Where to Dig Into Lobster Rolls, Take a Beach Hike, and Party in Montauk

This famous fishing town outside of NYC is surprisingly cool.

Montauk, New York | haveseen/Shutterstock
Montauk, New York | haveseen/Shutterstock

Montauk, once most popular among fishermen and surfers, today, offers an eclectic mix of parties, share houses, live music, breweries, lobster rolls, and, yes, still some of the best fishing and surfing in the Northeast.

About 120 miles from NYC, Montauk is accessible by train, but I prefer to spare myself the Hunger Games-like madness that ensues at Penn Station on a Friday afternoon and hit the road instead. For this trip, I rented a car from Turo, which is essentially an Airbnb for car-sharing, because I’d take the Hamptons traffic over the Long Island Rail Road’s crowded train cars any day.

After tackling the Long Island Expressway, you’ll find yourself on the appropriately named Montauk Highway, a.k.a. Route 27. Take a moment to admire small towns like Bridgehampton and East Hampton, each offering a mix of name-brand stores, local designers, and eateries. Stop for a bite to eat at TownLine BBQ in Sagaponack, Goldberg’s Famous Bagels in Southampton (the best bagels in all of New York, I swear it), or Carissa’s the Bakery in East Hampton.

Travel time:

4 hours from NYC by car.
3 hours from Penn Station on the Long Island Rail Road.

If you don’t do anything else: Lobster rolls in Montauk 

The most important stop you’ll inevitably make is for a lobster roll, and there’s a plethora of popular spots to choose from. So many, that some people even engage in lobster roll crawls.

In fact, you may overhear heated debates on who has the best one. Is it Bostwick’s Chowder House? The Clam Bar at Napeague? Someone will likely confidently pronounce The Lobster Roll (a.k.a. Lunch) as the winner. Personally, I’m Team Clam Bar, but, really, you can’t go wrong with any of them.

Ditch Plains Beach
Ditch Plains Beach | rj lerich/Shutterstock

Fill the weekend with: 

Things to do outdoors in Montauk

First stop: the beach. If surfing (or watching other people surf) is your thing, make your way over to Ditch Plains Beach for Long Island’s best waves—just remember the summer crowds will be out to play as well. If relaxation and convenience is more your speed, head to Kirk Park Beach, which is within walking distance of Montauk’s charming downtown. Here you’ll find sunbathing summer renters and weekend warriors discussing what hotspot they’ll hit that night. For a beautiful beach hike, check out nearby Camp Hero State Park.

Local museums in Montauk

If it’s your first time in Montauk, consider driving out to The End (yes, it’s quite the literally-named destination) to check out the famed Montauk Point Lighthouse commissioned by George Washington’s administration. Take a look inside and check out the lighthouse’s museum to see letters signed by Thomas Jefferson as well as preserved maps of Montauk from the 1800s. Down the road you’ll also find the Carl Fisher House, which hosts lectures and exhibits on Montauk’s history, and the Montauk Indian Museum, where you can learn about the Indigenous tribes that originally settled there.

The Surf Lodge
Photo courtesy of The Surf Lodge

Nightlife in Montauk

For such a small beach town, the nightlife options in Montauk are abundant, with everything from bougie hotel bar scenes at Gurney’s Montauk Resort to local dives like Shagwong Tavern. Check out The Surf Lodge, a restaurant/hotel/live music venue that is attracting amazing talent this summer with acts like Anderson .Paak as DJ Pee .Wee and BLOND:ISH. For more tunes, The Montauket is always a great place to catch local bands accompanied by a killer sunset. And I’d be remiss not to mention Memory Motel, the famed dive bar and motel made famous by The Rolling Stones song of the same name.

Eat, drink, and sleep:

Restaurants & bars in Montauk

Pregame dinner with a visit to Montauk Brewing Co. for the East End staple Summer Ale before heading out to one of the many Montauk dining spots you’ve probably scrolled through on Instagram. There’s Harvest on Fort Pond, which serves amazing Italian cuisine featuring local produce and seafood, and the Crow’s Nest, for chill vibes and craft cocktails. For even more fresh seafood, there’s Inlet Seafood, Duryea’s (get the famous Lobster Cobb Salad), and Gosman’s, just to name a few. No matter where you choose, a good meal should always end with soft serve from John’s Drive-In.

Gurney's Montauk Resort & Seawater Spa
Photo courtesy of Gurney's Montauk Resort & Seawater Spa

Where to stay in Montauk

The increasing popularity of Montauk means there are more choices in accommodations than in most other Hamptons towns. One of the largest (and possibly priciest in peak season) is the aforementioned Gurney’s. This resort-style hotel has a seaside version of Manhattan’s popular Scarpetta restaurant just off the lobby as well as a private beach and recently renovated Seawater Spa boasting a bath house and IV Drip Lounge. There are many other cheaper hotel options to choose from, as well as beach motels, but in the summer months, none of these will come that cheap. Weekend rentals are also a smart way to go—just fill the house with a bunch of friends hankering to escape the city.

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Helena Fistel is a Supervising Social Producer at Thrillist.