Road Trip: Manhattan to Montauk

Lobster rolls, sunset parties and other classics along the way to NY's easternmost point

by Mike Tommasiello

Each summer, when the heat and humidity in the city reaches unbearable levels, many New Yorkers set their sights on an escape. A particular favorite is easternmost point of the state: Montauk. Beaches, surfing, clams, beer, lobster rolls, and more—Montauk used to be known as the anti-Hamptons, though has certainly been gaining popularity over the past decade.

Accessible by the Jitney, train or car, the trip itself can be quite the odyssey—especially on a Friday. We took the 2018 Maserati GTC (with a convertible top, of course) on our recent weekend in Montauk, and despite the traffic—which can make the drive some five or six hours—it was an incredibly fun choice. The car’s commanding 454 horsepower came into action just a couple of times; while in contrast the impressive sound system was on the entire time—offering crisp sound quality no matter the genre. Since the drive can be long, we also stopped off at a few places on (and out of) the way, making what could have been an arduous journey, and entirely adventurous one.

Harbor Market & Kitchen

During the long journey, our first stop was to Harbor Market & Kitchen, located in Sag Harbor, about half an hour out of Montauk. With the sheer volume of farms in the region, enjoying some farm-to-table fare is essential. While the stretch from Westhampton to Montauk can be known for pricey meals, Harbor Market & Kitchen offers excellent artisanal small bites, sandwiches and salads at reasonable prices. From fish tacos to tasty breakfast sandwiches, there are plenty of options to fuel the rest of your drive.

EMP Summer House

Make sure you have a reservation (you’ll need a credit card to do so) for Daniel Humm and Will Guidara’s Eleven Madison Park Summer House pop-up, EMP Summer House. Located right outside of Montauk in East Hampton, the pop-up is serving dishes made from fresh produce sourced from local farmers and producers. For a snack, try a bunch of the spreads

with wood-fired bread and one of the many refreshing cocktails. Stick around to play corn hole and other games in the backyard at this venue that feels more like a high-end BBQ than a world class restaurant—which is exactly why it’s so appealing.

Lunch / The Lobster Roll

Don’t let the name (or names) fool you, Lunch, a cozy restaurant off the beach right off Old Montauk Highway serves far more than they advertise. One of the region’s most storied institutions, the restaurant is technically named The Lobster Roll, but locals began to affectionately refer to it as Lunch given the prominent sign. As if the name wasn’t a dead giveaway, the lobster rolls here make the spot an absolutely essential stop, but there’s plenty more—from chowder to fish and chip, salads and more.

Montauk Point

Switching off your phone, and taking a seat on rocks by the beach is perhaps the best way to mentally unwind on a weekend escape. With unparalleled views of the water, Montauk Point is a Long Island icon and one of the best national parks the state has to offer. No trip to Montauk is complete without experiencing the easternmost point in the state, breathing the fresh air and truly appreciating the fact that you’re far away from the city.

Surf Lodge

Our final stop was the chill but sophisticated Surf Lodge. If you plan on visiting, be prepared to wait in line—thanks to its combination of location and atmosphere, it’s wildly popular. A covetable spot, it’s nestled perfectly on the lake which makes for stunning sunsets, not to mention they always have musical talent performing. During our visit, James Murphy was playing a set for their sunset party. Be sure to check online for their summer program, which will continue into September.

Hero image courtesy of Surf Lodge, Harbor Market and Montauk Lighthouse images courtesy of respective venues, all others by Cool Hunting