Phil and I completed the first documented end-to-end run of the O&W Rail Trail (that I could find) on 5/16/20. The posted time is an average of our two Strava files which differed by 5 seconds.
Our route started in Kingston at the northern terminus of the trail, behind the Super 8 hotel off Washington Avenue. The first 1.8 miles is minimally maintained grass and dirt before joining the paved path in Hurley. From there the trail continues uninterrupted, mostly crushed gravel footing, twelve miles south through Stone Ridge and High Falls. The trail continues just across Kyserike Road for about a mile before it joins Lucas Turnpike about 15 miles in. We continued south on Lucas Tpke to its southern end at Route 209, continued south on 209 for 3/4 of a mile to Accord; made a left on Towpath Road and an immediate right onto Scenic Road, for less than half a mile where we entered Veteran's Park and where the trail section resumes. After three miles of trail, we continued on Berme road for the next three miles to the next trail section, a short stretch that begins shortly after Berme Road crosses Foordmore Road and parallels the Rondout Creek for about 1.25-miles. We then rejoined Berme Road for nearly 2 miles, past the correctional facility in Wawarsing, and found the final 1.2-mile stretch of trail to finish at the southern terminus of the trail in Ellenville.
Initially the run was to be self-supported as we left one drop bag just before halfway containing water, Coke, and a candy bar. However it was converted to a supported run when I accepted some fluids from a friend of ours on his bike with a few miles to go. Phil technically used neither anything from the drop bag or our friend so would qualify as "unsupported" were it not for me accompanying him I suppose.
This was a relaxed training run and this time should be easily bested if someone is willing to endure the drudgery of 6-8 road miles to link up the non-contiguous sections of trail.