Nostalgic Montauk: In search of summer dining traditions

Past the glitz and glamour of the tony Hamptons lies Montauk, a once-sleepy fishing village determined to retain its charm. Formerly the stomping grounds of Teddy Roosevelt, and before that, a vast wilderness overseen by the indigenous Montaukett people, this easternmost point of Long Island — and of New York State — evokes a trove of delightful childhood memories for me. Seemingly endless family vacations were spent fishing off pristine Long Island beaches, coveting salt-water taffy from the candy shop at Gosman's Dock, watching yachts make their way in and out of Westlake Marina, learning how to eat a lobster.

It’s changed in the 40 years I’ve been making the trip, first as a child, then as a teenager discovering the simple pleasures on her own. As a carefree 20- and 30-something, I rented summer houses with friends, and now, as a parent, I yearn to give my daughter her own sweet summer memories. Today, Montauk is shinier, full of brand label-wearing sun-chasers, many seeking a rung in the hierarchy of summer society. But if you look closely, shrug off the sparkle and stick to the classics, you can still bask in yesteryear’s summer glow.

My body starts to decompress and the day warms just as I spy a promise of sustenance — the sand-speckled red, white and blue sign announcing “Lunch,” a.k.a. Lobster Roll restaurant — which comes into view on the south side of Montauk Highway.

Here, most tables are graced with the namesake dish, whether the mayo-based classic Maine roll, rustic-looking and served cold, and or the more sophisticated Connecticut-style roll, served hot and slicked with butter.

A mainstay of the Montauk community since 1965, Lobster Roll has been owned by the same group for the past 40 years and retains its sea town allure. Settle inside or out for your lobster roll alongside a generous portion of crinkle-cut fries and call it “lunch.”

A little beach time, a well-deserved nap and, before you know it, it’s time for one of Montauk’s famous sunsets. There are few better places to admire the bursts of color — pinks, reds, oranges and purples — than at The Montauket. This out-of-the-way dive, around since the 1920s and family-owned since 1959, features just-right bar food, cheap beers, and a view overlooking Fort Pond Bay. You won’t see any kitten heels in The Montauket; instead, this is a dusty flip-flop kind of place where Bud Light trumps the espresso martini and local live music lights up the crowd. Stay for staples such as fish-and-chips, a burger, fried fish platter or sesame-crusted tuna salad. Or if you feel like jumping into the deep end, head over to The Dock.

“No stupid people, no yapping mutts, no sensitive drunks, no screaming kids, no strollers, no cell phones,” reads the signage outside of the door of this beloved spot that prides itself on its disdain for summer renters — and tourists in general. Locals, though, know to go for some of the best burgers and fresh fish around, and, in season, soft-shell crabs. Fittingly, it was a handshake deal over shots of blackberry brandy that sealed the sale of the restaurant by the Fitzgerald family to the Watson family, who has owned The Dock since 1973. Here, the games are always on, the crowd is always lively and the people-watching is always worthwhile. Eat, drink and follow the rules (cash only, by the way) and you’ll be just fine.

On any first full morning in Montauk, I head directly to Joni’s for a breakfast wrap and iced coffee. With its surf maps of Hawaii and California and menu of organic options — owner Joni Brosnan was a vegan when she opened in 2001 — it’s here that the egg wrap took hold of my heart and never let go.

You can customize from a roster of ingredients; a combo of egg whites, Cheddar, caramelized onions and mushrooms, spinach and Joni’s requisite hot sauce is my go-to favorite. With only a few picnic tables outside and a communal center table within the cozy, cute shop, the move is to call ahead and order to go.

Fried chicken is the beach lunch of champions, and they make it fresh all day long at Herb’s Market, an old-school establishment with a somewhat cranky reputation. That doesn’t stop the masses from flocking to the back steam counter on summer mornings for golden, piping-hot drumsticks and wings, juicy thighs and/or meaty breasts, all crusted, crisped, perfectly peppered—and ready to be loaded into foil warmer bags for irresistible midday munching.

After a day at the beach, I roll straight into Westlake Fish House at Westlake Marina, home to more than a dozen charter boats and 100 slips. The Fish House—a 60-plus-year-old family business—was sold in 2023 yet still maintains a down-to-earth yet buzzy energy, strong cocktails, a vibe that appeals to local fishermen (both commercial and recreational) and some of the freshest catch around. At this low-key, always-a-wait (no reservations) throwback, the interior back bar—complete with decades worth of graffiti along the ceiling and a pass-through window that overlooks the outdoor dining on the docks—and no-fuss dining room are homage to Montauk’s origins. Surfcasters and other fishermen come from all over, as it’s still the largest surf and fishing destination in the state.

The sushi offerings, which have become a draw, are the only au courant part of the establishment. Try the MTK roll (spicy tuna inside; tuna and fluke outside), the Westlake (avocado, spicy tuna, shiso inside; fluke and sea bass outside) or The Tank (pepper tuna, avocado inside; yellowtail and salmon on top). Purists can find a piece of beautifully cooked local fish. Kids go crazy for the massive mac-and-cheese. Watch the boats come in and the fishermen weighing and filleting their catch off the side of the restaurant, listen to live music on weekends and allow yourself to linger. I promise, this is the spot. 

There’s a kind of innocence about entertainment in Montauk that will encourage parents — and kids — to put down their smartphones and heave a giant sigh with relief without knowing exactly why. At the laid-back Montauk Brewing Co., grabbing a beer on the patio means that you can overlook the baseball diamond where kids play long after the sun sets, parents looking on. Fans of the brewery, which originated in a local basement 13 years ago, will be interested to know it will be expanding its footprint westward; it’s scheduled to open in the former Port Jefferson Brewing Company this month.

And John’s Drive-In, a no-frills burger and ice cream joint now owned by David and Maureen Rutkowski, is the sort of place that haunts my dreams all winter. A vanilla soft-serve with rainbow sprinkles, which was ten cents in 1967, when John’s opened its doors, is now $6.50, and still worth every penny. There are hand-scooped flavors listed in abundance above the soft-serve machines; a greasy (but delicious) fast-food menu encompassing hamburgers and fries, fish-and-chips and onion rings with an aroma that fills the air. There’s always a line, longest in the glow of sunset, after families have finished their suppers, or wrapped up a fierce round of miniature golf next door at Puff ’n’ Putt. This is summer at its most simple, most authentic and most evocative. What flavor to choose is the most pressing problem you’ll face.

Unless, of course, you are trying to decide whether to book a surfing lesson or two at East End Surf Club, on renowned Ditch Plains Beach. A trip to Montauk isn’t complete without at least stopping by the beach, where the surfers gather and glisten each morning as the tide comes in. Lithe, energized shadows carrying oversized boards jump out of the truck bed of mud-spattered pickups with license plates like “Surfari”; a few shimmies and they’ve found their way into wetsuits. One by one, they paddle out for a shot at the day’s first break. The ocean’s varying palette — green, brown, blue —rollicks and rolls in the morning light. Beat me, the water seems to say, and each Ditch player accepts the challenge.

Whether you are surfing or sunning, from Friday through Monday since 1994, the Ditch Witch food truck has been feeding hungry bellies with favorites ranging from egg wraps and cinnamon buns in the morning to sesame noodles, poke bowls, wraps and burritos at lunchtime. This spot opened by local mom Lili Adams is now run by her kids, Grant and Abby Monahan. Practically a culinary rite of passage when in Montauk, the daily specials, items like ahi tuna katsu, never disappoint.

The beauty and the curse of today’s East End lie in the tension between — and peaceful coexistence of — night fishermen and Wall Street billionaires, farmworkers and fancy ladies who lunch, dockworkers and boat slip owners. The high-low dynamic of the unfussy, layered hamlet of Montauk is part of its draw, much to the chagrin of locals. But it’s hard to ignore. And, admittedly, having some lush options in the mix means that splurge-worthy occasions are now a little splurgier.

The Surf Lodge, which opened in the summer of 2008, may have been the clearest indicator of things to come for Montauk’s locals-only vibe. Evenings at this breezy bayside perch that offers Fort Pond sunset views, live music and the ultimate alfresco lounge, eventually attracted scores of weekend revelers looking for a new party palace. Locals visited on Sunday nights, after the chaos had departed, for live jam sessions that spilled into weeknights.

This was the first real “Montauk scene” and there’s still something deeply attractive about it. The food — which changes direction regularly and at this writing is offering a tone-deaf $150 Popeye’s chicken tender tower — is beside the point. But the cocktails always flow, the beer is local and cold, and the chill Montauk essence returns to remind residents that, ultimately, this is their town.

If you are in the market for good, perhaps overpriced (you decide) food with your scene, off to Duryea’s you should go. This former family-run fish market founded in the 1930s evolved into something of a BYOB picnic spot for some of the best lobster on the East End. In 2014, billionaire financier Marc Rowan bought Duryea’s Lobster Deck and wholesale fish market and gave it new luster.

Now white-washed, its pier stretching out into Fort Pond Bay, the restaurant retains its simple lobster-shack roots, but with a sassier price tag and divisive cult favorite dishes like the lobster Cobb salad for a whopping $97 (meant to be shared, it easily serves two or three). Wait for a table with some rosé in hand, then order up your shellfish feast at the counter and take in the view. If you enjoy fresh fish, spring for the impressive daily whole fish preparation (MP), served family-style and, to my mind, the best thing on the menu.

While Gosman’s Dock, once a standby, has changed hands multiple times over the years — it currently houses an outpost of Manhattan’s clubby Bagatelle—the best of the glossy alfresco spots is The Crow’s Nest, a romantic, twinkly, picturesque cottage hotel and restaurant that bathes in the sunset over Lake Montauk.

Spread out over a small hill, at the top is a sprawling lawn, bordered by interconnected terraced patios for evening dining. Here are Mediterranean dishes from beetroot hummus, Montauk tuna in various preparations, lamb or swordfish kebabs. There is always a shellfish pasta on the menu — blue crab linguine or lobster tagliatelle, perhaps. Don’t skip it. 

At the bottom of the hill is a waterfront spot where you can sip wine while you wait for your table (The Crow’s Nest doesn’t accept reservations) and contemplate a future visit to nearby Deep Hollow Ranch, America’s oldest cattle ranch (beach and trail rides; pony camp), and the 1797 Montauk Point Lighthouse (360-degree views, live webcams and Brandi Carlile in a benefit concert in late July).

I allow for a last-morning breakfast fling at one of the Island’s oldest bakeries, Montauk Bake Shoppe. Here, I’m talking the fried jelly croissant, which eats like a cruller, vertically, each bite equal parts jelly and flaky, deep-fried croissant. Just off the main promenade in the center of town, the humble, busy Bake Shoppe (est. 1969) has been making jelly croissants for more than 30 years, predating Dominique Ansel’s Cronut, which debuted in Manhattan in 2013. “We sell between 900 and 1,500 of them per summer weekend, maybe about 500 to 600 during the week,” said longtime store manager Aftab Ahmad. The shop preps over 2,000 a week, because “we don’t want to run out and disappoint anyone.”

Any time I spend in Montauk ends with a stop at the Clam Bar at Napeague, which is marking its 45th anniversary this year. It’s now owned by local couple John and Kelly Piccinnini, who also own nearby Sett Coffee. (They also recently took over Sag Harbor’s Corner Bar.) In the shade of a yellow-and-white umbrella, it’s here’s that I soak up my last moments over clam chowder — Long Island style, obviously, half white, half red — fried clams, local corn on the cob and a lemonade. If you’re a lobster-roll-with-mayo fan, the Clam Bar is your nirvana, but mine is the lobster BLT. Take a piece of Key Lime pie to go.

Sated and sun-drenched, kissed one last time by the salty air, I roll down my windows, turn up the Grateful Dead and hit the road. Same time, next year.