| # | Clue | Answer As Given | Value | Round | Category | Air Date | Show |
|---|---|---|---|---|---|---|---|
| One genealogist estimates around 90% of Kentucky's 1790 population had arrived there via this road | the Wilderness Road | $800 | J | HIGHWAYS & BYWAYS | 2012-04-03 | #6347 | |
| Part of this road was explored by Thomas Walker 19 years before Daniel Boone's 1769 explorations | The Wilderness Road | $200 | J | HIGHWAYS & BYWAYS | 1997-03-06 | #2889 | |
| Marked out in 1775, it was Kentucky's first road | the Wilderness Road | $300 | J | TRANSPORTATION | 1995-07-04 | #2512 |