Dream Day: Rock-solid Shelter Island fun (2024)

Ram’s Head Inn on Shelter Island. (Photo credit: Doug Young)

Be careful when you float on over to tiny Shelter Island; you might never want to leave. Since it was first dubbed Manhansack Aha Quash A Womack by its original Native American Manhanset residents, this “island sheltered by islands” has drawn people in for its wild, natural beauty, boating and biking lifestyle and leave-your-cares-at-the-ferry-line vibe.

This is by no means an exhaustive list of what’s great about the Rock, but if you’re dipping a toe into a day or overnight visit of isle-awhile fun, here are a few solid suggestions for your island itinerary.

Eat & Drink

At Kyle’s (27 North Ferry Road, 631-749-0579) chef and owner Kyle Seddio’s lovely little restaurant and take-out bakery is open for breakfast and lunch, where she whips up a soufflé-like frittata and house-made jelly donuts that will make you weep, they’re so damn good.

Darryn Weinstein, owner of The Eccentric Bagel (25 West Neck Road, 631-749-5363), brought the very first made-fresh-daily bagels to Shelter Island. Grab one of his excellent classic or creative versions with the schmear of your choice and a cup of good coffee.

Léon 1909 (29 West Neck Road, 631-749-9123) has become a destination for its flame-licked dishes like the dreamy bone-in ribeye, house-made bread and inventive co*cktails, and, of course, the fab fire show from the wall-wide wood-burning oven.

Year-round staple Vine Street Café (41 South Ferry Road, 631-749-3210) serves stellar comforting cuisine that manages to be both fresh and energetic. Excellent service and expectation-meeting fare from owners Lisa and Terry Harwood keeps Vine Street hoppin’ nightly.

Pizza, you say? The island has two solid options sure to please. Owner Frankie Venesina’s Shelter Island Slice (3 North Ferry Road, 631-749-9292) is the place to grab a namesake quick lunch or a full-on meal of wings, garlic knots and pies for the whole fam while you watch a game on the big screen TV or outside at their sweet alfresco tables (pizza pedigree alert: his parents owned the beloved Conca D’Oro in Sag Harbor). For a more trattoria-like vibe, hit up Brad Kitkowski’s Isola (15 Grand Ave., 631-749-9036), where you can eat specialty, wood fired pizzas like the BPT (applewood bacon, hot cherry peppers and sun-dried tomatoes) in the historic 19th-century dining room.

Attached to a garden nursery, White Oak Wine Bar (2 Manwaring Road, 631-749-5814) offers a serene, outdoor sitting area that feels like a secret garden, with cheese plates from parked-on-premises King Reeve Cheese and wines made under the White Oak label by Lenz winemaker Tom Spotteck.

Blues and fish are the order of the day at Commander Cody’s (41 Smith St., 631-749-1851), a no-frills, BYOB, last-of-its-kind fish shack run by owner and fisherman Jimmy Hayward and his daughter, Amanda Hayward. Expect unfussy fresh fish dishes, broiled or fried. Order ahead for Jimmy’s authentic Southern fried chicken and ribs; they’re worth the wait. (Desserts are Amanda’s specialty; don’t pass ‘em up.)

A boaters’ paradise, Salt (63 Menantic Road, 631-749-5535) has a pull-up-your-Boston-Whaler, good-time vibe. Excellent poke bowls, fish tacos and lobster rolls fill you up dockside, and steps-away rockin’ bar The Shipwreck has live music all season long.

Ice cream and summer? Oh, heck yeah! Hit up the Tuck Shop (75 North Menantic Road, 631-749-5939) for all your favorite and then some flavors (they make ice cream cakes too), or the Whale’s Tale (3 Ram Island Road, 631-749-1839) for a round of mini-golf and a cone or cup of your fave sweet treat.

Shop

For one-stop-strollable shopping, the Heights is where it’s at. Both the Shelter Island Pharmacy (19 Grand Ave., 631-749-0445) and Bliss’s Department Store (186 North Ferry Road, 631-749-0041) have the best souvenir T-shirts in town, along with myriad other island-centric items, from coasters and fridge magnets to hats. At Pure Soul (183 North Ferry Road, 516-413-4136) nab gorgeous linen dresses and tops, along with island-vibe purses, earrings and shoes, and Purethread (181 North Ferry Road, Suite C, 631-880-6420) is a bespoke-but-friendly atelier experience. If you want to adorn your home as well as yourself, unique Ram Design Home (181 North Ferry Road, 631-749-5067) will grace your interiors with non-Pottery Barn warmth.

For a more under-the-radar stop, hit up K Studio (16 North Ferry Road), where Karen Springer brings a handcrafted touch of Central and South America to island style, with woven bags, jewelry and a multitude of other pretty surprises.

Play

At over 2,000 acres, Mashomack Preserve (79 South Ferry Road, 631-749-4219) has six different trails of varying distances and wheelchair- and stroller-accessible options through the woods and water-rimming routes of this natural island gem.

Thoughtful exhibits and a robust Saturday farmers market make Shelter Island Historical Society (16 South Ferry Road, 631-749-0025) a fun stop. Bonus: their gift shop offers a multitude of locally made gifts and keepsakes.

Summer is baseball season! Island collegiate team the Bucks represents Shelter Island in America’s favorite pastime against other East End teams. Check the schedule (hamptonsbaseball.org) for home games at Fiske Field.

Perlman Music Program (73 Shore Road, 212-877-5045) offers free concerts as part of their Works in Progress program, where students and alumni perform classical string pieces. Check perlmanmusicprogram.org for this summer’s schedule.

Stay

With 37 rooms divided between the main 1872 building and nearby off-premises abodes, The Chequit (23 Grand Ave., 631-749-0018) in the heart of the Heights offers breakfast-to-dinner dining and a welcoming, friendly downstairs pub that’s popular with both locals and visitors alike.

You can’t beat the sunset views from The Pridwin Hotel & Cottages (81 Shore Road, 631-749-0476). But any time of day, this circa 1927 summery vibe spot always feels like the place to be, with breakfast through dinner dining at the fresh-focused Terrace restaurant and bar, poolside lounging and full-service in-house spa.

With its cedar-shingled exterior, Adirondack chairs facing Coecles Harbor and tucked-away location, The Ram’s Head Inn (108 South Ram Island Drive, 631-749-0811) feels like it’s from a storybook. Old-timey lawn games, unrushed vibes and an excellent on-premises restaurant make this female-owned inn the ultimate escape.

Billed as a bed-and-breakfast, the 44 stylish rooms at Seven (7 Stearns Point Road) are a bit more stylish than your typical biscuits-and-tea haven. Get breakfast delivered to your room in a sweet little wicker picnic basket, play a round of croquet and cool off after in the lovely in-ground pool.

For an idyllic B&B experience, House on Chase Creek (3 Locust Ave., 631-559-2296) offers a sweeping front porch overlooking its namesake body of water. Its also a super convenient jumping off point for restaurants, shopping and renting bikes at Piccozzi’s gas station (177 North Ferry Road, 631-749-0045).

Owned by islander John Sieni, the 200-year-old Candlelite Inn (3 South Ferry Road, 631-834-7578) is one of the island’s more reasonably priced options. Tidy, minimalist rooms with modern and old-fashioned touches are comfy and quiet, and the wrap-around porch is a lovely spot for a glass of iced tea or rosé after a long day exploring.

Amy Zavatto is the Editor-in-Chief for southforker, northforker and Long Island Wine Press. She's a wine, spirits, and food journalist whose work appears in Wine Enthusiast, InsideHook.com, MarthaStewart.com, the New York Post, Liquor.com, SevenFifty Daily, Imbibe, Men’s Journal and many others. She's the author of The Big Book of Bourbon co*cktails, Prosecco Made Me Do It: 60 Seriously Sparkling co*cktails, Forager’s co*cktails: Botanical Mixology with Fresh, Natural Ingredients, and The Architecture of the co*cktail. She is a respected judge for the American Craft Spirits Association’s annual small-production spirits competition, and has moderated numerous panels on the topics of wine, spirits, co*cktails, and regional foodways. She is the former Deputy Editor for the regional celebratory publications, Edible Manhattan and Edible Brooklyn, as well as the former Executive Director of the Long Island Merlot Alliance. She is a member of the New York chapter of the international organization of women leaders in food, wine, and spirits, Les Dames d’Escoffier. The proud daughter of a butcher, Amy is originally from Shelter Island, N.Y., where she developed a deep respect for the East End’s natural beauty and the importance of preserving and celebrating it and its people.