| # | Clue | Answer As Given | Value | Round | Category | Air Date | Show |
|---|---|---|---|---|---|---|---|
| An official American Viticultural Area spanning multiple states includes this eastern island where you'll find the town of Chilmark | Martha's Vineyard | FJ | ON THE MAP | 2025-10-27 | #9421 | ||
| This resort island is named for a daughter of 17th century colonist Bartholomew Gosnold | Martha's Vineyard | $400 | J | POSSESSIVE GEOGRAPHY | 2023-05-16 | #12 | |
| This Massachusetts island was likely named for the daughter of explorer Bartholomew Gosnold | Martha's Vineyard DD | $2,000 | DJ | POSSESSIVE GEOGRAPHY | 2021-05-31 | #8411 |