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New York City Road Trip to Montauk

New York City Road Trip to Montauk

​It’s a fantasy to drive to the end of the world. But that’s precisely what it’s like to road trip to the easternmost tip of Long Island to the coastal town of Montauk. Montauk is a worthy road trip for a day or more, a mix of family tradition, influencer style and beautiful scenery. Plan on anywhere from three to five hours to reach your destination.

Fuel Up

The Long Island Expressway can be a backlog of traffic any time of the day. You might want to consider two refueling stops for both your car and your stomach. In Islip, the Oconee Diner is as quirky as they come. There’s a typical menu that reads like a small tome, but there’s much more. The host, Guy, greets you like family, even if it’s your first visit. The chef creates not only in the kitchen; he also decorates the diner for the holidays. Around the Fourth of July, you can expect red, white and blue everything. Halloween is a proverbial hoot, and Christmas is a masterpiece of merriment. Kitchen Kabaret in Roslyn Heights is a favorite gas and food stop. There’s a deli, sushi, sandwiches to order, pre-made salads, pizza and more with outdoor seating. Either of these stops will help break up what could be a very long, trafficky drive.

Kitchen Kabaret is the perfect gas and food pitshop en route to Montauk
Kitchen Kabaret (©Meryl Pearlstein)


Montauk has a variety of seafood restaurants mixed up with traditional and high-end favorites. If you arrive in time for breakfast, stop at John’s Pancake House, a New England-y throwback to car trips of the 50s and featured in Jerry Seinfeld’s “Comedians in Cars Getting Coffee” show with Jimmy Fallon. Duryea’s sits on the marina, and you can tie up your boat there should you decide to hit the water as part of your trip. Be sure to order their mammoth, shareable lobster cobb salad. The Inlet Seafood Restaurant is another seafood fave, also with fabulous views of the water. Montauk oysters (pearls) on the half, lobster rolls and an extensive sushi bar are features. On the beach itself, Navy Beach is a nautical oasis indoors with picnic table seating outdoors and a tempting menu of small plates, seafood and creative cocktails. At Gurney’s Resort, upscale Scarpetta Beach offers relaxed outdoor and indoor dining with an Italian flair.

Picnic tables at Navy Beach in Montauk
Navy Beach outdoor dining (©Meryl Pearlstein)


Bring your hiking boots because you’ll want to check out Montauk’s excellent trails. Walking Dunes is so-named because the dunes themselves shift over time. You can climb the dunes, veering off a path that circles the park and ends up on a beach where you can cool your feet in the ocean. Also interesting, there are cranberry bogs in the center of the park. Across the road further East, Hither Hills State Park has trails with ocean views towards Ditch Plains Beach, the favored beach by surfers. Gurney’s Resort also has beach access for beachcombing or lying out. If you simply want a view of the end of the world, park by the Montauk Lighthouse and drink in the 360 views of the eastern tip of the island.

People come from everywhere to see the Montauk sunset
Montauk sunset (©Meryl Pearlstein)


Montauk has a mix of 50s-type motels, updated with today’s conveniences, new décor and resorts. Known by music fans, The Rolling Stones captured the feeling of the dive-y Memory Motel in their song by the same name on their “Black and Blue” album. Marram Montauk is an updated boutique hotel that caters to a younger, hip set with beach access for picnicking, biking and fire pits. Gurney’s Resort has a choice of cottages, suites and room, plus a spa, an outdoor cocktail bar, the acclaimed Scarpetta Beach restaurant and a schedule of wellness classes.

Gurney's Resort has an expansive beach area
Gurney’s Resort  (©Meryl Pearlstein)