The portion of Skyline Drive north (west?) of Conklintown Road apparently dates to at least the 1930s, but the highest sections of the road which crosses over the Ramapo ridge from Oakland in Bergen County were built in the 1960s. Prior to that time, traffic, such as it was, could use the unimproved Tamarack Road and Cannonball Road to get to Conklintown Road. A vestige of Cannonball Road still exists in Wanaque, but most of it is at best a woods road in Ramapo Mountain State Forest.
The modern-day Skyline Drive, which remains treacherous and is often closed during snowy and icy weather, was built as a less environmentally intrusive alternative to the original plan to connect NJ 208 at its Oakland terminus (then US 202) with NY 208 at its Monroe terminus (old NY 17). A four-lane expressway was seen as both difficult to construct and potentially damaging to both the New Jersey Skylands region and the Sterling Forest region of New York.
Trucks are not permitted on Skyline Drive except for local deliveries. Partly for that reason, Interchange 55 of I-287 was built to provide access to CR 511, which runs through Wanaque, Ringwood, and West Milford.
| Mile | Street Name | Feature (South to North) |
| 0.00 | CR 692 BEGINS, Wanaque Boro | |
| 0.27 | Entering Oakland Boro, Bergen Co. | |
| 0.27 | Next 0.38 mile is Bergen CR S-91 | |
| 0.65 | Entering Wanaque Boro, Passaic Co. | |
| 0.80 | Entering Ringwood Boro | |
| 1.13 | Skyline Dr | Unnamed stream {culvert} |
| 1.30 | Skyline Dr | Unnamed stream {pipe} |
| 1.42 | Skyline Dr | Unnamed stream {culvert} |
| 2.43 | Skyline Dr | Unnamed stream {culvert} |
| 3.13 | Skyline Dr | Erskine Brook {bridge} |
| 3.35 | Skyline Dr | Greenwood Lake Tpk, CR 511 |
| 3.35 | CR 692 ENDS, Ringwood Boro | |