I grew up in Salem, and the apple festival the last Saturday in October is an annual staple. The pies are all homemade, but you have to get there early before they sell out. Trigger warning: Politicians are known to be prevalent making their last pitches. ETA that the library has a gigantic book sale the same day down the road at the school gym.

https://www.ctvisit.com/events/salem-apple-festival-0