We summarize the primary records from more than 30 years of lepidopteran sampling across the largest of the southern New England offshore islands, Martha's Vineyard, Massachusetts. This island supports one of the highest concentrations of regionally unique or threatened Lepidopteran occurrences in the northeastern United States, including more than 75% of the ∼90 moth species formally protected in Massachusetts and Connecticut combined, perhaps the most intact moth fauna in the region associated with barrens, heathlands, and other sandplain communities. The array of first recorded regional occurrences and unique records of species previously believed extirpated, absent, or in decline throughout mainland New England includes: Lycia ypsilon (S.A. Forbes, 1885), Ptichodis bistrigata Hübner, 1818, Amphipoea erepta (Grote, 1881), Cycnia collaris (Fitch, 1856), Catocala pretiosa Lintner, 1876, Eacles imperialis (Drury, 1773), Eubaphe meridiana (Slosson, 1889), Heterocampa variaWalker, 1855, Metarranthis apiciaria (Packard, 1876), Phytometra rhodarialis (Walker, 1859), and Spilosoma dubia (Walker, 1855). Associates of grass-dominated and maritime wetland habitats in particular are overrepresented among species now believed extirpated from Martha's Vineyard itself, including Speyeria idalia (Drury, 1773), Digrammia eremiata (Guenée, [1858]), Pyrrhia aurantiago (Guenée, 1852), Papaipema stenocelis (Dyar, 1907).We explore the associations of threatened moths with various habitats in the context of regional decline, and emphasize the relevance of moth life history requirements to understanding their distributions across inland, coastal, and island barrens with varied ecological and land use histories.