I do not know if I would call it a "festival" but these locations all have pumpkins and apple picking and cider and cider donuts each fall. I know that Brooksby has animals and hay rides too. Smolak also does hayrides.
Russel Orchards, Ipswich
Smolak Farms, North Andover
If you are into Halloween fun, the October Halloween Festival in Salem (easy 30 min drive from Gloucester) is full of arts and crafts, street entertainment, local attractions such as Old Burying Ground Cemetery and Witches Memorial, House of Seven Gables, and many visitors dressed in costume which lend to the festive nature, as well as the maritime attraction of a coastal seaport, removed from the hustle and bustle of the festival. Mostly all attractions are within walking distance to each other. Downside is the parking ramp fee which provides all day central parking, is $20, but relieves one from the annoying task of feeding meters and moving cars on the crowded streets. There is certainly enough to see and do to provide a leisurely day's entertainment.
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