| # | Clue | Answer As Given | Value | Round | Category | Air Date | Show |
|---|---|---|---|---|---|---|---|
| A segment of the Taconic Mountains is part of this highland area of Western Massachusetts | the Berkshires | $800 | J | U.S. GEOGRAPHY | 2026-03-02 | #9511 | |
| This hilly region of western Massachusetts is home to the Tanglewood Music & Jacob's Pillow dance festivals | the Berkshires | $1,000 | J | U.S. GEOGRAPHY | 2021-04-01 | #8369 |