Sign up for our Newsletter

A Shelter Island view from the ‘Kissing Rock.’ (Credit: Charity Robey)

Shelter Island is more than a charming, boring version of the Hamptons, a bucolic identity that travel writers have stuck on it. The island has welcomed visitors for two centuries with a contrariness that comes with being able to roll up the gangplanks every night and let the rest of the world go to hell. There’s a lot here, especially for people willing to bike or float, and a long summer day is enough time to get a taste. 

Of course, you can drive a car onto the ferry — this is still Long Island. But if you come by bike or rent one from Piccozzi’s Bike Shop (177 North Ferry Road, 631-749-0045), you’ll be pre-adjusted to the pace of the place, summarized by the tag line “Live Slow,” which you may see on a bumper sticker or T-shirt.

Begin your day at Stars Café (17 Grand Avenue, 631-749-5345), located about a quarter-mile from the North Ferry, just up the hill from the bike rental. It’s a great place to have breakfast and plot your route.

Every small town has a place where the mood of the community can be assessed and on Shelter Island, that place is Stars. The regular morning crowd is generally sitting at café tables outside, watching the peaceful and civil coexistence of pedestrians, bicycles and cars at the intersection of Chase and New York avenues and weighing in on island events. New to the menu this year is peanut butter and jelly French toast, a breakfast that can do double-duty as lunch. Owner Pepe Martinez said they are happy to make this delicacy with their gluten-free bread, for those who prefer it.

Before you leave the Heights, a visit to Marie Eiffel Market (184 North Ferry Road, 631-749-0003) is a very good idea, even if you’ve already had breakfast. It’s a great place to buy freshly baked breads and pastries to stock a picnic lunch or eat dockside at the tables in back. Don’t leave without a hunk of her delicious baguette.

The Smith-Taylor cabin on Taylor's Island. (Credit: Monique Singh-Roy)
The Smith-Taylor cabin on Taylor’s Island. (Credit: Monique Singh-Roy)

The island’s most interesting public space is Taylor’s Island, featuring a turn-of the century timber cabin that’s been restored thanks to the efforts of local preservationist P.A.T. Hunt. Technically, it’s not an island, but a tombolo — an acre of rocks and sand connected to land only at low tide — in the middle of Coecles Harbor. Travel by kayak (you can rent from Shelter Island Kayak Tours, 23 North Ferry Road, 631-749-1990) via the Coecles Harbor Marine Water Trail or put in at the Town Landing on Congdon Road. Get more information and a map at

At first glance, Sylvester Manor Educational Farm (21 Manwaring Road) looks like a farm stand with especially great-looking vegetables. But hang out and talk to the folks tending the stand and you’ll quickly discover that this is the business end of a 250-acre educational farm with pigs, chickens, fainting goats and a manor house that was built in 1737 on land that has been farmed since the 17th century. Of course, you can buy some tomatoes, but also consider a walk to see the goats or maybe a tour of the house and grounds.

Then, on to lunch.

The bright yellow walls and tiny lunch counter at Maria’s Kitchen (55 North Ferry Road, 631-749-5450) are cute, but it’s the chalkboard menu neatly listing her signature enchiladas, empanadas, salads and smoothies, which takes up most of a wall, that demonstrates the mission here. Maria is running a serious Mexican eatery and she’s not going to let you leave without tasting something so good that the memory of it will draw you back very soon. Her culinary style reflects her roots in Puebla, Mexico, tempered by a heavy reliance on fresh local produce, a genius for soup-making and a light hand with the hot peppers.

Jim Hull pouring up some of his Forbidden Fruit apple ale. (Credit: Monique Singh-Roy)
Jim Hull pouring up some of his Forbidden Fruit apple ale.
(Credit: Monique Singh-Roy)

Just next door you’ll find Shelter Island Craft Brewery.

If the idea of a microbrewery is to make small batches of local beer with local ingredients, then the Shelter Island Craft Brewery (55 North Ferry Road, 631-749-5977) is the most micro of all. Owner and brew master Jim Hull forages island gardens and beaches for flavors to incorporate into adventurous island brews. Lemon verbena and local honey contribute to the citrusy charms of Liquid Sunshine Wheat Ale, a favorite that’s almost always on hand.

For evening entertainment, the Perlman Music Program, (73 Shore Road, 212-877-5045) is Toby and Itzhak Perlman’s camp for gifted 8-  to 12-year- olds, who play their stringed instruments like accompaniment for flights of angels. The program holds free concerts every Friday and Saturday night throughout the summer on its tree-studded beachside campus, with Itzhak Perlman conducting — and sometimes performing.

SALT. (Credit: Jo Ann Kirkland)
SALT. (Credit: Jo Ann Kirkland)

To cap off your day with a great dinner, consider some of the following options.

The Islander is a great diner built by, run by and frequented by local people. So if you want to see some, go there. Also go if you want a superior burger. 63 North Ferry Road, 631-749-1998.

Vine Street Café offers fine dining with a country feel and inspired use of local ingredients. 41 South Ferry Road, 631-749-3210.

SALT’s lively bar and dining room have lovely views of boatyard and creek and a menu that includes their very popular linguini with local littleneck clams steamed in white wine. 63 S. Menantic Road, Island Boatyard, 631-749-5535.

Red Maple, a stylish restaurant in the newly renovated inn, The Chequit, features New American food. With my right hand on “Mastering the Art of French Cooking,” I swear to you the kale and butternut squash salad with shrimp is fantastic. Tender. The Chequit, 23 Grand Ave., 631-749-0018.

[blankslate_pages id=”d55899831277e8″ type=”card” show_photo=”true” utm_content=””][/blankslate_pages]