Martha's Vineyard: Strategies: When to Go

“When I hear ‘shoulder season’ in connection with the Vineyard,” one resident told me, “I think of the shoulders of a football player.” The days where the “summer people” left promptly on Labor Day may be in the past, as the high seasons extends well into the fall, but generally speaking, spring and fall are calmer on the island than July and August, when the population swells from about 15,000 to 100,0000 and traffic becomes hellish.

On my most recent visit, I chose the week before Memorial Day, which turned out to be a great time to visit, since the weather was not too hot and the island remarkably empty (I had Menemsha practically all to myself). Most restaurants and shops had reopened, with one noticeable exception: Mad Martha’s, the venerable ice cream shop, which was still shuttered.