18 Ditch Plains Road, Montauk
This is The End -- the tip of the South Fork where you’ll find the best waves for surfing. Whether you’re an expert or a novice, at Ditch Plains (an actual point break) you’ll be a regular Johnny Utah in no time. Rent a board and sign up for a lesson at the Air and Speed Surf Shop, a five-minute drive from the beach. If you’d rather hang fewer than 10, the extra long break of the waves makes body-surfing, boogie boarding, and paddle boarding livelier than in calmer waters. Be warned, though: The waves can get intense -- lifeguards are stationed here for a reason.
Its remote location on the island makes this stretch of beach along the coves perfect for peace, quiet, and maybe a little zen. The three-hour drive here gets you to a main lot that needs a village permit. Instead, take the LIRR from Penn Station to the last stop on the Montauk line, a short cab ride from the beach, or reserve a spot on the Hampton Jitney.
The beach, equipped with showers, is also right by the local Ditch Witch food truck, which has been serving up breakfast burritos, cinnamon buns, and its famous Ditch Witch Cubano to hungry surfers since 1994. When you’re done, take a short ride by car, cab, or bike (you can rent one at the Montauk Bike Shop for $50 a day) to check out the historic Montauk Lighthouse, commissioned by George Washington in 1792. The oldest lighthouse in New York State, it’s kind of a big deal.