This article revisits Labov's (1962, 1972a) germinal sociolinguistic work on Martha's Vineyard speech, providing a synchronic analysis of the /ay/ diphthong in words like right and time, and, in turn, a diachronic perspective on a sound change in progress. Labov observed that the first element of the /ay/ diphthong was raised in the speech of Martha's Vineyarders, particularly fishermen, and he correlated it with social factors like identity (i.e., local heritage) and resistance to summer visitors. The present authors provide a sociolinguistic analysis of /ay/ from a new set of data collected in a Martha's Vineyard speech community. The outcome suggests a change in the linguistic pattern observed by Labov, which the authors argue is linked to socio-economic restructuring and resulting ideological changes taking place on the island. The acoustic and social factors are analyzed using VARBRUL to show how /ay/ variation today patterns with various internal and external factors found to be salient in Labov's earlier study.