The AppleUmpkin Festival had its humble beginnings in 1986, the brainchild of one of our most creative residents, Mrs. Willa Bishop. Her objective was to bring the residents of the Town of Middlebury together to celebrate the harvest. Since apple orchards and pumpkin patches abound , Mrs. Bishop came up with the name “AppleUmpkin!”

Early festivals were small and engaging, anticipated and attended by residents of the Town of Middlebury, the Village of Wyoming and the Dale Valley. Houses were decorated in honor of a plentiful harvest, music and dancing filled the otherwise quiet streets, and people of all ages came together for a grand celebration of the harvest!

Schedule of Events

September 27, 2025

Main Street & Village Park

9:00 – 6:00 - Free shuttle service between Village Hall & Handicap Parking at School

10:00 – 5:00 - Arts & Crafts — Show and Sale

Food Court (North End of Park)

Village Hall

9:00 – 5:00 - Antique Show & Sale

9:00 – 5:00 - Natural History Museum Open

Middlebury Historical Academy

10:00 – 5:00 - Open with Exhibits and Special Displays

Wyoming Fire Hall

9:00 – 6:00 - Parking Available

Village Park Gazebo

10:00 – 5:00 - Rest Station