The following are past Climb to the Clouds record holders and their recorded times.
Note: The records set in 1899 and 1903 were prior to the first official Climb to the Clouds, which was first held in 1904.
| YEAR | DRIVER | CAR | RECORD TIME |
| 1899 | F.O. Stanley | Stanley Locomobile | 2 hr. 10 min. |
| 1903 | L.J. Phelps | Phelps | 1 hr. 45 min. |
| 1904 | Harry Harkness | Mercedes | 24 min. 37 3/5 sec. |
| 1905 | W.H. Hilliard | Napier | 20 min. 58 2/5sec. |
| 1923 | Ralph Mulford | Chandler | 17 min. 0 sec. |
| 1928 | “Cannonball” Baker | Franklin | 14 min. 49.6 sec. |
| 1930 | Ab Jenkins | Studebaker | 14 min. 23 sec. |
| 1932 | “Cannonball” Baker | Graham | 13 min. 26 sec. |
| 1934 | Al Miller | Hudson | 13 min. 20.6 sec. |
| 1935 | John C. Reuter | Ford Special | 12 min. 46.4 sec. |
| 1938 | Lemuel R. Ladd | Ford Special | 12 min. 17.6 sec. |
| 1953 | Sherwood Johnston | Jaguar | 10 min. 47.6 sec. |
| 1954 | Sherwood Johnston | Jaguar “C” | 10 min. 44.8 sec. |
| 1956 | Carroll Shelby | Ferrari 375 GP | 10 min. 21.8 sec. |
| 1961 | Bill Rutan | Porsche Special | 9 min. 13 sec. |
| 1990 | Tim O’Neil | VW Rally Golf | 7 min. 45 sec. |
| 1991 | Paul Choiniere | Audi Quattro | 7 min. 9.61 sec. |
| 1992 | Frank Sprongl | Audi Quattro | 7 min. 8.61 sec. |
| 1993 | Paul Choiniere | Audi Quattro | 6 min. 46.62 sec. |
| 1995 | Paul Choiniere | Hyundai Elantra | 6 min 45.22 sec. |
| 1998 | Frank Sprongl | Audi Quattro | 6 min. 41.99 sec. |
| 2010** | Travis Pastrana | 2010 Subaru Impreza WRX STI | 6 min. 20.47 sec. |
| 2011 | David Higgins | 2011 Subaru Impreza WRX STI | 6 min. 11.54 sec. |
**Unofficial: Pastrana’s time was set during a private run, outside of Climb to the Clouds competition.