night fireworks on the Essenhaus Inn grounds, and a cornhole tournament.
• Pumpkinvine Classic (Saturday, September 12, 2026): A 25th-year annual cycling event starting from Das Dutchman Essenhaus that tours northern Indiana farmland.
• Royal RV Center’s Ultimate Tailgate Party (Saturday, September 12, 2026): A free community event at Royal RV Center with big screens inside luxury RVs, RV tours, tailgate games, and free hot dogs.
• Bonneyville Bird Fest (Saturday, September 12, 2026): A free family-friendly festival at Bonneyville Mill County Park featuring guided bird walks, talks, games, and vendors.
• Feature Grain Day – Khorasan (Saturday, September 19, 2026): An ancient grain grinding and tasting event at Bonneyville Mill with free baked samples and flour bags for purchase.
• Trail Trekkers: Pollinators (Monday, September 21, 2026): A child-focused nature walk and pollinator activity at Corson Riverwoods County Park ($2 per child, registration required by Sept 18). [1]
• Essenhaus Classic Car Cruise-In Finale (Thursday, September 24, 2026): The season finale at the Essenhaus Inn & Conference Center featuring over 1,500 classic and custom vehicles and food trucks.
• Fall Fashion Show (Thursday, September 24, 2026): An outdoor event at Shop Living in Yellow featuring live music, drinks, and clothing deals.
• Market Under the Lights (Saturday, September 26, 2026): An evening market at Joyfully Said with live music, food trucks, and over 40 boutique and vintage vendors ($5 admission).
• LoveWay’s Ride-A-Thon Benefit (Saturday, September 26, 2026): An annual trail ride or hike fundraiser at LoveWay, Inc. supporting equine-assisted services, complete with meals and a silent auction.
• Middlebury Pumpkin Race, October 10, 2026. A Middlebury, IN Then and Now Event -tap the link above for event information.

MIDDLEBURY HOMETOWN HOLIDAYS SMALL BUSINESS CELEBRATION (est. 1993) NOV 20

An annual tradition is held the Friday before Thanksgiving. Locals gather downtown to shop, eat, socialize, and enjoy festive music. The Chamber will give away $2,500 in gift cards, courtesy of Jayco Inc.