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It’s during the pre- and post-season, when the vintage 4x4s and surfboards are safely back in Brooklyn, that Montauk is at its purest and perhaps finest

On any given summer weekend, the easternmost town on Long Island can feel like a beachside outpost of NYC’s downtown scene. But Montauk is still very much a working fishing town, with all the grit—and the hidden gems—that that entails. Photographer and blogger Matt Hranek takes a deep dive.

t the tip of the peninsula on Long Island’s southern shore, some two-and-a-half hours (without traffic) from New York City, you reach The End, the easternmost town in the state of New York: Montauk.

It’s an area of intense natural beauty: inland lakes, pine forests and endless stretches of duned beaches. It’s also a place rich in American history, once home to the Montaukett tribe (from which it gets its name). Teddy Roosevelt’s Rough Riders took R&R on its shores after the Spanish-American War, and rumrunners found refuge there during Prohibition. Later it became a summer escape for artists, like Andy Warhol, and surfers, who rode the break at Ditch Plains. More recently, it has become the de facto eastern outpost of New York’s nightlife scene. But first and foremost, Montauk was—and is—a working fishing town.

And while there’s no better place on the South Shore to spend a summer weekend (sorry, Amagansett, you’re a close second!), it’s during the pre- and post-season, when the vintage 4x4s and surfboards are safely back in Brooklyn, that Montauk is at its purest and perhaps finest—inhabited and repossessed by the locals and the fishermen that live there year-round. The beaches are virtually empty, the bars and restaurants are welcoming and the area is yours to explore.

The scene at the docks—first and foremost, Montauk was and is a working fishing town


Here’s one man’s take on the ultimate Montauk itinerary—equally relevant for spring, before the crowds come, or the height of summer, when you need a break from the scene. Just remember: Book your hotel early no matter when you plan to go; even the off-season can be tricky due to limited space. I like the Montauk Yacht Club for its unfussy rooms and relative proximity to the action. Or, if you want to be right on the beach and enjoy the spa experience, try Gurney’s. After May 1, it’s tough to beat the Crow’s Nest from Sean MacPherson—the urban-boho guru behind the Maritime, Bowery and Marlton—or Ruschmeyer’s, the laid-back retreat located at a former summer camp and co-owned by a former Surf Lodge guy. There are a few additional recommendations below.


8:00 P.M.
An 8 o’clock arrival means you’ve been on the road for a good three-plus hours, factoring in Friday afternoon traffic. Check in to your hotel and grab a bite and a drink. If your stay includes the Montauk Yacht Club, there’s not far to go: The hotel’s open-air Barracuda Bar is relaxed and good for a restorative cocktail and some duck sliders. Or, if you want to stretch your legs, take a 10-minute stroll to the Westlake Marina just down the road. There, tucked into the boatyard, you’ll find the Westlake Fish House, a favorite of local fishermen and weary city travelers. But go easy—you’ve got a busy day ahead.


8:00 A.M.
No matter when you’re here, your first morning in Montauk should always begin with a good beach walk. But first, fortify yourself with a coffee and hearty breakfast at Joni’s Kitchen. Just south of Main Street, Joni’s is open all year and a favorite spot for the surf set. Order any of the breakfast wraps or grab some homemade banana bread, and then head to Ditch Plains beach to watch the surfers. Make sure and leave some time to head to Camp Hero, a decommissioned military base turned state park that’s home to great hiking trails and views, all surrounded by radar towers, abandoned bunkers and more Cold War relics. Surreal and as awesome as it gets.

Homemade banana bread at Joni’s: the perfect way to start a long day of exploring


11:00 A.M.
In season, the local outpost of Melet Mercantile, on Industrial Road, is not to be missed. Owner Bob Melet is best known for his epic collection (and curation) of vintage clothes and antiques, which has been inspiring designers, editors and collectors in his NYC showroom since 2003. Each summer, Bob reimagines the “outpost” (actually a storage unit in a mini mall) with a thoughtful and well-styled edit of gear, books and bric-a-brac.

1:00 P.M.
There’s no better introduction to the true local scene than lunch at the Dock, a Montauk Harbor mainstay since the 1970s. Owner George Watson, who’s usually behind the bar, has the best pedigree of any bar owner I know: He’s a military vet, former FDNY fire lieutenant—and a boxer. The beer is cold and free-flowing, and the food is amazing (try the steamed mussels or lobster). The place is brimming with character and is all very Instagram worthy, were it not for the Dock’s strict no-cell-phone policy. Infringe and you’re likely to be put back in line by a blast of George’s bullhorn from across the bar.

Iconic signage at Montauk mainstay the Dock


2:00 P.M.
After lunch, take a stroll around the docks and poke around the fishing boats before hopping on a fishing charter (if the weather permits). I’ve heard good things about the charter Sea Wife IV from my fishing buddies. Because of Montauk’s geographic location and proximity to deep waters, the tuna, striped bass, bluefish and blackfish seasons are epic right off its rocky shores. (If you’re lucky enough to be in town for the fall run of striped bass, book a fly-fishing or light-tackle trip and fish the “blitz” with my good friend Bryan Goulart at Point to Point Charters.)

5:00 P.M.
Celebrate your return to dry land—and, one hopes, haul of fish—with a cocktail at the Shagwong. Established in 1969, the Shagwong—which is on Main Street and is marked with a glowing neon sign—is a Montauk institution and another local favorite. You will always find a mixed bag of locals and travelers at the bar, and it’s one of those rare places that braves the four seasons.

The charming interior at the Shagwong, where you’ll always find locals and travelers at the bar

It’s all very Instagram worthy, were it not for the Dock’s strict no-cell-phone policy. Infringe and you just might be put back in line by a bullhorn blast from across the bar.

8:00 P.M.
Come dinnertime, where you eat will depend heavily on when you visit. In summer, you’ll want to hit the restaurant at the Crow’s Nest, which serves up local seafood (scallops, fluke crudo) with the occasional South Asian twist (vegetable curry, chicken kebabs). It’s a short walk from the beach at Ditch Plains and exudes the kind of cozy, unstudied (yet meticulously calibrated) charm you expect from MacPherson. Before May, however, it’s about eating where the locals eat, so head to the Seawater Grill at Gurney’s. Take a break from all that seafood and indulge in a Tomahawk pork chop or the grilled skirt steak. Weather permitting, dining oceanside by a fire pit is a must.


9:00 A.M.
Any time of year, you’ll want to start your second day with an old-school diner-style breakfast at John’s Pancake House. John’s is open all year and serves great coffee and perfect pancakes as well as other diner mainstays like over-easy eggs and home fries. Grab your paper, settle in and plot your second day.

Grab the paper, settle in and plot your second day over a diner-style breakfast at John’s


11:00 A.M.
Head over to the Montauk Lighthouse in Montauk Point State Park. It’s the oldest lighthouse in New York State and the fourth-oldest active lighthouse in America. The views are spectacular, and there are great spots for hikes and beach walks all around—perfect to work off those pancakes.

Montauk’s iconic lighthouse. No trip is complete without a visit.


1:00 P.M.
Take a short drive toward the town of Amagansett and head to Napeague Bay sound, where you’ll find Multi Aquaculture, a great little fish farm that does amazing takeaway meals—their lobster bisque should not be missed—at its on-site shop. You can call ahead and order, or if it’s nice enough, eat at one of its outside tables.

3:00 P.M.
On your drive back, look out for the Deep Hollow Ranch, which dates back to the 1650s and is the oldest operating cattle ranch in America. It’s also where Teddy Roosevelt and his Rough Riders set up Camp Wyckoff after their victories in the Spanish-American War. It offers beach and horse-trail riding year-round.

Yes, the nation’s oldest working cattle ranch really is on Montauk—and it has played host to everyone from Teddy Roosevelt’s Rough Riders to the waitress’s family on The Affair


5:00 P.M.
After that, you’ll find yourself drawn back to the Dock. Don’t bother resisting. There’s no better way to ease the saddle sores than with an ice-cold beer and another visit with your newfound local friends (and trust me, you will make friends there).


8:00 P.M.
End your visit a stone’s throw away from the Montauk Yacht Club at Dave’s Grill, another Montauk classic. Located on the harbor, it’s the perfect place to round out your immersion in the local scene with a menu that stays true to local form—try Dave’s original cioppino and the butter-poached-lobster roll. Note: It books up quickly, so make a reservation. Or if you’re here in season, book a table at Ruschmeyer’s, where the gang from one of my favorite New York restaurants, the Smile, handles the menu heavy on—what else?—fresh local seafood.


Montauk Yacht Club Resort & Marina
32 Star Island Road

Gurney’s Montauk Resort & Seawater Spa
290 Old Montauk Highway

Crow’s Nest Inn
4 Old West Lake Drive

161 Second House Road

Barracuda Bar at Montauk Yacht Club Resort & Marina
32 Star Island Road

Westlake Fish House
352 West Lake Drive

Joni’s Kitchen
9 South Edison Street

The Dock
1 Montauk Harbor

774 Main Street

Crow’s Nest Inn
4 Old West Lake Drive

John’s Pancake House
721 Montauk Highway

Dave’s Grill
468 West Lake Drive

161 Second House Road

Camp Hero State Park
1898 Montauk Highway

Sea Wife IV at Viking Landing
458 West Lake Drive

Point to Point Charters
Star Island Marina

Montauk Lighthouse
2000 Montauk Highway

Multi Aquaculture
429 Cranberry Hole Road

The Deep Hollow Ranch
10 Old Montauk Highway

Melet Mercantile
102 Industrial Road


Photographer Matt Hranek shoots regularly for Bon Appetit, GQ and Condé Nast Traveler and served as host of Alternate Route on the Esquire Network. Hranek chronicles his adventures on his blog and via Instagram and splits his time between Brooklyn and a 130-acre farm in the Catskills.

  • All photographs by Matt Hranek
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