Hank's Pumpkintown

Sure, the name may be misleading, but this Water Mill institution is a fantastic choice for apple picking if you’re Out East. At Hank’s Pumpkintown, $30 gets you a one-peck bag (a peck, by the way, works out to approximately 10 pounds) of apples like Jonagolds, Cortlands, or Cameos. And yes, it’s also worth visiting closer to pumpkin season, when 30 acres of attractions will delight the inner-child in anyone (but be warned that it is incredibly popular, so plan ahead). Activities include narrated hayrides, gem mining, a 7-acre corn maze, and classic fall snacks like Apple Cider Doughnuts and Hand-Dipped Caramel Apples. And, of course, don’t forget to grab a fresh-baked pie from their market on your way out.
By public transport: 2 hours and 35 minutes. From Penn Station, take LIRR to Jamaica Station, then transfer to the Montauk Branch. Exit at Southampton and take a taxi two miles to Pumpkintown.
By car: 2 hours and 20 minutes