Mashomack Preserve is considered one of the northeast’s richest habitats.
Grab your bike, your backpack, and your appetite. We’ve curated the ultimate two-day Shelter Island Staycation for you, departing from the South Ferry, in Sag Harbor, and arriving at the North Ferry, in Greenport. Make the most of summer on the East End with this delicious taste of one of our favorite places.
Your taste of Shelter Island starts at the South Ferry. Hop on the bike and ride one mile to the so-called Jewel of the Peconic, the Mashomack Preserve, which is considered one of the northeast’s richest habitats. Covering over 2,350 acres of land, which includes tidal creeks, woodlands, and freshwater marsh, the Preserve is the ancestral land of the Manhaset peoples. Over 200 species of birds have been recorded at the Preserve over the course of the past 40 years, as well as painted turtles, various butterflies, marine animals, and nocturnal animals. A boardwalk and trail system—trails run in distance from approximately a quarter mile to just over three miles—make Mashomack a great place for visitors of all abilities.
Flanked by Gardiners Bay to one side and Coecles Harbor on the other, this stunning geographical parcel is one of Shelter Island’s most beautiful natural settings. A languorous walk through the trails is the ideal preface to brunch, which awaits just down the road. Catch an unparalleled glimpse of the natural world before embarking on the rest of your staycation.
Ram’s Head Inn sits on over four acres and includes a private beach with boat moorings.
It’s a leisurely four-mile bike ride from Mashomack to the Ram’s Head Inn, where, on Saturdays and Sundays, brunch is served from 11:30 a.m. to 3:00 p.m. The inn sits on over four acres and also includes a private beach with boat moorings, but one of the primary attractions for visitors is its farm-to-table restaurant, where Shelter Island’s seasonal produce and local seafood is always the star of the show.
Start with the sweet corn bisque, which comes alive with smoked bacon, scallion, and chili oil, before diving into one of the restaurant’s signature lobster rolls: Old Bay seasoning, lettuce, and kettle-cooked potato chips. The bloody Mary, amplified with bacon, olives, and lime, is a umami-rich cocktail that adds fuel to the afternoon.
The farmstand at Sylvester Manor Educational Farm is a must-visit stop on any tour of Shelter Island.
Appetite sated, jump back on the bike for a three-mile ride to Sylvester Manor Educational Farm, a former Native American hunting, fishing, and farming ground that has seen 11 generations of European settler families. Originally the site of a slaveholding provisioning plantation, the farm, which was established in 1651, is now run as an organic educational farm where locals can learn about food and the arts.
Beginning in 2009, when Bennett Konesni, a descendent of the Sylvester Family, began growing vegetables on the grounds of the estate, Sylvester Manor has become one of the foremost places to find fresh and local produce on Shelter Island. Guests can visit the farm and the farmstand, which sells vegetables grown on the property, as well as bread, dairy, fruit, wine, yarn, pastries, body products, candles, coffee, and other products grown and made by East End vendors, farmers, and growers.
Léon 1909 is a French- and Italian-inflected restaurant in Shelter Island Heights that opened last summer.
It’s a short ride from Sylvester Manor to Shelter Island Heights, where Léon 1909 opened last summer. (Make a reservation in advance through Resy.) The French- and Italian-inflected restaurant is among Shelter Island’s most popular new additions. Owners Valerie Mnuchin and Robert Mnuchin, a father-and-daughter team (the latter is a former banker who was once the owner of Connecticut’s Auberge property, the Mayflower Inn & Spa) have dedicated their bespoke space to the traditional muted tones of the North Fork: plenty of natural wood, clean lines, and local produce.
Standout dishes are predictably aquatic in nature, and no staycation to Shelter Island would be complete without a nod to the nearby Peconic. Order a plate of the paccheri, made with local chopped clams, roasted tomato, white wine, and thyme; even just a few bites are sure to chase away thoughts of Monday morning. Grilled squid, served with pimenton and oregano, tastes faintly of the ocean, a thoughtful, Provençal preparation that allows the delicacy of the seafood to shine. But even the restaurant’s most simple pleasures—a plate of house-made bread, made from Balsam Farms’ whole wheat and served with cultured butter—are a reminder that what the Island offers in spades is the bounty of Long Island.
A gastronomical dreamscape is only a short ferry ride away.
From Léon it is a short ride to the newly renovated Pridwin Hotel & Cottages, which first opened in 1927 and re-emerged onto Crescent Beach with gusto in 2022. Owned by the Petry family, who has partnered with Cape Resorts to refresh the historic resort, the Pridwin remains one of the island’s iconic hotels, and the redesign has leaned into preserving important details. Each of the hotel’s 33 rooms feature custom beds and side tables, and the resort’s 16 cottages—some of which are even dog-friendly—offer working fireplaces, kitchenettes, and, in some cases, private decks.
After a long day of riding, there may be no better place to enjoy a flawless view of the water, cocktail in hand. Crescent Beach has acquired the moniker “Sunset Beach” for good reason, after all; the beach turns into a ball of pink and orange over the water on each clear evening. At the Crescent Bar, with its retro pink-and-red-striped awning, order a vesper, a classic blend of gin, vodka, and Lillet Blanc (the bar offers classic cocktails in spades).
Crescent Beach has acquired the moniker “Sunset Beach” for good reason
It’s a one-mile ride, when morning arrives, down to the Eccentric Bagel, an all-day takeout spot that has achieved island fame, thanks, in no small part, to its vibrant Generation X décor. New York transplant Darryn Weinstein and his wife Amy opened the spot last year (Shelter Island’s first-ever bagel shop, it must be said), a haunt that is equal parts zeitgeisty sandwich joint and breakfast go-to. The Eccentric Bagel makes over 20 different varieties of bagel, ranging from by-the-book (everything, salt, egg, pumpernickel) to boundary-pushing (smoked bacon, maple cinnamon crunch, Sriracha). Get one with, say, artichoke cheddar schmear, or as part of an elaborate build-your-own breakfast sandwich.
If a stop at the beach is in order (and why wouldn’t it be, after all?), take the two-and-a-half-mile ride down to Wades Beach, a pretty beach that is staffed with both lifeguards and a comfort station. A dip in the water will keep things cool and collected for more afternoon and evening snacking, just as a good staycation intended.
Commander Cody’s Seafood is Jimmy Hayward’s unchanging and unyielding Shelter Island stalwart.
For lunch, take the 7-minute ride to the cash-only Commander Cody’s Seafood, a casual spot that speaks to the traditional ethos of island life. Fried fish comes by the pound here (flounder, hake, sea scallops, cod), and there’s plenty more belly-filling fare to enjoy, too, from the barbecue ribs to the spicy black-eyed pea salad. It’s Jimmy Hayward’s unchanging and unyielding Shelter Island stalwart, a rib-sticking spot that never disappoints.
Peeko Oysters are harvested in Little Peconic Bay.
From Commander Cody’s it’s a three-minute ride to the Peeko Barn, the Shelter Island outpost of Peeko Oysters, which are harvested in Little Peconic Bay. These deep-cupped oysters are farmed by founder and fisherman Peter Stein (the company is based on the North Fork, in New Suffolk). In the barn, guests can create their own small or large tasting experience, looking out into pastoral Shelter Island. Farmer Chris Coyne can arrange private tastings—email him in advance to set up a time and quantity: chris.coyne@steinseafoods.com.
The Chequit sits proudly atop a hill in Shelter Island Heights.
You’ll want to make your reservation in advance for dinner at the Chequit—at Weakfish, specifically, which opened last spring under the smart and studied hand of Greenport chef Noah Schwartz. It’s a 10-minute ride to this stunning property, which sits proudly atop a hill in Shelter Island Heights (the hotel first opened in 1872 as a meeting hall and now features two restaurants and a café, as well as guest rooms and suites).
Weakfish focuses on sushi and seafood, although other Asian dishes make an appearance, too. Grilled tiger prawns come alongside crispy pork belly, edamame, and a broccoli purée, and a house ramen with maitake mushrooms, kimchi, scallions, egg, and pickled bamboo comes with a choice of pork belly, chicken, or tofu. Indulge in the Weakfish Platter, an extravaganza of firecracker shrimp, steam buns, pork dumplings, crab Rangoon, ribs, and scallion pancakes. The restaurant also offers an omakase option for either sushi or sashimi, for $125 per person.
After dinner, head to the Terrace for cocktails or simply commit to the evening by snagging one of the magnificent rooms at the hotel, which was renovated in 2020 after it was acquired by the Soloviev Group. With 19 rooms in the main building that have been refreshed in a minimalist style and 16 rooms in the property’s separate buildings, as well as plenty of space on the porch for sitting and relaxing after dinner, it’s the perfect place to cap a trip that’s just outside the border of home. In the morning, head north, to Greenport, where the ferry, only a five-minute ride away, awaits. Bon voyage.
