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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! We invite you to revel in the final golden days of summer along gaslit streets lined with hundreds of craft vendors, strolling entertainers and the mouth-watering aromas of delectable festival treats!