From an August 1988 column by Arthur Railton:

Okay, so you live on an Island. But that doesn’t make you an Islander. An island is geography — land completely surrounded by water. That makes the Vineyard an Island all right.

But there’s a lot more to being an Islander than just living on an island. Being an Islander is a state of mind, an attitude. Millions of folks who live on islands never become Islanders. Manhattan is an island, but New Yorkers are not islanders. Chappy is no longer an island, but folks who live there are Islanders. You don’t even have to live on an island to be an Islander. Henry David Thoreau didn’t and he was an Islander.

An Islander is someone who likes being outside the main stream, off the beaten path, isolated from the fashions and the follies of the continent. An Islander rarely complains about fog, dampness, mildew, moldy bread, stuck envelope flaps, damp sheets. Or standby lines. Or ferries running aground. Or high prices. Or hard-to-get-a-hold-of craftsmen. If he does complain, it’s with a knowing smile: “What do you expect, living on an Island?”

We all have promised ourselves during a stress-filled moment, “Some day I’m going to chuck it all and go live on an Island.” We weren’t thinking of Manhattan. Chappaquiddick, perhaps, but Manhattan island, never.

What’s the difference?

It’s a desire, a willingness, to swap convenience for contentment. Not every convenience, of course, but then you don’t get total contentment either. As you get more of one, you get less of the other. How you balance the two depends on you. Chappaquiddick or Martha’s Vineyard, two degrees on the Islander scale. Cuttyhunk or an uninhabited island in the Pacific, two more. Each of us must draw the line for himself. But it’s a pretty good rule of thumb: give up a certain amount of convenience and you get a certain amount of contentment.

Increasingly, we Vineyarders are refusing to give up anything. We want the convenience of the continent right here on our Island. Then we wonder why our contentment level is dropping. “The Island’s not what it used to be,” is the way we put it. Of course it isn’t, because we’re trying to make it less an Island by making it more convenient, but making it easier to get to and by demanding more continental amenities once we’re here. We’re acting less and less like Islanders and more and more like folks who just want to live near the beach. Islands are more than land fringed with beach tatting. There are miles of beaches on the edges of the continent. Islands should give us more than beaches.

It used to be that only true Islanders came here. It was too much trouble getting here for non-Islanders. Mainland beaches were handier. No ferries to wait for. Come and go anytime. Gradually, we raised the convenience level and non-Islanders began to arrive, on more frequent and bigger ferries. In faster and bigger airplanes. Land values soared and we all felt richer, but were we? When more folks got here, they needed more parking spaces, more shops, wider roads, more places to eat, more things to do. The bottom fell out of contentment. To protect ourselves from the hordes enticed here by the added convenience, we put up more No Trespassing signs. “Residents only” beaches kept us off cherished sand. No more walking across somebody’s field to enjoy a special wild beach. It was now owned by non-Islanders. No more access to tranquil ponds. Stickers, stickers, stickers. Those much-loved spots that we treasured were stickered shut. We increased the convenience of getting here and savaged the contentment of being here.

We’re trying to have it both ways. And it won’t work.

In January 1857, 131 years ago, during a long cold spell, Vineyard harbors were frozen solid for two weeks. No boats could arrive, none could leave. Scores of coastal schooners were frozen in Holmes Hole. The ice-bound skippers got itchy and collected a purse of $29 for anyone who would “proceed to the main to carry letters and procure what news could be had.” Vineyarders didn’t put up the money. Isolation did not bother them. They were Islanders. But the visiting mariners couldn’t take the quiet.

Three Vineyarders, then as now eager to make a buck from visitors, accepted the challenge. They pushed a skiff across the ice to open water and started rowing for Woods Hole. By dark, they made it to Naushon. In the morning, they reached the main. The following day, they started back, carrying what little news “could be had” in Woods Hole. A strong northeasterly drove them down to Tarpaulin Cove where they spent the night. They got back to the Island the next day and picked up the $29.

That was 130 years ago when all Vineyarders were Islanders. Being isolated was no burden. Remoteness was part of Island life. Today, we’re frittering away that insularity. We’re bulldozing the contentment many of us cherish. It’s time to lower the convenience level.

Compiled by Alison L. Mead