Montauk: New York
They call it The End. "They" being local reporters writing about Montauk. New Yorkers just know the enduring fishing town as the best surf spot not only on Long Island, but possibly the East Coast. Montauk, the easternmost point in Suffolk County, has always been a getaway from the Hamptons: the place where anyone – a lone fisherman, Robert DeNiro – could escape the east-end glitz.
But the shingled-house village has recently received a vibrant shot in the arm. Montauk is no longer a locals-only marina village with the roughest waves this side of Fire Island. Now you can find stylish boutique hotels and cheffy food in the same zip code as Billy Joel's weathered baymen. That's brilliant, but we prefer to focus on the rustic, windswept qualities of the town, where you can still see sharks hanging on the dock.
The surf spot to hit is Ditch Plains, and we almost feel silly presenting this obvious suggestion since it's so beloved a wave-riding temple. But if you're a Montauk neophyte, pay attention: The choppy waves are often manageable for longboarders, and they break consistently, but you'll be duck-diving over a rocky bottom, and sometimes the currents can get wild. What's more, you'll experience a clogged lineup in summer months, more so now because of articles like this one. But don't be deterred. Just heed the rules that the Surfrider chapter posts: "Courtesy is contagious - Don't be a wavehog"; "Paddle around the lineup; not through it"; and "DON'T DROP IN!!!!" It's pure joy, finding yourself inside a barrel under three hours from Manhattan, but remain mindful that you can easily wipe out on sharp stone. On flat days, the tides are ideal to standup paddle. Or just float around the shallows with sandsharks.
On land, try the daily catch at the Aussie-inspired restaurant Byron at the Surf Lodge, helmed by Chris Rendell. We recommend sleeping there, too, especially if you or a guest find the whitewashed, surf-chic rooms refreshing in a town that's usually awash in shades of gray. Another in-step option, of course, is the relaunched Ruschmeyer's, which has been around for over 60 years, but now offers a glamping wonderland near the town's interior lake. For gear and expertise, hit up Air and Speed Surf Shop. But nothing's stopping you from jumping into the chilled breakers cold. Just carefully study the sets and devotees who made it famous, and save your carving for Rockaway.