Give Me Shelter: The Harelegger’s Guide to Local Tourism


The windmill near Sylvester Manor on Shelter Island.

By Gianna Volpe

From the outside looking in, Shelter Island appears like a nut waiting to be cracked by the surrounding forks. But to those who know, love and see “The Rock” from the inside out, she’s far more a muse than a mystery — several times more special than may ever be explained in words. Though one can never be considered a true ‘harelegger’ unless born on the island itself, the real story of Shelter Island is tucked right inside its own name. During Pre-colonial times, the Native Manhanset called The Rock, “Manhansack Aha Quash A Womak,” or, “Island Sheltered by Islands.” The roughly 30 square mile chunk of land has remained exactly as such to this very day: a shelter for every conceivable configuration of the East End spirit. It’s a fiercely loved hide-away with an activity for every taste.

“Shelter Island is special because [even though] it has such a diverse population, everyone holds the island in the same regard,” Linda Eklund, the long-time owner of the Ram’s Head Inn, said of her beloved home from a high-top table at Star’s Café one rainy April afternoon. “Everyone wants to protect it.”

C.Y. Clark and the ferry circa 1906.


That includes Bill Clark III, the Shelter Island Town historian and great-great-great grandson of the South Ferry’s first Clark family patriarch, Samuel, who initially used a rowboat to transport folks between family properties on Shelter Island and the South side. The young Clark first began getting hands-on in the collection of his family history — and ultimately that of Shelter Island at large — after he first noticed the fabric of his family history beginning to fade. Clark has since traced his ancestors back to their English roots, far before his family began floating ferries full-time. Clark said the most surprising thing he’s learned since becoming the town historian has been how the tradition of true devotion to Shelter Island is one the Manhanset people share with their successors.

A view from the Mashomack Preserve. Jim Colligan photo.

Even after the turn of the century, the native people could be found living and loving the forever wild woods of what was then called “Sachem’s Neck.” The Nature Conservancy has since saved from development 2,039 acres of the peninsula’s interlacing tidal creeks, mature oak woodlands, fields and freshwater marshes — nearly one-third of the entire island — now known as Mashomack Preserve where even the newest visitors can learn to love Shelter Island between 9 a.m. and 5 p.m. as the property is open to the public for hiking purposes only, though the conservancy also organizes kayaking trips, truck tours and other hands-on activities throughout the summer. (More information is online at or at the preserve’s nature and visitor’s center just past the parking lot at 79 S. Ferry Road).

During a recent visit to the Mashomack Preserve to meet education and outreach coordinator Cindy Belt, and the preserve’s new director, Jeremy Samuelson, a fox stood outside the visitor’s center window clutching a squirrel in its mouth and proceeded to carry it back to what Belt believed was likely a hungry litter of kits.

These special chances to experience Shelter Island — a microcosm of the East End in its most relaxed form — are everywhere you turn, and they don’t begin nor end at the epic nature preserve. The education, adventure, history and innovation available on Shelter Island waits around every corner and the gate-keeping islanders are eagerly available to assist those pure in heart who are hoping to share in the discovery of the island. From craft beer to cow herding, barbeques, beaches, boats, epic events, preservation and celebration of the island’s past, present and future, what’s new on Shelter Island is as exciting as what has been there for centuries, such as the centrally located Sylvester Manor, which is now installing a state-of-the-art environmentally-friendly septic system this spring, and will unveil it at its “Women of The Manor” photography exhibit, which opens with a reception on Saturday, June 10 from noon to 3 p.m.

Getting There

The South Ferry. Glenn Waddington photo

Whether you’re coming from the North or the South, there’s a ferry waiting to get you on-island in two shakes of a lamb’s tail. Visit or for the respective summer schedules.

Current South Ferry Rates:

Passengers (either on foot or in vehicles): $1

One-way or same-day round-trip bicycle: $4 or $6

One-way or same-day round-trip motorcycle: $7 or $8

One-way or same-day round-trip vehicle: $14 or $17

Current North Ferry Rates:

Passengers (either on foot or in vehicles): $2

One-way or same-day round-trip bicycle: $3 or $5

One-way or same-day round-trip motorcycle: $7 or $9

One-way or same-day round-trip vehicle: $11 or $16

Don’t Do Me Like That: An Insider’s Guide To Avoid Acting a Fool on The Rock

Wednesday barbeques at The Pridwin. Photo courtesy of The Pridwin.

Don’t Do This:

Hop a ferry expecting a spot will be waiting when you arrive at The Pridwin’s Wednesday night barbeques. Manager Glenn Petry said the hotel’s weekly dining tradition, which began more than a half century ago for staffers, has become so famous an activity — particularly for those hailing from the North Fork — that folks are now, at times, losing the opportunity to attend the event. That doesn’t happen often, but nobody wants to show up to see the sailboat races, eat grilled tuna and listen to the Lone Sharks only to be turned away.

Do This Instead:

Call before you haul to assess evening traffic — particularly as the season progresses into Mid-July and August — or organize a group of 10 or more to reserve a table for your chance to see “Shelter Island and the North Fork get together for a party,” which is what Petry said the barbecues have become in recent years. “It’s a real destination for North Forkers and a point of pride for us that we’ve established this connection with the North Fork,” he said. “And for the first time in a long, long time, we’re going to be starting them in June — on June 28 — which is another fun fact. The group, ‘Magique’ will be opening it up for us.” This all-you-can-eat extravaganza runs roughly $40 for adults — half that for kids — including steamed mussels and clams, peel-your-own shrimp, grilled tuna, American salads of every sort, macaroni and cheese, corn on the cob, traditional barbecue items and brownies. Smoked meats may be new this year, so certainly keep those eyes peeled for brisket. Another tip: hotel guests start at 5:30 p.m., ahead of the arriving crowd, so consider a Wednesday check-in at Pridwin to get the most out of your visit. Don’t forget the lounge dance party after sunset.

Pepé Martinez at Star’s Café.

Don’t Do This:

Bring a coffee maker or Keurig for any overnight stay.

No matter where you overnight, whether it be at The Pridwin, Chequit, Seven or the House on Chase Creek — your Shelter Island stay is an invitation into the world of 2,000-plus people who not only protect the island like fierce and friendly ospreys, but share that space with three times their number every single summer, so caffeinating alone is ignoring a real possibility of adventure.

Do This Instead:

Go to Star’s Café and drink delicious local coffee with a local person, which won’t be a difficult accomplishment since many Islanders pretty much live there. In fact, Star’s beloved owner, Pepé Martinez, has a pup named Momo who could be waiting to greet you as well.

Pepé’s back-breaking industry climb as a Mexican immigrant fighting to overcome adversity on the East End led him to the place where he and wife, Lydia Martinez Majdišová, now run the Shelter Island Heights café with great coffee and an extensive menu of food. Star’s is an unofficial meeting and hangout spot for high-profile Islanders, who can also buy his fare at events like the Shelter Island 10K, which celebrates its 38th year on June 17. If you want to meet Pepé on that day, look for a guy with black curly hair and a big smile standing under a tent near the Shelter Island School.

Linda Eklund at Star’s Café.

Don’t Do This:

Disrespect, harass or annoy any year-round or second-home residents.

Remember, your vacation day may be seen as a violation to the peace and quiet sought by most homeowners living on Shelter Island — or worse, someone else’s work day — so mind body language and don’t take it personally should someone tell you to take a leap off Kissing Rock. Shelter Islanders generally spare what they can to others — particularly to those who are kind and lack expectation — so don’t be too afraid to open up.

Do This Instead: 

Check off your progress on this “Linda Eklund Ram’s Head Rec List for Day-Trippers,” garnered straight from the hotelier, who was found at Star’s alongside her husband, Jim:

  • A night of classical music with The Perlman Music Program
  • A hands-on historical excursion at Sylvester Manor
  • A cocktail at Salt’s come-as-you-are Shipwreck Bar
  • A get-dressed-up glass of rosé at Sunset Beach
  • A healthy hike at Mashomack Nature Preserve
  • A fishing day with Jack’s Marine Rods/Bait
  • A hammock nap at The Ram’s Head Inn
  • A round of golf at Goat Hill
  • A day at any beach*

 *$40 will net you a week’s worth of access at Shelter Island’s public beaches and town landings, including Wade’s, Shell and Crescent beaches, as well as Menhaden Lane and Fresh Pond Road.

Sailboats off Crescent Beach. Jason Penney photo

Don’t Do This:

Ask the Town Clerk for the location of “Sunset Beach.” I’m told Shelter Island Town Clerk Dorothy Ogar will quite simply respond that no beach exists by that name, because, um, well, it doesn’t exist.

It doesn’t exist, but Crescent Beach does. It sits across the street from the Sunset Beach Hotel and restaurant.

Do This Instead:

My grandmother always refers to Crescent Beach as being “Louis Beach,” (Louie’s Beach), which any proper islander would do, so if you must, ask Ogar for directions to “Louis Beach.” She’s far more likely to accept — and may perhaps prefer that — over fielding direction requests to “Sunset Beach.” Either way, you’ll earn more Shelter Island street cred.

Hole 9 at Goat Hill.

Don’t Do This:

The Gardiner’s Bay Country Club at 12 Dinah Rock Road is a challenging 18-hole golf course that was built between Dering and Cornelius Points in 1896, but it’s private, so those hopping the North or South Ferry for an impromptu round of golf will have better luck at Goat Hill. GBCC can count William F. Mitchell and Seth Raynor among its architects and the recently retired Bob DeStefano among those to serve as head golf pro.

Do This Instead:

Shelter Island Country Club — known to islanders as “Goat Hill” — is a nine-hole public course that was established in 1901 and can be found just across Dering Harbor from GBCC at 26 Sunnyside Drive. Goat Hill has a clubhouse located at one of the Island’s highest points and boasts a brand-new restaurant as of last year run by Sag Harbor’s own Peter Ambrose, so it’s an ideal place for newbies to grab a bite and enjoy a round of golf.

Those with munchkins might consider 3 Ram Island Road a more mandatory stop as Whale’s Tale sports an 18-hole mini golf course where even the tiniest tots can learn to enjoy Shelter Island, and boasts rentable tennis courts and an extensive ice cream selection for all ages.

Kissing Rock.

Don’t Do This: 

Make Quinipet Camp & Retreat Center a stop on your whirlwind tourist excursion unless you’re interested in learning more about the Methodist church. Camp Quinipet is a private camp, owned and operated by the New York Conference of the United Methodist Church, which has owned 25 acres on Shelter Island’s Northwest shore for more than 60 years.

Do This Instead: 

Follow Shore Road past beautiful Camp Quinipet to the beginning of Nostrand Parkway and instead of bearing left, continue down Shore Road’s Dead End to find the shore itself, as well as a large boulder that’s long been known to islanders as “Kissing Rock,” which has been painted over in recent years inviting folks to pay their respects to Army First Lieutenant Joseph J. Theinert, a Shelter Island war hero who sacrificed his life for his fellow soldiers in Afghanistan seven years ago.

Shelter Island 10K.

Don’t Do This: 

Count out The Shelter Island 10K if you’re a foot race fan. The Shelter Island Run is part of the Grand Prix series this year, making it the third of three great New York races, including the NYPD Memorial Run on May 21, Shelter Island run on June 17 and Cow Harbor on September 16, which will offer prizes to the overall winner in all three races. Following this year’s race, a post-race runners festival will start at 7 p.m. at the Island Boatyard and Marina, which includes dancing with DJ Twilo, local food trucks, cash bar, merchants, photo booth, kids’ fun area and raffle prizes. There’s a $10 admission for non-participants while runners and kids 14-and-under will be admitted for free.

Do This Instead: 

Sign up! The 10K race entry free is $40 — $50 on the day of the race — while the 5K costs $30, or $40 on race day. Kids 14-and-under run for $15 and veterans for free. Visit for more info about the event.

Quaker Sanctuary

The Island’s history is also deeply rooted in its service as a religious sanctuary,

sheltering Quakers from persecution and offering safe haven for services, which continue to this day at The Shelter Island Friends Meeting.

The Sylvester family — some Quakers themselves — began offering these religiously persecuted people refuge on Shelter Island after Barbados sugar merchant Nathaniel Sylvester first purchased the island for 1,600 pound of sugar in the mid-1600s. In 1884, The Friends erected for the first white “resident proprietor” a monument found in the historic Quaker cemetery off North Ferry Road, which tells their story through a series of stone tablets.

Community Supported Agriculture at Sylvester Manor

The Sylvester Manor Farmstand.

Sylvester Manor’s CSA serves as a successful model for community supported agriculture (CSA) programs that are operating from a number of farms throughout the East End. A CSA is a contract between a farm and its membership, which is offered produce weekly in exchange for money at the beginning of the season, as well as labor in the form of field work and distribution. The result is the ability for farms like that on Sylvester Manor to plan ahead for their season, and offer a sustainable, local food source grown without synthetic fertilizers, herbicides or pesticides. Members receive — in full or half weekly shares — between six and eight seasonal vegetables, including Heirloom tomatoes, radishes, zucchini, kale, summer squash, cucumbers, lettuces, beets, carrots, greens, leeks, garlic, beans and herbs, according to their website. 
Though the Sylvester Manor CSA is already sold out for the 2017 season, folks can sign onto a waiting list at 
Sylvester Manor’s executive director, Jo-Ann Robotti, said all those interested in buying produce from the Manor visit their farmstand, which operates through spring, summer and fall at the Windmill field at 21 Manwaring Road.

Visiting Mashomack

The Manor House at Mashomack.

The Nature Conservancy’s Mashomack Preserve Director, Jeremy Samuelson, gives his top five tips to those looking to visit the preserve.

  1. Jeremy Samuelson

    The Nature Conservancy’s Mashomack Preserve covers more than 2,000 acres spanning oak and hickory forests, seven tidal ponds, over 100 acres of open meadows and 10 miles of shoreline, covering roughly a third of Shelter Island. The Preserve is home to over 200 species of birds – including Bald Eagles — more than 20 mammal species as well as rare and protected plants.

  2. Mashomack has over 20 miles of walking trails and a paddling trail all open to the public and overlooking some of the most stunning vistas and landscapes on the east coast. The Mashomack Preserve and Nature Center are open seven days a week in July and August for walking, hiking, birding. The Preserve features accessible trails appropriate for all ages and abilities. A suggested donation of $3 per adult and $2 per child help protect Mashomack for generations to come.
  3. Guided kayak trips, full moon hikes, birding classes, truck tours of the furthest reaches of the Preserve, classes for young naturalist – these are only a few of the more than 30 programs The Nature Conservancy offers in the summer months – most free of charge. Each month also includes a new “Book-in-the-Woods,” where the pages of a nature-themed children’s book are mounted along a fully accessible half-mile trail.
  4. The Nature Conservancy’s expert naturalists work all year round with East End schools, Girl Scouts and Boy Scouts, nature clubs and other youth organizations to inspire the next generation of nature lovers. Mashomack Preserve also offers two week-long summer outdoor education programs for kids ages 8 to 14. Kids explore every corner of the park, learn about Shelter Island’s indigenous people and colonial history and work directly with The Nature Conservancy’s expert naturalists to understand the wonders that make up the preserve’s complex ecosystems.
  5. Mashomack Preserve serves as a “living laboratory” for Nature Conservancy scientists and researchers from leading universities and institutes. Ongoing research is helping protect and even improve the quality of Long Island’s tidal waters and helping identify nature-based solutions for the impacts of rising sea-level and other threats to coastal communities. Research at Mashomack Preserve is helping set the course for our region’s response to climate change.


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