Around the Island

Jenifer’s Journal: Pirate season

‘Not all treasure’s silver and gold, mate.’ — Jack Sparrow (Pirates of the Caribbean)

It may not be printed on your Nature Conservancy calendar, but it’s the start of Pirate Season.

Though “high season” seems to run from Memorial through Labor Days, it’s been known to extend sometimes even through Thanksgiving. Indeed, the time has come to keep a sharp lookout for any pirate activity in the area, e.g., the sound of a three-masted galleon sliding by in the mist, strange warnings written in the sand, driftwood or stones configured into “X” shapes — that kind of thing.

I had some truck with pirates back a million summers ago on Silver Beach, but they didn’t re-emerge until a little over a decade ago when my older grandkids, then 4 and 6, stayed with me for two weeks in August, and my grandson found an ancient treasure map.

Ever since then, those insubstantial, semi-scary, but often silly, cutthroats have stayed in touch off and on with all my grandsons, granddaughters, nephews and nieces.

It’s not surprising, really. There’s a history of pirates sailing up and down this country’s East Coast all through the 17th and 18th centuries. All along the southeastern seaboard and all the way up the New Jersey coast were loads of them, including Edward Teach, the infamous Blackbeard.

In the meantime, Black Sam Bellamy was marauding about the waters of New England. And then, of course, there’s the East End’s own Captain Kidd, who buried a king’s ransom of treasure on Gardiners Island (now a part of East Hampton) in 1699, and gifted Lady Gardiner with a bolt of cloth-of-gold in thanks for her family’s “hospitality.” 

It’s said a piece of that 24-karat fabric resides at Sylvester Manor to this day. But if you look at Gardiners as a “treasure island,” it isn’t particularly prepossessing, any more than is the outline of the “map” drawn by Robert Louis Stevenson’s ailing stepson one August afternoon in 1881. The boy had begged his stepfather to write place names on that sketch and make up a pirate story to go along with it, all of which inspired Stevenson to write his classic, “Treasure Island.”

But have you looked at a map of Shelter Island lately? If any island is an archetype for a true “treasure island,” by rights it should be this one. For proof, the summer before COVID, my gang of grands hunted for and, after much suspense and sweat, finally dug up a treasure that would make any buccaneer’s heart skip a beat.

But Captain Sparrow is right: “Not all treasure is silver and gold.” For those of us who may not have seen our grandchildren in person in over a year and may be feeling a little rusty as the time for a much-anticipated visit from them draws near, this island is a positive treasure trove of timeless activities.

Aside from the sun, sand, sailing, and swimming, the library (, Mashomack ([email protected]), and Sylvester Manor ( all offer events, and/or tours that make them a great “grand” destination. And there seems to be lots going on at the Shelter Island Town Recreation Department. Check with the director Bethany Ortmann for details ([email protected]).  

At home base you’ll want to check your stash of board games — Checkers, Scrabble, etc. — and craft stuff: paper, markers, rock paint, etc. Make sure you have at least a couple of complete sets of playing cards. I know with my grand-kinder, for a couple of summers in a row, learning card magic tricks was big, not to mention Gin Rummy and War tournaments. 

In terms of “equipment,” I found walkie-talkies were a great hit with the 6-to-10-year-old set, and a Slip ‘n’ Slide, maybe, and I hear Croquet is making a comeback, so check the garage. But just in case you’re worried about running out of ideas (though you won’t), the internet is full of them, including a list of “101 Activities for Grandparents and Grandkids,” from washing the car to making “Slime.”

Of course, in a pinch, you can always suggest their creating that classic, the “lemonade stand,” though, as I recall, two hours sitting next to hot tar under a grueling sun feels a lot more like child abuse.

We’ve got this. In this 2021 “pirate season,” — particularly in the wake of COVID and their hours spent “remotely learning” in the glare of computer screens, we can help our grandchildren disconnect from them for a while and re-connect with us instead. No mates are better suited to one another than kids and their grandparents when it comes to seeking and finding treasure of all kinds, especially on this “Treasure Island.”