Follow Montauk Highway to its oceanfront end for a weekend that’s both rustic and refined
Mick Jagger famously stayed longer than he’d meant to in Montauk, partying at the Shagwong Tavern and writing song lyrics. New York clothing designer Cynthia Rowley planted sea grass on the roof of her storefront next to the old Memory Motel and hosts an annual surf camp. And Beyonce and Jay-Z joined the Hamptons’ crowd several years ago, buying a beachfront mansion in East Hampton.
The draw is real at the centuries-old whaling town and former military outpost. Celebrities, surfers, and city dwellers seeking ocean air all flock here, following Montauk Highway across Long Island to its outermost reaches. The hamlet of Montauk, with about 4,000 year-round residents and a name derived from the Native Americans who lived here, is truly at the end of the road—on a peninsula that juts into the Atlantic. Dubbed Montauk Point, it culminates with the iconic, octagonal lighthouse that’s been a flashing beacon on a windy bluff since George Washington was president.
This trip is a joyride I’ve been wanting to take for a while. About 100 miles east of Manhattan and with no skyscrapers in sight, the Hamptons and Montauk are famously a summer-fall escape by the shore—picturesque, super stylish, and salty all at once. A-listers aside, I have a personal connection to the less-flashy history of easternmost Long Island. My New York-born mother would road-trip here on weekends in the 1960s, and my bayman uncle worked on boats, including some from Montauk Harbor. All of my life I’ve been captivated by their old family photographs at Montauk Point and the Lobster Roll seafood spot, aka “LUNCH,” on Montauk Highway.
On a Friday this spring, photographer Peter Frank Edwards joins me on a two-hour, direct flight on Breeze Airways from Charleston to the airport in Islip on central Long Island. Eager for a long weekend of preseason exploring, we pick up a rental car and start driving east toward Southampton, Bridgehampton, East Hampton and, finally, after the road narrows to two lanes and the scenery grows wilder by the mile—to remote Montauk, otherwise known as “The End.”
Our unassuming Toyota sedan weaves into the flow of traffic with Land Rovers and Range Rovers, Porsches, G-wagons, and vintage convertibles. Although eager to get to Montauk, we’re in no rush on the 70-mile drive. I want to take it all in, and soon we make a first stop at an interior design shop recommended by New York friends. English Country Home in Bridgehampton is chockablock with new stock and select antiques—furniture, mirrors, even vintage pond yachts from England—and seemingly every square foot of the ceiling is hung with chandeliers. Wearing bright, blue-rimmed glasses, founder/owner Chris Mead happens to be there, under those chandeliers and not far from the books about flowers, herbs, and gardens that he photographed in the 1980s. Originally from Kent, England, he explains that he began his career in photography before turning to antiques. When asked, he kindly shares some Hamptons favorites, including the cookies at Tate’s Bake Shop in Southampton, weekend finds at Sage Street Antiques in Sag Harbor, and the specialty trees and garden shop in an 1800s barn at Marders next door.
The tree motif continues at Channing Daughters Winery, where upside-down tree roots are the key feature in the logo and signage—almost like those chandelier shapes. Venture capitalist and wood sculptor Walter Channing Jr, who died in 2015, founded the Bridgehampton vineyard and installed his sculptures of inverted trees among the rows of vines. Many of his creations are still in place on the grounds. We order a sampling of local cheeses and sit outside near the vine rows for a tasting. One of dozens of vineyards and wineries in eastern Long Island, Channing Daughters produces several wines inspired by northern Italian regions—the orange/amber-colored Meditazione is particularly delicious, the hue from contact with a blend of white grape skins during the wine-making process.
Back on the road, Montauk Highway becomes Main Street in Amagansett, a hamlet in East Hampton where there’s a low-key elegance in the lineup of boutiques—airy linens at a local shop named French Presse, dresses in Ulla Johnson, art and handblown glassware at Il Buco Vita (coffee and pastries, too), and bins of LPs to flip through at Innersleeve Records.
We drop into Rowdy Hall for a crock of French onion soup and a roasted artichoke to pull apart and dip into melted butter. It had been a chilly Friday of on-and-off rain showers so this is a welcome, cozy warm-up before we head back out under more of the Hamptons’ interesting trees. Turning off of Main Street, we follow Atlantic Avenue for a few blocks to the beach, passing through a neighborhood of gated driveways, shingled cottages, and charming gardens. The tree trunks seemed to be perpetually bending with the ocean breezes near the tall, circa-1902 Amagansett US Lifesaving & Coast Guard Station—it’s open as a museum in summertime.
Before dark, we drive the last few miles into Montauk and its edge-of-the-world wildness. Deer in pairs or even small herds sometimes dart out from woods that line the highway. (About 70 percent of the land in Montauk is conserved in parks and preserves.) The all-caps “LUNCH” sign is still there on the roof at the Lobster Roll takeout where my mom stopped and leaned against a convertible in the early ’60s. Closer to the central blocks of Montauk, there are bars and seafood shops, tufted sand dunes, rambling mansions, and overlooks toward beaches of rounded stones that roll in and out with the waves.
We’ll stay three nights at Marram, perched directly on the beach a couple of blocks from the main streets for shopping and cafes. The 96-room inn is named for the sea grass growing wildly from the dunes, and the vibe is immediately relaxed and organic—the exterior clad in weathered cedar, minimalist prints by New England-based artist Sean Spellman in every room, and sandalwood-scented bath products by Le Labo. Our second-floor, oceanfront room has a small deck, and on the first night, the wind and Atlantic waves rush and rumble outside. I woke at one point imagining that we were actually on a boat, the thrashing saltwater felt so close. By morning, there’s a calming pink glow to the sunlight streaming down the beach, and in the distance, I see surfer silhouettes on the waves.
Frank and I walk out on the beach in the morning and later venture up to the nearby paths and tall bluffs of Shadmoor State Park to get closeup views of the tumbled, round stones on the shoreline, charred driftwood from beach bonfires, and sand that ranges in color from amber to purple hues. (Ancient glaciers carved Long Island, leaving a rocky shore on the North Fork and tall bluffs above sand beaches with smooth gravel stones in Montauk and the Hamptons along the island’s South Fork.)
Within a few miles’ drive is the Montauk Point Lighthouse, where we meet a friendly local who had just finished a hike on the shore. He recommends that we follow a trail in the 415-acre Camp Hero State Park that’s adjacent to the lighthouse on the southeastern side of the point. “It’s a don’t-miss for a money shot of the lighthouse,” he advises, and he’s right. After a few minutes of walking in the wind and sea spray, we turn to have an epic vantage point of the brown-and-white-striped lighthouse that marks the easternmost point of the state of New York.
Next, we head to sheltered Montauk Harbor that’s rimmed with boatyards, shops, and a few restaurants—all in view of the local fleet of commercial fishing and sport fishing boats. We decide to try for a table at The Dock, a low-slung wooden building a few yards from the lineup of trawlers. It’s early evening, and the place is packed, especially at the bar where there’s plenty to look at on the walls—antlers and ship models; a large painting of a boxing match (a former owner held amateur fights just outside); a sign listing what’s not allowed at The Dock, including “No sensitive drunks” and “No man buns;” and an eye-level portrait of jazz great Miles Davis (he lived and played music in New York most of his life).
In the dim light and lively din of conversation, we order Juicy beers (an IPA on tap from Montauk Brewing Company) and when a small table with candle glow opens up, we feel lucky. We slide in and order a clam feast—tomato-red chowder, baked clams casino, and bowl of half shells on ice. All are delicious, and wanting to stay longer, we order a large Greek salad and a gob of carrot cake to finish. God, I love a quirky dive bar with great food.
(Left) A Shore Thing: Tall bluffs in parts of Montauk create a striking shoreline, where wooden steps lead down to the beach. The only oceanfront bluffs on Long Island, they’re a remnant of long-ago glaciers; (Right) Fishing Village: Montauk Harbor still fills with seafaring boats, returning with fresh-catch fare.
Up early again the next day, I look across our porch to see the waves rolling in smoothly and morning sunlight edged with pink-golden glints. After coffees and croissants by the Marram dunes, we decide to motor tour a bit in the Hamptons. The Parrish Art Museum had caught our attention on the drive in, so we follow the Montauk Highway back in that direction to see “The Art of Food,” an exhibition that had just opened (it continues through June 30) and includes works by Andy Warhol, a Wayne Thiebaud linocut of an orderly sandwich tray, and Sherrie Wolf’s lush still-life oil paintings of flowers and fruit. The permanent collection focuses on Long Island-based artists, and the beamed ceilings and modern shed-style architecture of the gallery spaces (designed by the Swiss firm Herzog & de Meuron) are fascinating to walk through.
The mix of rustic and refined continues as we make our way to another East Hampton hamlet, Sag Harbor, via two-lane roads that wind past woods and small farms. At the natty Baron’s Cove inn and restaurant overlooking the Sag Harbor Cove Yacht Club, a fire is burning in the cozy, wood-paneled lounge. Whale carvings, sailing flags, maps, and dark enamel blues and greens add to the maritime feel. I’m told the cocktail to try here is the pink-hued “Jack Rose,” made with applejack brandy, grenadine, and lemon juice and said to be a favorite drink of author John Steinbeck when he lived nearby in the 1950s and ’60s. (His home is used for writers’ retreats and open for tours on select Saturdays and holiday weekends.) I vow to return sometime for that and the live music offerings here, which a manager mentions can range from Frank Sinatra-style crooners to summery yacht rock.
We also walk along Sag Harbor’s quaint Main Street and check out several of the shops, including the beautifully curated 1818 Collective on Madison Street, where most of the shell-white-painted rooms in the circa-1800 Greek Revival home are furnished as if it’s someone’s stylish, lived-in residence—the contemporary lamps, art, and furniture are available to buy, along with select antiques. We stop into Schiavoni’s Market (picking up some very good bagels in the bakery) and wander down to the marina to see sailboats and motor yachts of all sizes. Another place I’d like to visit on a future trip is the prominent Sag Harbor Whaling & Historical Museum on Main Street. Gleaming white and featuring Corinthian columns and a temple-fronted portico, it now houses exhibits, but was once the grand home of a whaling ship magnate in the mid-1800s.
Back in Montauk, we pull into a parking space near the Montauket about an hour before sunset. Open since the late 1950s, it’s another low-key joint with rustic-cool flair. With a large bar inside that also has a window for walk-up drink orders on the deck, the idea is to get a beer or cocktail in hand and bask in the melon-orange light before sundown. The local Lynn Blue Band is playing songs by Bill Withers, Macy Gray, U2, and Lenny Kravitz, and a group of women in their 20s dance in front—several wearing silk slip dresses and heels with sweatshirts over top, as a warm sunlit glow streams in across the Block Island Sound. It’s a glorious close to what I hope is our first-but-not-last weekender at “The End,” and a salute to summer days to come.
Flight: Breeze Airways (flybreeze.com) offers two-hour, nonstop flights between Charleston International Airport (CHS) and New York’s Long Island MacArthur Airport/Islip (ISP). There’s no “first class” per se on Breeze, but you may upgrade to a “Nice,” “Nicer,” or “Nicest” ticket to include checked bags, for roomier seating, and/or avoid change fees.
Local transport: Booking a rental car helps if you plan to venture between towns. The airport is within a one-to-two-hour drive to locations in the Hamptons, Montauk being the farthest destination. Pro tip: look for lodging that includes free parking and/or offers bicycles for around-town use.
(Left) French onion soup and a Guinness for a cozy lunch at Rowdy Hall, Amagansett; (Right) Historic maps of Long Island at the Restaurant at Baron’s Cove in Sag Harbor.
Taste
Alimentari Beach: Find Negroni cocktails, pizza, pasta, and wine inside or out of the cafe’s curvy walls; open year-round. 752 Montauk Hwy., Montauk; alimentaribeach.com
The Dock: A buzzy crowd of clams and conversation in a wood-paneled saloon at the fishing docks; the changing menu is based on fresh catches. 482 W. Lake Dr., Montauk; thedockmontaukharbor.com
The Montauket: A dive bar with a shorefront deck, live music, cold beer, and a gorgeous sunset view across Fort Pond Bay; 88 Firestone Rd., Montauk; themontauket.com
Rowdy Hall: This new address for a longtime Hamptons tavern serves Bavarian pretzels, French onion soup, burgers, seafood, specialty cheese boards, cocktails, and draft pours. 177 Main St., Amagansett, rowdyhall.com
Schiavoni’s Market: This local market established in 1932 has a full deli and bakery and is an easy stop for snacks and picnic groceries. 48 Main St., Sag Harbor; schiavonismkt.com
Stay
Baron’s Cove: A historic hotel with fireplaces, a cozy nautical feel, and literary cache—it was a favorite of John Steinbeck. There are also wide porches and a pool, and it’s an easy walk to Main Street and the marinas. 31 W. Water St., Sag Harbor; baronscove.com
Hero Beach Club: There’s a swim-surf vibe at this modern refresh of a 30-room motel across from Kirk Park Beach. 626 Montauk Hwy., Montauk; herobeachclub.com
Marram: A beachfront resort with a calming design of natural wood and sea grasses, spacious courtyards, and a restaurant that’s open seasonally (this year through November 24); downtown Montauk is an easy walk or pedal (borrow from the hotel bicycle fleet). 21 Oceanview Terrace, Montauk; marrammontauk.com
Shop
English Country Home: Lighting, mirrors, and vintage and new furnishings; 26 Snake Hollow Rd., Bridgehampton; ecantiques.com
Il Buco Vita: One-of-a-kind glassware, cutlery, jewelry, and art; there’s also a counter for coffee, pastries, and ancient grain focaccia from restaurant Il Buco al Mare next door. 225 Main St., Amagansett, ilbucovita.com
French Presse: A beautiful shop of well-crafted linens for bed, bath, and kitchen/table; 160 Main St., Amagansett; frenchpresse.com
The 1818 Collective: A historic house full of vintage and contemporary furnishings, art, and textiles curated by design industry veterans; 43 Madison St., Sag Harbor, the1818collective.com
Whalebone: A Montauk apparel brand since 2010, celebrating life on the water; 28 S. Etna Ave., Montauk; whaleboneapparel.com
(Left to right) Contemporary art on the 14-acre grounds and meadows of Parrish Art Museum in Water Mill; Vineyard rows near the tasting room at Channing Daughters Winery in Bridge-hampton; In Montauk, a beach of rocks tumbled by waves and interesting sand colors, ranging from beige and amber to deep plum.
Explore
Channing Daughters Winery: Partake in seated tastings with vineyard views at this artisanal winery begun by a sculpture artist; by reservation only. 1927 Scuttlehole Rd., Bridgehampton; channingdaughters.com
Montauk Point Lighthouse: Tour this historic beacon at the easternmost point of Long Island; 2000 Montauk Hwy.; montaukhistoricalsociety.org
Parrish Art Museum: A contemporary art museum and grounds focused extensively on works by artists of Long Island; 279 Montauk Hwy., Water Mill; parrishart.org
Shadmoor State Park: Hiking trails on bluffs overlooking the beach; wooden platforms and stairs to the shore; 900 Montauk Hwy., Montauk; parks.ny.gov/parks/shadmoor/details.aspx
Find even more visitor info:
Visit Montauk, 742 Montauk Hwy., montaukchamber.com
Discover Long Island, discoverlongisland.com
