Available distances
About
Test your limits at the Paine to Pain Trail Half Marathon, a top event in New Rochelle, in Westchester County, New York. Regarded among runners as one of the best trail half marathons in the region, this demanding 13.1-mile course draws competitors from all over eager to take on its technical terrain and take in the stunning scenery. Designed to challenge runners of every level, the event offers an energetic atmosphere and tough trails that promise both a physical and mental test. Experience the thrill of trail running on one of the most well-known courses in the Northeast.
Prepare for Paine To Pain Trail Half-Marathon with RunRun
An AI-generated training plan, adjusted every week based on your real sessions. Built around your goal, current level and race date.
- Personalized plan based on your VO2max, history and weekly availability
- Strava and Garmin sync: your sessions are analyzed and the plan adapts
- Target paces, long runs, key sessions: everything is calculated for race day
Races nearby
Other upcoming races around New Rochelle.
Helen's 5K Run/Walk
Sep 20, 2026 · Sands Point, NY · 6 mi away
3.1 mi
Summit Survivor Backyard Ultra at Kissing Bridge
Oct 3, 2026 · Yonkers, NY · 6 mi away
12 h
Palisades Half Marathon
Sep 27, 2026 · Fort Lee, NJ · 10 mi away
3.7 mi
Palisades Semi Marathon & 8K Trail
Sep 20, 2026 · Fort Lee, NJ · 10 mi away
13 mi · 5 mi
New Yorker Run
Sep 26, 2026 · New York, NY · 14 mi away
6.2 mi · 3.1 mi
Greenwich Half Marathon
Sep 27, 2026 · Greenwich, CT · 14 mi away
13 mi