Offseason Shelter Island: Serene getaway with destination dining

Poised between the tines of the North and South Forks, Shelter Island is almost as far as you can go and still be within the 631 area code. In the winter, it feels even more remote as summer residents decamp, leaving full-timers the run of its wind-swept solitude. And if wind-swept solitude is your thing, you can’t do better. Not that you can’t be well looked after: One proper hotel (The Ram’s Head Inn) and one B&B (House on Chase Creek) plan to stay open, along with dozens of Airbnbs — the upside is that rates are a fraction of what they are during the high season. Mashomack and other nature preserves offer miles of hiking trails, and, with fewer cars than usual, the roads are perfect for cold-weather cycling.

DESTINATION DINING

Even in the summer, Shelter Island’s restaurant scene is modest compared to those in Greenport and Sag Harbor, the two closest mainland villages. Winter means hibernation for many popular venues, among them Sunset Beach, Marie Eiffel Market, Opties and Dinghies, the newly restored Pridwin Hotel and The Chequit inn. But the island’s two best restaurants, Vine Street Café and Léon 1909 plan to stay open, albeit with limited hours.

Seven days a week, 12 months a year, though, you can count on The Islander. That’s where you’ll find full-time residents Alix Shearer and Kiki Boucher enjoying omelets and salads most Thursdays at lunchtime after teaching their French conversation class at the library. Set back from the road in a little clearing in the woods, it’s the closest thing Shelter Island has to a diner.

Both women said they preferred the island’s quiet winters to its frantic summers but allowed that the cold-weather dining options are limited. "We understand that it’s a tough economic model," Shearer said, "but we really appreciate the places that stay open during the winter." Their student Sandra Saiegh (who travels from East Marion to get her Français on) noted that chef-owned places tend to be more dependable. Otherwise, she explained, "It’s a game of musical chairs after every season: Are they going to stay open after Labor Day? Who’s the new chef?"

That’s not an issue at The Islander. Manuel Lopez has been manning the grill here for more than two decades. He came aboard when the place was called Pat and Steve’s, owned by founders Pat and Steve Lenox, and stayed through its transition to new owners and a new name. Since 2024, he and his business partner, Hugo Montoya, have been running it.

Lopez is still at the grill, supervising breakfast favorites such as the West Coast Benedict (with avocado and tomato filling in for Canadian bacon) as well as burgers, sandwiches and wraps for lunch, and, after 5 p.m., pot roast or meatloaf, cod or shrimp tacos, crab cakes, fish and chips, cheese tortellini and more. If you’ve got children in tow, bring them here. Not only is there a kids’ menu but also coloring books, Uno and Jenga.

He didn’t want to fiddle with the menu too much, but Lopez has managed to honor his native Guatemala with a take-out only menu he calls La Pequeña Isla. Look for tacos made with homemade tortillas, nachos, wings and two tributes to Guatemala’s hot dog culture: the mixta (hot dog in tortilla) and the shuco (on a bun).

Boucher quipped that The Islander is "the only place to eat lunch inside during the winter," but, reminded of Commander Cody’s, less than a mile away, was quick to add, "I always forget about it — it’s so out of the way!" This caused the group to crack up since "out of the way" describes every venue they frequent — and the island on which they live.

Cut her some slack, though, since Commander Cody’s is the rare Shelter Island eatery that is tucked into a residential street off the main drag, Route 114 (a.k.a. Ferry Road). And it’s rare for many other reasons: Founded by Jim Hayward in 1993 (and named for his dog, Cody), the agreeably ramshackle establishment serves as a counter-serve restaurant, fry shop, fish store, barbecue pit and caterer.

Hayward, 90, came to Long Island to fish in the ’50s, but he carried with him the culinary traditions of his native South Carolina. Nowhere is this more evident than in his supernal fried chicken. While Hayward keeps an eagle eye on the operation, it’s now run by Aiden Poleshuk, who grew up on Shelter Island and said, "I feel like I have worked in every restaurant here."

Poleshuk revealed that the chicken gets seasoned overnight with paprika, cayenne, oregano, black pepper, salt and sugar (amid other, undisclosed, ingredients) before being dredged in unseasoned flour and fried outside in two ancient skillets. That the chicken is not completely submerged in the oil — as it would be in a deep fryer — is critical, he said. Each bird is cut into 10 pieces and while there is more demand for dark meat, "There’s nothing we can do. We only buy whole chickens and cut them up here." Whether you dine in or take out, your crisp, juicy russet morsels will be tucked neatly into a carton, thoughtfully topped with a length of paper towel and accompanied by a cup of Frank’s RedHot sauce.

A few paces away from the skillet station is a smokehouse for ribs and pulled pork. In the kitchen itself, the deep fryer gets plenty of business handling the fresh fish that Cody’s also sells retail. Shrimp are butterflied for maximum surface area and there are local oysters, flounder and scallops, plus crab cakes and broiled salmon.

Poleshuk treasures the offseason, when Cody’s can provide an "affordable option to locals and, especially, local tradesmen." He has a philosophical approach to the feast-or-famine business cycle. "During the busy season, the positive is that rush you get when you’re working and there’s no time to think." The negative? "The same things."

OFFSEASON APPEAL

When the locals want to celebrate big, they head for Vine Street Café. Married chefs Lisa Murphy-Harwood (sweet) and Terry Harwood (savory) moved here in 1999, opened this casually elegant restaurant in 2003 and have been refining and expanding ever since. The original dining room now comprises three distinct dining areas and a hopping bar. With lots of weathered wood, vintage tiles and plastered walls, it’s polished and cozy in equal measure.

In 2009, the building’s foundation needed shoring up and the Harwoods took the opportunity to install a market around back. That’s where you’ll find a selection of homemade pasta sauces (made from the Harwoods’ own tomatoes) along with their own hot and barbecue sauces, chutney and artisanal breads plus a well-curated assortment of farmstead cheeses, cultured butter, tinned fish, snacks and treats. (File this away if you plan to rent a house here.)

Murphy-Harwood describes their cooking style as American bistro. "We are classically trained but not afraid to update the classics. We’re always going for something clean and unfussy."

"Classic" means they make Bordelaise and au poivre sauces for the steaks that come with hand-cut fries; they pan-roast lobster bodies to make the stock for their lobster bouillabaisse. "Updated" describes the fried calamari that’s served with frisée and pea shoots; the duck confit that stars in a bowl with jasmine rice, spicy broccoli rabe and a seasonal chutney; the zoodles you can have with your classic Bolognese ragù.

Even in winter, Friday and Saturday nights often bring a Hamptons crowd, said Murphy-Harwood. "It’s mostly locals on Sunday, Monday and Thursday." They have good reason to come for the plats du jour: Sunday is a three-course prix-fixe menu for $44; Monday is that VSC lobster bouillabaisse ($56) and Thursday is a popular rigatoni alla vodka with chicken and the same sauce available for purchase at the market.

Staying open year-round is a foundational principle for the owners of Vine Street. "Do we make money in the offseason? No," said Murphy-Harwood. "But we need to be open to give our people the hours year-round. If we closed every fall, it would be ‘thanks for working 300 hours a week, see you next year.’ And if you keep starting and stopping, you’re not growing and learning."

If there’s one spot on the island that caters to every segment of society, it’s Maria’s Kitchen. Opened 14 years ago by Maria Serano, it’s a mashup of full-service deli, authentic taqueria, Mexican grocery and wellness boutique. Where else could you find packets of keto collagen flakes, sun-dried goji berries and reishi mushroom powder sharing the shelf with Mexican candy, Peruvian pepper paste and a "mofongo party mix" consisting of chicharrón, plantain, yuca?

WHILE YOU'RE THERE

If you’re dragging (or need a burst of energy before entering Black Cat Books, across the road, or Marika’s Eclectic Boutique or the Shelter Island History Museum, less than five minutes away), Maria’s supplies 20 freshly pressed juice concoctions and 14 smoothies. But the main event is a selection of the best tacos on Long Island, anchored by homemade tortillas and filled with everything from chicken or pork to goat, oreja (pig’s ear) and alambre, a savory mix of shaved beef, chorizo, onions and peppers. Maria’s brother, manager Narciso Serrano, said a favorite order among his Mexican customers was the Taco Placero, fully loaded with meat, tortillas, rice, potatoes, grilled onion, jalapeños, avocado and a hard-boiled egg. There are also burritos, quesadillas, chimichangas, tortas, grill platters, wraps, burgers and more.

Maria’s has a few tables outside but, in cold weather, it’s takeout only. Unless, that is, you can snag a table at neighboring Shelter Island Craft Brewery, which, said owner Steve Pisacano, he is hoping to keep open most winter weekends. If he does, it’s a great place to quaff away the afternoon, sampling the wares — there are always an IPA and pilsner on tap, plus seasonal offerings. And you might chase your tacos with some local oysters. How local? Peeko oysters, farmed in the Peconic Bay, operates an "oyster barn" right across the street. (If you know how to shuck, consider picking up a bag for later use.)

As you head north on 114 from Maria’s you’ll pass the Shelter Island IGA and, if you ever decide to rent a house instead of a room, it’s going to be your best friend. It may look a little shabby but it stocks treasures from all over the world: grass-fed beef from New Zealand; Ramune soft drinks from Japan; seafood from Braun in Cutchogue; D’Artagnan chickens, Ronnybrook milk and Bread Alone sourdough from the Hudson Valley; Bianca Napoli tomatoes from California; frozen Indian entrées and pizzas from Table 87 in Brooklyn; and Indian ghee, Greek olive oil and pretty-darn good-looking produce.

Across the street from the IGA is White Oak Farm and Gardens, a leading landscape design and garden center. The retail shop is closed for the winter, but the property also houses a charming country store operated by Stars Café, whose "mother ship" is three minutes up the road in the Shelter Island Heights Historic District.

Lydia Martinez Majdišová and Pepe Martinez took over Stars in 2005. Open every day except Christmas, it’s the community hangout and coffee epicenter. Specially roasted for Stars by Tend in Shirley, it comes pulled and dripped. There are extensive breakfast and lunch menus and house-baked cookies, coffee cake and muffins (one standout: the not-too-sweet corn).

"The Heights" functions as the island’s downtown. Along with Stars Café, you’ll find the Italian restaurant Isola, Bliss’ Department Store (handy if you need a sweatshirt or sunglasses or a Scrabble board or a strainer), Shelter Island Hardware and a number of boutiques that will probably be closed.

Looming over everything is The Chequit, which got its start in 1872 as part of The Shelter Island Grove and Camp Meeting Association of the Methodist Episcopal Church, a religious camp that evolved into a summer community. It became an inn in 1909 and, after a few changes of ownership, was purchased in 2020 for more than $3 million by the North Fork’s mega-landowner, Stefan Soloviev. His ex-wife, Stacey Soloviev, restored and reopened it the following year, along with its restaurant, cafe and tavern. All those ventures closed last fall, amid hopes they would reopen in the spring. She also bought the century-old Shelter Island Pharmacy around the corner. The shop, with its vintage lunch counter, remains open (for now) even as it ceased filling prescriptions in October.

A RECENT NEWCOMER

Another recent local investment seems to be paying off more handsomely. Léon 1909 opened in 2022 and quickly became one of the hottest spots on the East End. All traces of the building’s former tenant, Capital One bank, were expunged in favor of a dream of a modern farmhouse: The rustic-chic dining room is crowned by a vaulted, timbered ceiling that almost rivals the restaurant’s dominant feature, an enormous hearth used to roast and grill most of the meats and vegetables.

Owners Valerie Mnuchin and her late father, Robert, have been well-served by general manager Chris Clark, his wife, beverage manager Gillian Georges, and executive chef Armond Joseph, whose fealty to local produce means the menu changes frequently.

Most of the year, however, you can start your meal with a crudo of Montauk "royal red" shrimp, and there is always a small flock of roast chickens hanging near the hearth. Make sure you order one — it’s impossibly smoky and juicy, accompanied by seasonal vegetables and a bracing salsa verde. Also from the hearth: ember-roasted fennel, dry-aged steaks, a fire-roasted burger, a local fish.

Working with live fire, Joseph said, makes Leon’s "the hardest kitchen I’ve ever worked in." With no knobs or dials, cooking times are determined by how close to the coals the food is. (He tries to use white oak — exclusively from Shelter Island — which burns clean and "builds coals quickly.")

He appreciates that Hamptonites keep the place busy seven days a week from Memorial Day through Columbus Day but believes that Léon really comes into its own during the offseason. "A snowy night on Shelter Island, you walk in here and see this fire? It may be a summer place, but it’s built like a winter restaurant."