A Day on Fishers Island with Stories to Tell

Looking toward Fishers Island off the bow of Jim Larocca's Bojangles V. Bryan Boyhan photos

A conversation a year ago about cruising the New England coast and exploring the collection of islands that are tossed along the coastline — Martha’s Vineyard, Cuttyhunk, Block and Nantucket among them — led to a recommendation that I consider visiting Fishers Island.

Why would I, I wondered aloud. The island is all private.

Nope, came the response. There’s always The Pequot.

In addition to being the name of the Native Americans who once inhabited the south shore of Connecticut, as well as the name of the whaling ship (well, Pequod) in “Moby Dick,” it turns out The Pequot is also the local watering hole that slakes the thirst of islanders of all stripes — and then some.

But more on that later.

Fishers Island is one of those islands that stretch up from Long Island to Cape Cod. Sitting at 41.25 latitude and72.03 longitude, it is actually part of Long Island (Town of Southold) although it has something more of a New England vibe, and is physically much closer to Connecticut than the extremities of either Orient Point or Montauk Point.

So with the promise of a modest amount of pillaging and a cold drink at The Pequot, Jim Larocca, Jim Morgo and I ventured off on the first Jim’s 36-ft Grand Banks trawler for an overnight, bound for the Fishers Island Yacht Club.

A steady rain accompanied us for the four hour crossing with occasional breaks of simple gray skies. The sea was calm and we averaged about seven knots cruising out of Sag Harbor, around Cedar Point and out into Gardiner’s Bay, heading toward Block Island Sound and then Fishers Island Sound. Shortly after we passed the ruins at Gardiner’s Island’s North Point a small group of dolphins broke the water, feeding a couple hundred yards from the boat. Elsewise an uneventful trip.

The island stretches nine miles, from southwest to northeast, with a couple of graceful curves like a chubby snake moving up the coast. Approaching, we passed the uninhabited Gull islands, with their lighthouse and bird “condominiums” — actually large white boxes used in the research of the thousands of terns who call Great Gull Island home. Further on to the northeast was Race Rock and its light.

On an incoming tide, the water that rushes between the north ends of Plum Island and the Gulls, and the southwest tip of Fishers Island, travels north and northwest either through Plum Gut at Orient Point or The Race at Fishers. Together these sluiceways of water literally race in from the Atlantic Ocean and Block Island into Fishers Island Sound and ultimately travel to Long Island Sound. The Race is often beset with opposing winds, tides and current, making for a rollicking ride through sudden white caps, eddies and a roiling chop that can confuse the unsuspecting boater. It can be a lot of fun.

Docks at the Fishers Island Yacht Club.

The entrance to West Harbor, on the north side of Fishers Island, is guarded by North Hill and South Dumpling, which, along with its sister, North Dumpling, are a pair of tiny islands in Fishers Island Sound, one featuring a lighthouse reportedly owned and inhabited by the founder of the Segway.

We tucked into the harbor, sliding along Munnatawket Beach and around Hawks Nest Point. The Fishers Island Yacht Club sits in a well-protected cove and, although a private club, welcomes transient boaters.

Larocca has visited several times over the years and says there is much to recommend FIYC.

“The boating world is a community, and I always favor a place that treats visitors as part of that community, not just as commercial customers,” he said. “In the 25 or 35 years I have been stopping at FIYC, I have always found it to be very much in that spirit. Certainly a friendly and helpful staff makes a difference, as we experienced with two very nice young folks who assisted us; but when you are in a club — as opposed to a commercial marina — the attitude and friendliness of club members is always an added positive. On our weekend, members were chatty, helpful and friendly, and other boaters visiting the club were friendly as well. It really makes a difference.”

Hiking to town along Crescent Avenue.

The club docks are an ideal location to use as a base to explore the tiny commercial part of the island.

While it is true that the largest part of the island — about two-thirds — is in fact private, that means about a third of it is available for exploration. The eastern portion of the island was purchased by a private concern and developed independently decades ago, with large homes and a private golf club designed by celebrated course architect Seth Raynor in 1926. Its residents are members of some of the country’s blue ribbon families. DuPont is a name you might hear often. Aside from the club, there is little else to satisfy the appetites of society.

But in the western part of the island — in which West Harbor appears to be the center — there’s a gas station, a small market and a handful of retail shops that meet most of the needs of islanders, if not visitors, which those who live there either full or part-time seem indifferent about.

Morgo and I took the opportunity to stretch our legs and catch up after not seeing each other for more than a decade. The narrow streets curve and bend with lawns and gardens that stretch up to century-old shingle homes. Crescent Avenue skirts along the shoreline, turning from a paved road to a dirt road then back again. As the road bends, views open to offshore islands, sailboats pushing along the sound and Dutch colonials perched on bluffs.

Fans of “The World According to Garp” may remember the large shingled house featured in the movie. That home sits high on a rise on the island overlooking the sound where we had cruised earlier in the day.

We strolled past Hay Harbor and the club tucked along the cove. A dozen clay tennis courts were scattered around the grounds with young people dressed in their whites playing tennis.

‘Downtown’ on Fishers Island.

The little cluster of businesses are just about a five or ten minute walk from the docks of the yacht club. “Downtown” is really just a short street or two. On one side is the post office with a bulletin board plastered with notices about local goings-on.

Nearby there’s the Beach Plum, a sundries shop of sorts, with a colorful collection of housewares. There’s a jewelry store and a women’s clothing store and a gallery. A real estate office. And, of course, a bustling ice cream shop and a liquor and wine store, this one called the Drink ‘n Vessel.

Around the corner is the News Café, a deli where you can get a cup of coffee, and sit and read the paper at one of a handful of small tables outside along the street.

But our true destination was The Pequot — a left, a left, and another left from the clubhouse at the Fishers Island Yacht Club. In all about a 10 minute walk.

This is a convivial spot and nothing if not democratic (lower case “d”). It’s the place to rub elbows with the neighbors you never see all summer, and the landscaper who mowed your lawn or the girl who waited on you at the market. There are sailors and mechanics and titans of industry. And their families.

The place was filled on a recent evening with tow-headed children shooting pool or playing foosball while their parents chatted amiably at the long bar or at tables set across the back patio where a lazy string of white lights brightened the gathering dusk. The bustling dining/bar room was filled with couples on dates, and moms and dads feeding their little ones burgers and fries.

Inside at The Pequot.

You really don’t come to The Pequot for the food, we were warned; but it’s a place you’ve got to go to. And, frankly, there are no other options if you want a bite out with some friends on Fishers Island. But, the truth is, the menu is more than satisfying, with a range of choices from pub fare, like a double smash cheeseburger with a side ($15) and fish tacos ($15) to special choices like steak frites ($26), bone-in pork chop ($24) and a market price fish-of-the-day, which on this evening was sea scallops.

We opted for a couple of the house’s 14-inch wood fired pizzas: margherita and clam & garlic versions ($20). We started with salads ($13) and an oysters Rockefeller appetizer ($13), based on three tasty local Fishers Island oysters.

To wash the meal down we chose a local craft beer, a pinot noir and a Hemingway Margarita.

The restaurant is decorated rather eclectically, with an overriding nautical theme, i.e. colorful buoys hanging from posts in the dining room. There’s also a boar’s head sporting a pair of sunglasses keeping watch over the pool table. Graffiti appears to be encouraged.

Many of the people who work on the island come from off the island. Our waiter, for example used to commute from his home across the sound via a commuter ferry that leaves daily from Niantic, Connecticut. This year, he said, he chose to rent a place on the island. He’s only there for the summer, and said he and his girlfriend would take off after the season ends; maybe to North Carolina. There is a small year-round population, 236 according to the 2010 census, but that swells to over 2,000 during the season. And many make their way to The Pequot.

The dance floor at The Pequot.

Our waiter told us the mood of the place changes as the night moves on. There’s a small dance floor that looks like it is ‘80s vintage, with brilliant colored squares lit from below to light up the dancers. A sign nearby reads “Sam’s Disco.” Late night — or early morning — also brings some from the mainland who race over in boats to West Harbor to make last call.

The three of us tried our hands at a little pinball, and before leaving, finished off with a game of eight ball, and, for at least one in our party, a frothy Guinness from the tap.

And indeed, as we were walking out, we noticed the currents were shifting: the bustling crowd had thinned out, the children had gone home with their parents, and a man was posted at the front door to check the rising tide of late night revelers who may or may not be doing a little pillaging of their own.