I ran the 5 Sisters loop today in just under 3 hours which to date is the second fastest overall time, and the fastest female. I ran about 9 miles of the loop with my friend Michael Guillorn as the goal of the day was to run under the mixed gender category. I lost site of him going up Dundenberg and pushed on ahead. I hit the ice rink parking lot just under 3:00, and he came in at 3:11. I'm unclear how I'm supposed to submit this given the time discrepancy...
I made a minor navigational error at mile 12 and turned onto a single track that parallels Doodletown Road/Dundeberg Turnpurnpike. According to the NYNJ Trail conference map this is the actual 1777W trail and seemed like the correct choice at the moment, but it is a variation from the .gpx file on this site and the Strava segment. It accounts for .02 mile less change, equal vertical gain/loss but is less runnable so seems like a wash.
This is a fun and beautiful route. It's filled with great views, technical rocky descents and climbs that is classic Hudson Valley, and some really runnable single track and wider sections. The majority of the elevation is front loaded, but the hills keep coming throughout. I've been in this area a good handful of times the past year and generally knew the route by heart so navigation wasn't much of an issue and something my friend really excels at. There are lots of unmarked trails and slight variations and bypasses to make wrong turns on. I was able to refill my water in the creek at mile 8.5, but this is often dry during the summer.