"Bostonians can find a Red Apple Farm stand — complete with mini cider doughnuts and lots of fudge — right within city limits, at Boston Public Market. But for pick-your-own apples and more, head out to Phillipston, which includes a farm store and a seasonal “brew barn” full of beer, cider, barbecue, and live music. The pick-your-own schedule for apples runs from late July to late October or early November, but there are other items available, too, including pumpkins, (dig-your-own) potatoes, popping corn, and more throughout October, with the potatoes stretching into November. Find weekly picking condition updates here." - Rachel Leah Blumenthal