Ivan...
I pulled out my map box to see if I could learn anything more about this trail down the ridge south of Calaboose Creek. The following maps show no indication of a trail in that area at all:
1928 Santa Barbara NF Monterey Division
1934 SBNF Monterey Division
1939 USGS 15' Jamesburg Quadrangle
1940 Los Padres NF Monterey Division
1966 LPNF Monterey Ranger District
1984 LPNF MRD and SLRD
1987 LPNF Ventana Wilderness
1996 LPNF MRD and SLRD
But these maps below DO show it. The Kirk Fire map only shows a dotted black line (with no reference in the legend) leading up to point 4510 from the Piney Creek area, and stopping there. I think the WP map is based upon the current USGS dataset with little ground truthing involved.
1956 (revised 1984) USGS 7.5' Chews Ridge Quadrangle
1999 Kirk North Fire Map point 4510
2005 Wilderness Press Big Sur and Ventana Wilderness rec map
So if there was a trail there at some point in time, it seems to have eluded many of the cartographers. But like you, I wish some of the folks who have been around here for a real long time would pipe in shed some light.
Boon