Milk Pail Farms

Load up on all the fall favorites at this Hamptons farm, which opened Labor Day weekend for apples and pumpkins. The dwarf apple trees at Milk Pail ensure easy grabbing, while pumpkins ranging from minis to 150-pound behemoths can be plucked straight from the vine. Pricing for a quarter peck bag will cost you $8, and the largest size of a half bushel bag is $50 for varieties like Gala, Honeycrisp, and more. And fun fact: the Halsey family who runs it are, astoundingly, the 12th generation to work the land.
By public transport: 2 hours and 55 minutes. From Penn Station, take LIRR to Jamaica Station, then transfer to the Montauk Branch. Exit at Bridgehampton and take a taxi two miles to the farm.
By car: 2 hours and 20 minutes