A Local’s Guide to Shelter Island

Visit Shelter Island like a harelegger—it’s the only way.

There’s a kooky name for people who were born on Shelter Island, a place with no hospital. These home-birthed citizens are known as hareleggers, because in the days when the movie theater in Greenport had a late show, Islanders left before the credits rolled, and ran like rabbits to make the last ferry of the night.

Today, the ferry service between Greenport and Shelter Island runs later, and when the weather is fine, a day-trip-without-vehicle to the historic and walkable Shelter Island Heights, is fun on foot to balance a carbon footprint.

You must go by boat.

The approach to Shelter Island on the North Ferry is memorable; 15 minutes of sea breeze and bay views with Gardiners Bay and Orient to the East. I step off the ferry, and follow the sidewalk up the hill and under a hedge arch into the heart of “The Heights” a Victorian-era Methodist retreat that began as a community of ornately decorated wooden cottages on curving, intersecting streets with views of the bay around every corner.

Coffee roasted right

Stars at 17 Grand Avenue is a third of a mile from the North Ferry, and a great place for breakfast or lunch. Owner Pepe Martinez got his start as a coffee bean roaster, and the coffee served at Stars shows off his skill, as the morning regulars who occupy the sidewalk tables will tell you between sips.

The Power Burrito- eggs spinach, avocado, Swiss and turkey on a whole-wheat wrap, draws cross country runners and would-be Popeye’s from all over the Island for delicious nutrition. For the rest of us, Peanut Butter and Jelly French Toast, tastes exactly like it sounds, a breakfast that is also lunch.

Baguettes worth walking for

At Marie Eiffel Market, the vibe is casual, international, and the food is seriously good, even thoughtful. From the fragrant and zingy ginger scones, and moist, nutty almond muffins to crunchy baguettes, and the complex flavors of her crusty gluten-free loaf, Marie’s breads and pastries are the foundation of the operation. A recent stint with a Parisian pastry expert has increased Marie’s already extensive repertoire of things baked. A rich seafood stew, and her signature onion soup (topped with the moral equivalent of a grilled cheese sandwich) raise the bar even further.

The Market has three pleasant dining areas; street-side tables in front, long communal tables inside and harbor-side picnic tables in back. A small but well-curated selection of grocery items includes treats such as La Quercia’s celebrated American prosciutto, high quality local and imported cheeses, and a refrigerator case with sandwiches and salads all dressed up and ready to go to the beach with me.

The place to see, and not necessarily be seen, since 1872

The Chequit, one-third of a mile from the North Ferry in the heart of Shelter Island Heights, has been a constant in Island life since it was constructed in 1872 as the dining hall and activity center for the Methodist camp, and later as a hotel, restaurant and bar. At the restaurant, Red Maple, I dine on the patio with views of Dering Harbor or in a booth so private I could conduct covert operations while sampling the extensive selection of excellent Long Island wines by the glass or bottle.

I enjoyed a spunky pink Cosmo at Red Maple’s capacious bar, while a couple of local chefs on their night off and a writer working on his screenplay sampled items from the new menu; small plates of meatballs, a farro risotto, and a trio of flatbreads, including a sweet, smoky creation of sausage and caramelized onion.

Keep on the Sunnyside

A brisk walk along Sunnyside Avenue brings me to Goat Hill, the highest point of land on Shelter Island, and The Flying Goat, a restaurant with great views and a menu that covers all the major food groups: from house-cured salmon and crabcake starters to local weakfish, ribs and veal chops. Greenport Harbor brews are on tap.

Seek the Beach

Beyond Goat Hill is a quarter mile of dirt road, then down the hill to Crescent Beach a lovely, curve of sand and picnic tables. No worries about having a beach sticker when you have no vehicle.

If you miss the last ferry….

Sunset Beach, a boutique hotel, holds down one end of Crescent Beach with 20 rooms, a restaurant, very glamorous clientele, and a snack bar.

The Chequit was renovated and reopened in 2015 with simple, small and elegant guest rooms in the main building and in the adjacent Summer House.

The House on Chase Creek is a homey B&B. Four rooms, each with a private bath, look out over Chase Creek, a birdwatcher’s delight. Breakfast features the owner’s banana bread, and is served on the sun porch with binoculars the better to view the show of fishing, nesting, and migrating water fowl.