Some of these photos appeared in a January 1953 issue of Life, but were infact shot in March of 1952 by stalwart photographer Alfred Eisenstaedt. They feature the slightly [ya think? -ed] bleak townscapes of Edgartown and Oak Bluffs, plus the mostly indoor pursuits of the island crowd. The closeup portrait is of Dennis Wortman, creator of the cartoon Mopey Dick and the Duke, about a couple of down at heel types.
Anyone can work a summer on the 'Vineyard, but takes mental toughness to winter over. We know a few that were almost broken by it... That was pre-internet times though, probably easier to feel connected now.