7/7/14: Steve Herzberg of NewRo Runners organizes a weekly run on Leatherstocking or as Saxon Woods. Details on the WT Facebook page. It is in the morning mid-week. Steve says, “Very relaxed pace (10-12 minutes//mile). However, we encourage speedsters to run ahead and double back at the forks and we do the same for anyone running slower – no runner left behind.”
This is a strange trail. It is quite smooth in parts and quite rocky in others. Has a few tough hills. Among trails in the area, this is probably the most intense. It is very hard to do this easy. In parts of Mamaroneck, it has boardwalking.
It is part of the Colonial Greenway and connects to Saxon Woods at its northern end. This is a bit tricky, though. Here’s a map. You want to do it this way because Old White Plains Road is winding if you turn left onto it and without a shoulder. So it’s dangerous. Bottom line: when you get to Old White Plains Road, turn right for a few meters and then turn into the trail and make your way around back to Old White Plains Road.
OCTOBER 2015: Jenipher Quintanilla has a the blog Running the Path Less Traveled (and is the president of the 100 Half-Marathons Club). She posted the following video, which is a good sampling of the Paine to Pain course. The first trail one hits is Leatherstocking. I start it from the musket-shot, but there’s pre-race coverage before that: