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. I had not run here in years, but I visited on Dec. 12, 2015. Lots of boardwalk has been added and I found it not be well marked; it is part of the Colonial Greenway, which has blazes to mark it, but they were absent at least to my eyes in numerous crucial spots. So yiou may find yourself running down a deadend, which is part of the fun of trail running.
Because of the terrain, especially in the southern, New Rochelle portion, this is not a trail for a relaxed run. Your strides will constantly be clipped (and you may walk through a particularly dicey stretch early on) so it is very hard to get into a flow of a run. This helps explain why Paine to Pain is so tough. Trail runners will savor these stretches. Roadies will not, but they will enjoy a tough workout.
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: