A few years back, on a wind-whipped January day, a longtime seasonal resident stopped by the magazine office in Edgartown. She had summered on the Island for most of her life but had never visited in the off-season. She didnʼt like what she saw.

For her, the Vineyard has long been a patchwork of pink porches, green gardens, and Black excellence. Here instead were empty streets, shuttered restaurants, and miles of gnarled scrub oak. “This is my first winter visit and it will definitely be my last,” she declared. She didnʼt want to see her beloved Island outfitted in its drab winter coat.

I didn’t share her sentiment, but I understood it. Winters on the Vineyard are unfailingly gray, and even the biggest year-round booster will concede that they can be agonizingly long. Still, if you look beneath the surface, you’ll find that the Island is full of life, I explained. It is, in fact, when some of the most beautiful moments unfold. 

Each year, when the crowds depart and the to-do lists lighten, the hearty and fool-hardy twenty thousand people who stay behind start to slow down and settle in. We gather in libraries and gymnasiums and churches. We root for the home team. We lace up our skates and head to the ponds. We catch up with friends in wood stove–warmed houses. We patrol empty beaches in search of seals and snowy owls. 

We seek out and foster community wherever we can find it, whether thatʼs on a six-person row around Vineyard Haven Harbor or in an entirely volunteer-staffed greenhouse in Oak Bluffs. 

Summer gets all the attention around here, but the spirit of the Vineyard shines bright when the nights are longest. In the coldest months of the year, we create our own warmth.