Shelter Island, nestled between the North Fork and the South Fork of Long Island and a mere 90 miles east of Manhattan. Take an eight minute ferry ride from Greenport and see what makes this the perfect destination for a weekend getaway. It’s unspoiled beaches, charming town, rambling gardens and beautiful historic homes make you feel as though you’ve just stepped into a Norman Rockwell painting.
WHERE TO STAY
The Chequit – Located at the top of the hill, in easy walking distance of the North Ferry, this 37 room refuge was built in 1872 as a dining hall and gathering place for Methodists on a religious retreat. The hotel has a nice laid-back vibe. The rooms are bright, clean and carefully appointed with colorful Turkish rugs and a soothing palette of pale blues, pinks and whites. Breakfast (included in the room rate) is an informal spread of fruit, yogurt, pastries and warm sweet and savory dishes. Spend the afternoon curled up on the veranda with a glass of wine and a view of the harbor.
The Pridwin – A classic full scale resort on Crescent Beach offering a tennis court, private beach, pool, kyacks, paddle boards and bikes for local touring.
Shelter Island House – One of the first hotels on Shelter Island; Shelter Island House is set on a quiet street just a block off the infamous Sunset Beach. Historic charm is the best way to describe this hotel, complete with white-washed walls, a wrap-around porch and rooms decorated in soothing pastels. Spend your days lounging by the pool, curling up on the porch to read a book or by grabbing one of the hotels bikes to head to the beach.
WHERE TO PLAY
Head to the beach. Shelter Island is surrounded by beaches and there is no shortage of sand, seashells and swimming. There are two public town beaches, Wades Beach and Crescent Beach, both of which have lifeguards and bathroom facilities. I found these too crowded and sought out the more quiet/private beaches such as Shell and Silver Beach.
Explore the unique and natural beauty of the island by kyack with one of Shelter Island Kyack Tours. Glide along at a gentle pace and take in the views of local Osprey, Terns, fish and other marine life in the clear waterway. Get lost in the beauty of the landscape untouched by man.
Spend a Saturday morning at the farmers market held at the Shelter Island Historical Society on Route 114. Flowers, local produce, fish, breads, pies, cheese, local honey and more. Mingle with the locals and learn about the agricultural history of the island.
Take a hike through Mashomack Preserve. The 2,000 acres of preserves and trails cater to all skill levels. Edged by 12 miles of sandy coastline, the preserve is an area of magnificent scenic beauty. The combination of tidal creeks, woodlands, fields and coastline make it the perfect spot for a morning hike.
Rent a bike from Piccozzi’s Bike Shop (631-749-0045) and tour the island. The roads are almost all shady, the hills moderate and the traffic is light. Pack a picnic and head to the beach or ride to my favorite area, Shelter Island Heights and check out all the architecturally diverse homes ( this area is listed on both the United States and New York State Register of Historic Homes).
EATS ON THE ISLAND
Marie Eiffel Market – Alongside the harbor on North Ferry Road this is the place to go for your morning coffee and freshly baked pastries. Marie Eiffel sells everything from salads to pizza, specialty grocery items to artisan French and Italian cheeses. It’s the perfect place to head if your planning a beach picnic.
Salt – Perfect spot on a beautiful day. Dine on fish tacos, lobster rolls and a full sushi menu as you watch the boats coming in and out of the marina.
Red Maple – A collection of mismatched tables and chairs arrayed under a big maple tree on The Chequit hotels front lawn serving a seasonally inspired American menu.
18 Bay – Situated in a house that dates back to 1873 the spirit of this restaurant is country casual. A pre-set four course Chef’s menu that changes every week is a direct reflection of the local market.
Vine Street Cafe – Local farmers, fishermen and winemakers supply this Long Island staple, where East Enders feast on delicious pastas and their famous miso glazed salmon.
Don’t leave the island without trying one of the amazing black and white milkshakes from Shelter Island Pharmacy. No it’s not a restaurant. Yes, it is the local pharmacy, but their shakes and floats are to die for!
GETTING THERE
From Greenport take the Shelter Island ferry. From Sag Harbor on the South Fork, follow signs to Shelter Island ferry in North Haven. Both run several times an hour, roughly from 6 am to midnight.