Oct 09, 2022 at 9:00 AM

Paine To Pain

Thomas Paine Cottage

New Rochelle NY, 10804


Entry Fee $35
(Lowest or Early Registration)

Entry Fee 2 $65
(Highest or Late Registration)

Prize Money: no


  • 13.1M

Series: Trail Mix

Type: Trail

Course Map: Download Map

Starting Elevation: 90

High Point: 250

Percent of the course on un-paved trails: 90%

First Year of the Event: 2008

Men's Record: Steve Crnic (2015) 1:21:27

Women's Record: Shelbey Goose (2018) 1:28:35


Paine to Pain is a giant single loop that winds its way through the woods and trails of five different lower Westchester parks. You never run the same trail twice and will spend 90% of your time on dirt (and rocks and roots) in the shade of the woods.

Many of the trails are completely hidden from public view and host a wide variety of wildlife including deer, fox, coyote, hawks, owls, heron, wild turkey, rabbit and other critters.
Where: Start/End in New Rochelle, just 4 train stops north of midtown Manhattan.

Course Overview: You should expect your time to be about one minute per mile slower than a road race. The first half is more technically challenging than the second half and will slow you down more than a minute/mile.

Staging area –> Thomas Paine Cottage in New Rochelle. Check this map for parking. Do not park in our staging area or on the course! There is easy taxi drop-off (corner of North and Broadview). You will find porto-potties, number pick-up, water and baggage check all next to the actual start line. The race starts in multiple waves to avoid trail congestion.

0.0 – 0.75 –> The race begins with a charge up Broadview Avenue, with a 1/2 mile climb at a 3.6% grade (almost 100 feet in elevation). This hill will spread out each wave before the first trail is entered.

0.75 –> 3.6 Our first wooded area is the Leatherstocking Trail, the most technically challenging part of the course. This is a 2.8 mile linear park that is often rocky and hilly. This trail brings us past Larchmont and into Mamaroneck. There are a number of wooden catwalks, some old and some new, but all of which are slippery when wet. Single file only on the catwalks and stay in the center, as running on the sides of them could jar loose a board and create a hazard.

3.6 – 4.0 –> A short, steep uphill road (8% grade) connection (Rockridge Rd. –>Deerfield Lane) will bring runners to Old White Plains Road and a small entrance to Saxon Woods. The first water/aid stop is on this hill.

4.0 – 6.0 –> After a twisty 1/4 mile section of single track built in 2005, we hit the main Saxon Woods trail and go right. (This is a deviation from the blue-star blazed Colonial Trail.) The P2P trail loops around the southern part of Saxon Woods, over a stream, through an area of boulders, and past a lake. We head north, parallel to Mamaroneck Avenue, along the park’s eastern border, across a driveway to the park’s camp ground and through a tunnel under the Hutchinson River Parkway. The Hutch bisects the park, dividing it into southern and northern halves.

6.0 – 7.5 –> The tunnel under the Hutch brings us to the northern section of the park. We skirt the Saxon Woods pool area (a prime spot for spectators due to easy access), enter Scarsdale, and then head west into the heart of this section of park. The 150-foot hill over rocky terrain is challenging. We exit the park by taking the trail next to the 18th fairway of the golf course and hit the second water/aid stop by the golf club house on Mamaroneck Road.
7.5 – 10.5 –> The race rejoins the blue-blazed Colonial Trail and heads west on the Hutchinson River Trail (our third park, an old bridle trail in the woods next to the southbound Hutch) through Scarsdale. There is a stream crossing with stepping stones.

10.5 – 11.5 –> We cross an entrance/exit ramp for the Hutch as we enter Twin Lakes Park in Eastchester. Our track will take us on a wide, dirt road running in the woods next to California Road. The third water stop is near the 11 mile mark, near the Twin Lakes stables.

11.5 – 12.5 –> After passing through a second tunnel under the Hutch, at the Eastchester/New Rochelle border, we emerge into Nature Study Woods, our fifth and final park. Much of this area was a former right of way for the New York, Westchester and Boston Railway. Some artifacts still exist in the woods. It’s a popular running spot for nearby Iona College and New Rochelle High School students.

12.5 – 13.1–> We exit the woods at Webster Avenue and Flandreau Road. The race finishes with a 1/4 mile run down Flandreau Avenue, entry into the football stadium at New Rochelle High School (McKenna Field), and a 3/4 lap spin on the track.

Recovery/Awards — Relax on the football field, eat food, listen to music, cheer on other runners, use locker rooms for toilets/showers, get post-race massage, reclaim baggage, watch children race around, visit sponsors and hang out for the awards ceremony.



Past Event Dates

Held on Oct 09, 2022

Held on Oct 10, 2021

Held on Oct 04, 2020

Held on Oct 13, 2019

Held on Oct 07, 2018

Held on Oct 08, 2017

Held on Oct 04, 2015

Held on Oct 04, 2015

Held on Sep 21, 2014

Held on Oct 06, 2013

Held on Oct 07, 2012

Held on Oct 02, 2011

Held on Oct 03, 2010

Held on Oct 04, 2009

Held on Oct 05, 2008