Cultural Experience | New York

Meet Me in Montauk

Montauk City Guide

Located on the eastern most point of Long Island, Montauk was once a summer pastureland for cattle, sheep and horses during the end of the 1600s to 1700s. From then, it grew into a sleepy fishing town (still is, at its heart), and today, visitors come here to experience the Hamptons without the pretension. Anyone that has visited Montauk knows that there’s a certain type of magic that happens here – visit once and you’ll always want to return.


What to do

• Montauk Point Lighthouse

The Montauk Point Lighthouse is a National Historic Sight, the nation’s fourth oldest active lighthouse, that offers sweeping views of the Atlantic Ocean. Visitors can visit the museum ($10) that exhibits maritime artifacts and historical documents and climb the 137 steps to the top for an even more impressive vantage point.


• Second House Museum

Montauk’s Second House Museum is a treasure. Standing as the oldest structure in Montauk, Second House provides visitors a glance back in time to the agrarian customs dating back to the 1660s – when the area was solely used as pasturelands. Today, perfectly manicured lawns surround the grounds, as well as fragrant rose gardens to stroll though. During the summer, the museum hosts craft fairs, movie nights, and even doggie socials!

• Ditch Plains Beach

Ditch Plains is considered one of the top surfing spots on Long Island for the experienced and beginners alike. Take advantage of the long breaks and catch a surfing lesson, go for a long walk or play in the tide pools – this beach has it all. Be on the look out for the Ditch Witch food truck for the best beach food in town.

• Deep Hollow Ranch

Break out the boots and explore the coastline on horseback. Deep Hollow Ranch can arrange a trail ride through pristine beaches and countryside guided by true cowboys (and cowgirls!) – western saddles only!


• Sail Montauk

It’s time to learn a new skill! Sail Montauk offers private, group, and workshops to individuals that want to learn how to sail or brush up on their skills. Along with lessons, Sail Montauk’s very own S/V Mon Tiki catamaran offers 2-3 hour, day or evening sunset cruises for those that just want to enjoy the ride.

• Day Trip to Block Island

Just one hour by high-speed ferry, lies Block Island. Boasting a casual atmosphere similar to Montauk, visitors can rend a bike, go on a guided tour or rent a moped to explore the island.


Vintage lovers rejoice at Melet Mercantile. The warehouse sells a collection of vintage clothing, accessories, maps, books and everything interesting. Bob Melet, the owner, was once a vintage buyer for Ralph Lauren but has since turned his passion into a vintage hunter’s paradise. 

Fun for Free

There is no better day than one spent surrounded by nature. For a day of free fun, hike the trails in Camp Hero State Park. The walk is not extremely strenuous and along with the picturesque landscape, there is also history. The 754-acre State Park was formerly a military base; some bunkers, buildings, batteries, and an old radar building still remains – these military installations are what inspired the Netflix series, Stranger Things (Montauk Project).


What to Eat

Eat here:

• Swallow East: Easily one of the best restaurants in Montauk, Swallow East has a casual-chic atmosphere and provides elevated libations, and comfort food – tapas style. During the summer guests can catch live reggae music.

• La Brisa: Tacos made with homemade tortilla, what more can you want? Casual dinging without the compromise – they also serve scrumptious drinks made with fresh squeezed juice.


• South Edison: Casual dining with upscale farm-to-table dishes is offered here along with eclectic décor. You can’t go wrong here – everything is delicious!

• Harvest at Fort Pond: Harvest offers up Tuscan-inspired dishes served family style. Situated on Fort Pond, Harvest will provide you with gorgeous, jaw-dropping sunset views.

• 668 The Gig Shack: An array of comfort foods with a twist, plus live music!

• Naturally Good: Anything your healthy heart desires. Along with smoothies, fresh juice, and a small menu of good-for-you breakfast and lunch options, they also have a small grocery store where you can stock up for picnics.


Try this:

• Asparagus fries at Swallow East

• Acai smoothie at Happy Bowls

• Lobster Roll at St. Peter’s Catch

• Tuna Salad at Naturally Good

 After Dark

Ruschmeyer’s: Low-key ambiance with a magical garden filled with lanterns, and fire pits for cool nights.


• Surf Lodge: Always a party but uniquely its own with laid-back vibes. Check out their schedule of bands on the weekends and be sure to make reservations.

• Liar’s Saloon: Nothing pretentious about Liar’s, notably a local’s bar, the prices can’t be beat.

• Memory Motel: Memory Motel doesn’t usually draw a crowd until the late night hours – kegs in the parking lot, what can go wrong?

• Sloppy Tuna: If you want to party like you’re in college, this is the place.



There are several ways to get to Montauk from NYC:

• Train: The Long Island Rail Road has scheduled trains that make the trip to Montauk daily. Check out the website for fares and schedules as they range depending on time.

• Bus: The Jitney offers reasonably priced fares and a seamless way to the Hamptons.

• Car: The drive can be done in two and a half hours and it erases the worries of unplanned track work on trains or unexpected bus breakdowns. Having a car to drive around down will also save on cab fares in the long run.

While in Montauk, cabs are everywhere and will run you about $5-$6 per person depending on your destination.

Local Knowledge

Although Montauk is known for its beaches and great restaurants not many realize that it is surrounded by over 70 acres of preserved land and boasts an insanely diverse assemblage of habitats so there are countless trails to explore.

There are a plethora of wineries near Montauk – perfect for a day trip when you don’t feel like going to the beach.

Don’t skip out on any bonfire parties!

Montauk City Guide

Nika Hedrick

Fashion Institute of Technology | 4 stories

Nika is an Advertising and Marketing Communications major with a minor in Art History. Her love of travel goes back to the roots of her upbringing on the resort island of Phuket, Thailand where she went to an international school. Beyond travel her numerous passions include food, art, photography, reading, writing and NYC, where she currently resides.

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