Song: "Carefree Highway"
Artist: Gordon Lightfoot
Peak position on the Cashbox Singles chart: #13
Number of weeks on the Cashbox Singles chart: 14
Weekly data:
| Week ending | Rank | Title | Artist | Label |
|---|---|---|---|---|
| August 31, 1974 | 88 | Carefree Highway | Gordon Lightfoot | Reprise 1309 |
| September 7, 1974 | 68 | Carefree Highway | Gordon Lightfoot | Reprise 1309 |
| September 14, 1974 | 54 | Carefree Highway | Gordon Lightfoot | Reprise 1309 |
| September 21, 1974 | 47 | Carefree Highway | Gordon Lightfoot | Reprise 1309 |
| September 28, 1974 | 41 | Carefree Highway | Gordon Lightfoot | Reprise 1309 |
| October 5, 1974 | 36 | Carefree Highway | Gordon Lightfoot | Reprise 1309 |
| October 12, 1974 | 32 | Carefree Highway | Gordon Lightfoot | Reprise 1309 |
| October 19, 1974 | 27 | Carefree Highway | Gordon Lightfoot | Reprise 1309 |
| October 26, 1974 | 24 | Carefree Highway | Gordon Lightfoot | Reprise 1309 |
| November 2, 1974 | 18 | Carefree Highway | Gordon Lightfoot | Reprise 1309 |
| November 9, 1974 | 15 | Carefree Highway | Gordon Lightfoot | Reprise 1309 |
| November 16, 1974 | 13 | Carefree Highway | Gordon Lightfoot | Reprise 1309 |
| November 23, 1974 | 28 | Carefree Highway | Gordon Lightfoot | Reprise 1309 |
| November 30, 1974 | 71 | Carefree Highway | Gordon Lightfoot | Reprise 1309 |
Rankings greater than 100 are from the Cashbox 'Looking Ahead' charts.