Shelter Island, New York

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Nestled between the two forks of Long Island lies a smaller, not-as-long and certainly not-as-well-known island called Shelter Island. In the 19th Century, it became home to Methodist summer camps, grand resorts and beach cottages and still retains a quiet charm, studded with Victorian gingerbread houses and peaceful beaches. And since it is only accessible by ferry, the community remains surprisingly and wonderfully secluded, especially given its proximity to its more flashy neighbor to the South, The Hamptons.

EAT

Breakfast at Maria’s Kitchen

◐ Shelter Island Pharmacy

Old-fashioned lunch counter with excellent egg sandwiches and hash browns. Best greasy breakfast on the Island. Cash only, though they let you pay at the pharmacy counter with a credit card.

◐ Commander Cody’s

Fantastic seafood and BBQ joint, tucked away in a fish market off Midway Road. The shrimp & grits were transcendental. Cash only. Can close early.

◐ Shelter Island Seafood

Excellent fish market and seafood restaurant. They have a smoker so often you’ll see incredible options like smoked scallops on the menu. Open for lunch and dinner, indoor and outdoor picnic table seating.

◐ Maria’s Kitchen

Incredibly delicious Mexican lunch counter, with gigantic bags of homemade tortilla chips and a killer fish taco. You can also enjoy a full Latin breakfast there — eggs, rice, beans, avocado, maduros — the best. Limited seating inside, though they do have a lovely garden seating area outside. Or, take it to-go!

The Islander

Wonderful diner, open for breakfast and lunch. Everything you could want + local beers & wine.

Stars Cafe

Always busy breakfast & lunch spot. The breakfast burritos are the best option here. The coffee isn’t great and the service can take forevvvvver.

Salt

Waterfront restaurant adjacent to the Island Boat Yard with a lively atmosphere. Good for a big group.

◐ Isola

A recent addition to the island, delicious Italian comfort food — think pizza and pasta. It can be a little pricey, but the portions are shareable and they offer a Mon–Thurs night dinner special (chicken parm, meatballs, etc.) and one of the few bars that’s open past 8pm.

◐ Vine Street Cafe

Best fancy dinner out on the Island — though you will pay for it. Seasonal, local dishes including excellent seafood. Be sure to make a reservation if you’re dining in the summer season. If you don’t want to shell out for a meal here, visit their market around the back for to-go meals, jarred sauces and snacks, or go to their lunchtime food truck that’s parked out front during the summer. Or, grab a drink at the bar with some of the best spiced nuts you will ever taste. Beloved by Martha Stewart AND Ina Garten.

18 Bay

Seasonal 4-course Italian-inspired prix fixe, changes weekly. Great for a special occasion.

Marie Eiffel’s Market

Insanely expensive salads, sandwiches and baked goods. That said, it’s the only place to get a decent cup of coffee and a pain au chocolat. If the weather’s nice, take your food out the back to the dockside seating area overlooking the water and the Shelter Island Yacht Club.

Farm Stands

Peeko Oysters — Fresh oysters $1/each out of a garage on 114, next to Black Cat Books. You’ll see the sign!

Sylvester Manor Farm Stand — 21 Manwaring Road. You can tour the farm (and windmill!) as well. Check the website for opening times.

Havens Farmers Market — 16 S Ferry Road. Open Saturdays, June–October. Check out the pickle guy!

Island Time Farmstand — Tiny stand on 114, just past White Oak, selling wildflowers and veg in season, including excellent tomatoes. Drop your cash in the box.

King Andrew Cheese — In the parking lot of Shelter Island Seafood, a covered wagon offering the best cheese on the Island.

DRINK

Shelter Island is more of a “drink rosé on your porch” place than a bar place, but here are a few suggestions!

The Shipwreck Bar

Salt’s dockside bar, built within a 39-foot schooner. Enjoy a Dark & Stormy and some corn-hole overlooking Menantic Creek and West Neck Harbor.

Shelter Island Wine & Spirits

Wonderful wine and liquor store in the Heights, across from Marie Eiffel. They have tons of wine at all different price points.

The Dory

Shelter Island’s one and only dive bar. Yes, it looks amazing, hanging over a creek and covered in nautical bric-a-brac. No, they don’t want you there. Have fun!

Sunset Beach

If you must, go for lunch. It is truly awful, though. Overpriced, over-hyped and full of jerks and Real Housewives. Tip: The beach is a public beach — bring your own wine and snacks and enjoy the sunset slightly further down the coast. Open only in summer.

SHOP

◐ Black Cat Books

Wonderful used bookstore. Right across the street from Maria’s.

Marika’s

A mountain of antiques scattered across a lawn and within several lean-to’s. Many treasures to be found!

PLAY

Mashomack Preserve

◐ Mashomack Nature Preserve

One third of the Island was acquired by The Nature Conservancy in 1980 in an effort to stop development and protect osprey nesting areas. You can explore it through a series of looped hiking trails, ranging in length from 1–10 miles. (No bikes or pets.)

Shelter Island Historical Society/Havens House Museum

Tour the house Monday–Saturday, 10am–2pm. In Summer, visit the green market to stock up on local bread, cheese, fish and produce. Saturdays, 9am–12:30pm. Go early to get the best vegetable selection.

The Beach

They do exist here! But you’ll need a town permit to park near most of them, or risk a very expensive parking ticket. Pick up a permit at the Town Clerk’s Office at the Town Hall. Wades Beach is lovely, it overlooks Shelter Island Sound and has the added bonus of bathrooms. Crescent Beach is more sheltered, with a great sunset view, but it does get crowded due to the Sunset Beach scene.

Piccozzi’s Garage & Bike Shop

Bike rental is $25 for a full day. Less for a half day.

Shelter Island Kayak Tours

Rent single and double kayaks or paddle-boards to explore the Coecles Harbor Marine Water Trail.