23 Grand Avenue, Shelter Island, NY 11965
631-749-0018
Lunch and dinner seven days in season. Sunday Brunch.

David Bowd and Kevin O'Shea, the Provincetown hoteliers who bought the rambling inn in Shelter Island Heights in 2014, did a top to bottom remake and reopened it in 2015. The restaurant is called Red Maple and offers "shareable" plates with a menu that boasts Montauk fluke, local produce and a raw bar. There's a selection of light bites, imaginative cocktails, and wine on tap. Coffee at the White Hill Cafe is by Jack's Stir Brew and the pastries are from Baked. Breakfast in bed is a nice idea. 

Smith Street and Midway Road, Shelter Island, NY 11964
631-749-1851
Seven days 11 a.m.-10 p.m.

Commander Cody's, a year-round fish market with dinners to go and outdoor tables in summer, is off the beaten track. Expect fish that is local and in season, along with fried chicken and ribs. It's not afraid to serve fresh bluefish but it sells smoked fish, too. 

185 Bridge Street, Shelter Island, NY 11965
631-749-4300
11:30 a.m.-10 p.m. weekdays, until 11 p.m. weekends.

The Dory is on the edge of Chase Creek at Dering Harbor, with ducks and swans almost within touching range. It's a great place to escape the summer rush and have simple food at reasonable prices. There is an indoor dining room and bar, but eating on the big deck over the water is the way to go. There are always specials and the menu includes the familiar - calamari, Greenport oysters, burgers, grilled Cowboy steak, mussels, and lots of fresh fish. Jazz on select days.

23 North Ferry Road, Shelter Island, NY 11964
631-749-0053
Open for dinner, Wednesday-Monday, 5 p.m. Crudo Bar 3 p.m. Reservations needed for 7 or more.

You know it's haute cuisine when recipes include such exotic ingredients as stinging nettles. Elizabeth Ronzetti and Adam Kopels, the chefs and owners, who have considerable culinary training - he worked with Mario Battali, for example - moved their Bayville restaurant to what had been Planet Bliss on Shelter Island in 2011 and have been getting accolades ever since. The menu is small and changes weekly, in keeping with what is available locally. A la carte ordering is possible only in the bar but guests go for the chef's prix fixe dinner, at $68. It has four antipasti which might include house-made chicken and ramps sausage, followed by a pasta, which also is made in-house, and a choice of entree, which might be Hudson Valley duck breast or fluke or sea bass. One night dessert was strawberry-rhubard crostada with buttermilk ice cream. Vegetarian, vegan and pasta tasting menus are available.

26 Sunnyside Drive, Shelter Island
631-749-5424
Wednesday-Sunday, Lunch and dinner noon-9 p.m. Call for summer hours.

With scenic views overlooking Dering Harbor and Peconic Bay, local chef Peter Ambrose has opened the Endless Summer Grille at the Shelter Island Country Club.  Serving two forks clam chowder and veggie summer rolls, fish and steak tacos, tuna-endless summer style, burgers and ribs, strip steaks too. The links are open to the public as well. 

63 North Ferry Road, Shelter Island, NY 11964
631-749-1998
Friday-Sunday 6 a.m-8:30 p.m., Tuesday-Thursday 6 a.m.-3 p.m., dinner later in the season.

The Islander serves a coffee-shop menu for breakfast, lunch, and dinner. Monday night has burgers said to be too big to finish. Otherwise there are pancakes, sandwiches, steaks, fish, and salads. Drop in to see the mural by Shelter Island's own Catherine Brigham.

27 North Ferry Road, Shelter Island, NY 11964
631-749-0579
Seasonal. Dinner, Thursday-Sunday from 5 p.m. Breakfast and lunch, Saturday and Sunday, 8 a.m.-2 p.m.

Kyle, who uses only one name, gained knowledge of various cuisines in her travels and that is reflected in her restaurant's menus. Falafels and Buddha bowls are signatures as are hand stretched pizzas and  house-made baked items. They are launching a Dr. Smoothie organic juice bar this year. 
 

184 North Ferry Road, Shelter Island Heights, 11965
631-749-0003
Seven days, 7 a.m.-7 p.m.

When you enter the market the first thing you see is food-and lots of it! It is an authentic French bakery/gourmet market with North Fork produce, an organic and raw juice bar, a brick oven for handmade pizzas, and a great variety of sandwiches and hot meals. Eat on the outdoor deck with a water view, or take it to go. 

81 Shore Road (Crescent Beach), Shelter Island, NY 11965
631-749-0476
Seasonal. Late June to Labor Day. Breakfast 8-10:30 a.m., lunch 12:30-3:30 p.m., dinner 6-10 p.m., 10:30 p.m. on weekends. Bar menu served all day. Indoor and outdoor seating. Reservations encouraged.

The 85-year-old Pridwin Beach Hotel , at the end of Crescent Beach, offers fine sunset views and is a mainstay on Shelter Island. The Petry family, father and son, go fishing and provide the restaurant with their catches, and they take advantage of what grows on the North Fork's farms. There's an extensive list of Long Island wines. The Wednesday night cookout with live entertainment is very popular. The Pridwin Lounge is great for drinks, including cocktails with infused liquors and syrups. Boaters are welcome.

108 Ram Island Drive, Shelter Island, NY 11965
631-749-0811
Seasonal. Dinner, Wednesday-Monday 5-9 p.m., Saturday lunch 11:30 a.m.-3p.m., Sunday brunch, 11:30 a.m.-3 p.m. Closed Tuesday.

This romantic, somewhat formal inn has lawns and gardens spreading down a hill toward the water, trees with swings, and a long veranda where you can enjoy a drink in the summer. In winter, there are fires on the hearth to keep away the chill. Brunch, which offers everything from crab cakes to omelettes to rich desserts, is popular. The menu changes with the seasons. Reservations very much encouraged. Sunday night jazz in summer.

55 North Ferry Road, Shelter Island
631-749-5977
Open 7 days, noon-dark in season.

Jim Hull, a charter boat captain for 26 years in  Shelter Island and Montauk,  opened the brewery in July 2015. There are always 8 handcrafted small batch beers on tap, made with Shelter Island ingredients, like honey, hops and salt to name a few. There is a pairing menu with flatbread pizzas, crostini, patatas fritas, arancini, lobster rolls, pretzels and hot dogs. 

17 Grand Avenue, Shelter Island Heights, NY 11965
631-749-5345
Breakfast and lunch, seven days, 6 a.m.-4 p.m., 6 a.m.–6 p.m. in season

Year round, and in the heart of Shelter Island Heights, Stars Cafe is a small, friendly, casual cafe with indoor and outdoor seating. Smoothies, a juice bar, and in-house roasted organic coffee are featured. Its local husband-and-wife owners are committed to homemade ingredients, whether in American or Latin dishes. Smoothies, organic juices, and the cafe's own roasted coffee are featured, along with desserts and warm pastries baked daily on the premises. In the warm months, the building's lower level becomes an ice cream shop.

35 Shore Road, Shelter Island, NY 11965
631-729-2001
Monday-Thursday, breakfast 8 a.m.-noon, lunch noon-3 p.m., dinner 6-10:30 p.m., Friday-Saturday, breakfast 8 a.m-noon, lunch noon-4 p.m., dinner 5:30-11:30 p.m., Sunday, breakfast 8 a.m.-noon, lunch noon-4 p.m., dinner 5:30-10:30 p.m. Modified menu available between lunch and dinner.

The restaurant, part of one of the hotels owned by Andre Balasz, is on the very edge of Crescent Beach on Shelter Island with an unimpeded water view. It is built on three stepped rooftops and looks as if it has been scooped up by a tornado. The first rooftop is a bar, which is always open late, usually to 4 a.m. on weekends. The next step is a dining room with a roof but no sides, and the last step, literally in the treetops, is a deck topped only by strings of lanterns. The menu tends toward the South of France, with bouillabaisse, grilled lobster, filet mignon au poive, and moules frites. The place is fairly expensive: steak frites is $44, and a plate of crudités is $28.

15 Grand Avenue, Shelter Island Heights, NY 11965
631-749-4114
Dinner seven days during summer, call for hours. Reservations suggested, especially for six or more.

This pretty restaurant is in a classic gingerbread house. Family owned and operated, it has pastas, seafood, chicken, and veal. Regulars recommend the cioppino and say you should share it if you aren't a big eater. The bar out back attracts a late night crowd. Live music on Fridays.