Last Updated on September 15, 2021 by Malerie Yolen-Cohen and Sandra Foyt
WHY GO: Where is Shelter Island NY? Picture the two prongs of land at the Eastern end of Long Island NY as the letter V. The Peconic Bay separates the North Fork (wineries) from the South Fork (Hamptons). Shelter Island is lodged in the Bay, right between the forks.
How do you get to Shelter Island? It’s accessible only via 10-minute car ferries from either Sag Harbor or Greenport, NY. Shelter Island is, in effect, a getaway from a getaway. To/From Greenport NY (North Ferry) or Sag Harbor NY (South Ferry). It’s the only way to get on/off the island. $12 each way with car from Greenport ($18 same day round trip). $15 each way from Sag Harbor ($20 same day round trip).
The island doesn’t have any shouty ad campaigns. There are no nattily dressed 40-somethings clinking wine glasses on a Shelter Island beach in glossy magazine photos.
If you’re hoping to bump into a celebrity, look elsewhere. Shelter Island is a spotlight-free zone, except for the discreet Itzhak Perlman Music Program, which brings young music prodigies here in the summer months.
But, if you aim to get away from it all, walk in the woods, bike beautiful tree-canopied winding roads, collect shells, and decompress, stay here. Especially during off season in September and October when the crowds have left. There’s a wonderful nature preserve, several good restaurants, and a smattering of hotels and inns – mostly sedate (but one drawing a Hampton’s – style crowd). Where to go/what to do on this little island? Read on.
What to Do on Shelter Island (with stop in Sag Harbor NY)
VISIT/WALK: Mashomack Preserve
Taking up a nearly a third of Shelter Island, this 2,029-acre Nature Conservancy wildlife refuge is one of the best run and locally treasured preserves in the region. Though busiest in the summer season, there are programs here throughout the year.
Start in an interactive Visitor’s Center, with humble “please touch” exhibits that highlight forest, meadow, freshwater wetlands, salt marsh and shoreline habitats. You can’t miss the somewhat macabre heads of two deer who died locked in horns.
There are five well-marked trails of various lengths. With 12 miles of shoreline, 45 small ponds and 7 salt marshes, there’s plenty to do and see here. Better yet, each trail has its own unique aspects.
If you only have a few minutes, stroll the wheelchair accessible 1/8th mile forest boardwalk, which paints visitors in dappled sunlight through a canopy of trees. The gazebo at the end of the 1 ½ mile mostly wooded Red Trail is a favorite place to pop the question. Apparently, many couples have gotten engaged there.
Love Bluebirds? Hike the 3-mile open-meadow Yellow Trail to see lots of them. The 6-mile Green trail is the most diverse and most popular, with woods, meadows, and three salt marshes, that leads to a bluff with water views. Lastly, you can spend hours on the 10-mile Blue Trail with views of Gardiner’s Bay.
BIKE: All Over Shelter Island
In season, it will be impossible to find parking anywhere near beaches. So, of course, bikes come in handy. Off season, in late Sept/early Oct., winding roads are almost empty, and the views lovely. Go ahead, explore. Most of the island is residential.
You’ll be in shell nirvana at this 8-acre preserve at the very end of Big Ram Island. Though you’d have to grow an exoskeleton to be comfy sprawling out to catch some rays, the crunchy, sharp-edged beach is the perfect place to find a high concentration of “Mermaid’s Toes,” clams, cockles, scallops, and other beautiful shells.
VISIT: Sylvester Manor
Sylvester Manor was established in 1652 as a provisioning plantation for the Barbadian sugar trade. It’s been in the same family since then. The 243-acre former plantation core encompasses farm fields, wet and wood lands, formal gardens and grass lawns, numerous barns and buildings, and the Manor house.
Though the 1700’s home is not open to the public on a daily basis, you are welcome to wander the beautiful grounds and pick up organic meats and produce at the Farmstand.
Eleventh generation estate owner, Bennett Konesni, the founder of Sylvester Manor Educational Farms, envisions bringing the culture back to agriculture. His mission is to preserve, cultivate and share historic Sylvester Manor to ensure that food and art remain connected to community and the land, Check website for schedule of events.
LISTEN: Perlman Music Program
In summer, catch a free “works in progress” concert presented by genius musicians ages 12-18. Check website for events.
WALK: Sag Harbor Self-Guided Walking Tour
The town of Sag Harbor is on the “Hamptons” fork (South) of Long Island. And, like the Hamptons, it has a tinge more swank than Shelter Island. A Customs Port post-US Revolutionary War (one of two in New York – the other in Manhattan) with a railroad station, it was a rough and tumble, ethnically varied, busy end-of-land town.
Whaling brought a diverse workforce, and thus a diverse citizenry, to Sag Harbor. When whaling declined in the mid 1800’s, light industry – most notably the Bulova Watchcase Factory – moved in. (Bulova closed in 1980).
Pick up a 3.5 mile walking tour map at the Sag Harbor Whaling Museum or in the very easy to identify windmill at the Wharf. Plan to spend a few hours strolling by all 43 historic sites, and of course stopping into a boutique or two.
On the Peconic Bay side of the South Fork, Sag Harbor was safe haven for whaling ships coming in from the often-dangerous Atlantic Ocean. The building itself, designed in 1845 by a starchitect of the day, Minard Lafever, is a stunning classic Greek Temple-front mansion.
Galleries on one floor showcase scrimshaw, portraits of whaling captains, harpoons and whaling curiosities galore. My favorites – decorated women’s corset whalebone stays. Open May1-Oct 31 daily 10-5, $6 adults, $2 kids.
Restaurants on Shelter Island
EAT: Ram’s Head Inn
Food is fine, service is great and ambience stunning. In warm season, ask to sit on the patio perched over a lawn that slopes down to a gazebo, tennis courts, a small beach and bay beyond. Drink in the sunset with your wine and feel one with nature.
EAT: Locals Also Love
SALT (if you’re going to find a celebrity on SI, it will be here). Vine Street and 18-Bay Restaurant for special occasion fine dining. Marie Eifel Market for great sandwiches. And Maria’s Kitchen for authentic, casual Mexican food.
Where to Stay on Shelter Island
STAY: Ram’s Head Inn
The Rams Head Inn sits on a bulb of land separated from the rest of Shelter Island by a couple of narrow causeways. Prescient Real Estate agent, Joan Covey, built the inn as a resort in 1929.
At the start of the Great Depression, Covey enticed her Real Estate clientele in Great Neck, Long Island, to enjoy an island getaway for low cost; just a short drive from home. Although the inn has cycled through several owners and permutations, it still honors Covey’s original intent.
In 1979, Linda and James Eklund purchased the property, fixed it up and have been renovating as needed year after year.
First Impressions of Rams Head Inn
If ever you yearn for a lost-in-time shore experience, this place delivers.
A rambling, antique resort on an island (Big Ram Island) on an island (Shelter Island) on another island (Long Island), it takes a concerted effort to get to. But the property is so exquisite, you might not want to leave.
The lawn, peppered with white Adirondack chairs slopes down to a tiny cove beach from which you can kayak and swim in calm warm water. There’s a gazebo, a bocce court, corn-hole boards and tennis courts as well. In fact, you’ll find everything you’d need for a relaxing afternoon or two away from civilization.
The lobby is cozy and welcoming, with friendly staff, who will either take you right to your room or point you towards the popular bar. The comfy sunroom has the only television on site.
It’s easy, breezy, and with a stellar restaurant on the main floor, a self-contained resort. You never have to leave. Indeed, people come here just to read, reconnect, enjoy a good bottle of wine, and catch up on sleep.
Rooms at Rams Head Inn
Most of the 17 rooms are small but charming and bright. Beds sport white coverlets, furnishings include several antique pieces, and shear curtains allow in a good amount of sunlight.
Like many century old inns, some rooms have shared bathrooms. And a few feature private, albeit tiny ones. The whole effect is like your own personal cocoon.
Dining (See Above Under Where to Eat)
Rams Head Inn Amenities
Use of small sailboats, kayaks and SUP’s, as well as hammocks and chaise lounges are available, complimentary, to guests at the 800 ft. beach.
Regulation-sized Bocce Court
Private Dock for guests who come by boat located at the causeway.
In high season, shared bath $150 per night weekdays, $195 weekends, private bath $275 weekday and $325 weekends. Two bedroom suites $350 weekdays, $425 weekends. All include continental breakfast, wi-fi and use of property amenities. For offseason rates, contact the property.
STAY: More Shelter Island Inns
There are several other worthwhile hotels on the island including the renovated Chequit Inn, located in the “Heights,” Seven on Shelter – a classy “Boutique B&B,” and the Sunset Beach Hotel right on Crescent Beach – as close to a Hampton’s scene as you’ll to find on Shelter Island.