Paine to Pain Logo

The 9th Annual Paine to Pain

Trail Half Marathon

Sept. 25, 2016 (tentative) — Gunshot @ 9 am

“These are the trails that try men’s soles.”

–Thomas Paine, The American Crisis, December 23, 1776 (sort of)


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.

Start at Thomas Paine Cottage, New Rochelle, New York. (map). End at New Rochelle High School. (Both at the intersection of North Ave. and Broadview Ave.)

Click the map for a large, printer-friendly view of the race track.
Paine to Pain Race Track

Registration fees (this includes the service fee for our primary registration company, NYC Runs):

    • $30 Stupid-Cheap Discount: Oct. 21 – 23, 2015 (at 11:59 pm). Risky signing up a year in advance? Yes, but worth it! For those who will rearrange their schedule to run this puppy. [Register here]
    • $50 Early Bird Discount: April 22nd – May 31st.
    • $55 Runners Rate: June 1 – August 15th
    • $60 Dilly Dalliers Rate: August 16th until we close online registration on September 23rd at 11:59 pm.
    • $65 Wussies Penalty Rate: Close of online registration to race day, if available, for last minute sign-ups (waiting to check the weather report?)

Please remember that this race is a fund raiser to improve the trails.

See our No Refund / No Exchange policy. It tells you why we do what we do. And this is the race cancelation policy. Do they both suck? Yes. But at least we explain why we do what we do.

Registration and Timing: Online registration for 2016 opens for 3 days only October 19 – 21 (11:59 pm), then re-opens April 22nd.  For in-person registration on race day (if available), please fill out pages two and three of this form and bring it with you. To avoid trail congestion, we start runners in multiple waves. (See: Chip Timing and Seeding) Online registration stays open until September 28th at 9 pm EDT. There is a 3-hour time limit on finishing (see below).

Minimum Age: Those under 18 need written parental permission. (And frankly, you should also check with your high school athletic coach.)

Risks: There are plenty of risks of running this event that we like to consider features of the trail and the race. Whining about trail conditions is strictly prohibited. Boasting is allowed. You should read about some of the risks here.

Catwalk Risks: The Leatherstocking Trail (miles 0.75 – 3.6) has a number of wooden catwalks, whose condition varies with their age and the weather. Boards can become damaged in storms, or simply jarred loose by other runners. They are also very slippery when wet. Please stay in the center of these walks and do not pass while on them. Bide your time. Cool your jets. You’ll have more than ample opportunity to pass other runners in safer spots.

Course Records: Men’s record, Matt Walsh (2011), 1:21:35. Women’s record, Deanna Culbreath (2012), 1:31:42. Course records for all age groups, in case you think you can snag one, are here: Course records and data.

Photo courtesy of Sport-Memories

Awards: Awards are three-deep in the following categories, for men and women

  • Overall
  • 29 and under
  • 30-39
  • 40-49
  • 50-59
  • 60+

Age group awards are based on chip time, but Overall 1-2-3 is based on who crosses the finish line first. So if you think you can snag first, second or third overall, contact one of the organizers to assure first wave placement.

Shirts: Shirts are guaranted to those registering before e-registration closes on September 30th at 11:59 pm. For late entrants, shirts will be distributed after the race depending on the number of no-shows that we have. In prior years we had enough for everyone. This year? Who knows? Want to make sure you get? Don’t wait until the last minute to register.

Bib/Packet Pick-up: You are strongly encouraged to pick up your race packet in advance at Westchester Road Runner at 179 E. Post Rd. in White Plains, NY on the Friday before the race, from 5-8 pm, or the Saturday before the race, from 10 am-4 pm.  They will offer a 20% discount on all non-sale shoes and clothing to bib-bearers. Packets will also be available race day from 7:00-8:30 am at Paine Cottage (race start area).

Baggage Drop: Available right by the start line, and bags will be brought to the finish. Please don’t leave valuables in the bags as we are not responsible for them.

Aid Stations: There are three water/aid stations: Miles 4 (Mamaroneck), 7.5 (Saxon Woods golf club house, Scarsdale)  and 11 (Eastchester). If you need more water, or supplemental fuel, you better carry it.  There will be medical attention at each station, courtesy of Sound Shore Medical Center. There will be toilets at the start, mile 7.5 and finish.

Time Limit / Street Closings Security and volunteers are discharged based on a three hour finish, as timed from the start of the last wave. After that, you’re on your own. This is not a race for walkers.

Estimated finish times: Approximately one minute per mile slower than a half marathon road race. (Course description and elevations here)

Trash: Please hold used gel packs and energy bar wrappers for one of the trash cans at the water stops. We do not have a clean-up squad to pick garbage up off the trails.


  • No dogs: Sorry, but they are a tripping hazard on narrow trails and not permitted in the finish area either.
  • No headphones: Sorry, but people must be keenly attuned to those around them that might need to pass on narrow trails.

Parking: If you are unfamiliar with the area, please click on this page to look at our map of available parking areas.

Public Transit from NYC: It’s easy to do. Click this link for details on getting to the race by train.

Best Spectating Spot: Not to worry. We got you covered. Click here for the easiest spectating spot around.

Kids: We have a free one mile kid trail race that starts at the high school across the street and uses the trail around the twin lakes in front of the school (therefore, no strollers). This will start around 9:30 after the last wave of the P2P goes off at 9:20.  Please register your kid(s) online. The event will be supervised by the Tailwind Track Club, a Westchester based youth running club.

Links for 2015 Race:

Race Director’s Recap

Race Reviews from Our Runners


Thank You Volunteers! 

Free Race Photos!!

Mother Nature, That Was Your Best Shot?

A Continuing Thank You to our 2015 Sponsors:




Supporting Sponsors:

In cooperation with:

Please check the blog for updates!

2014 Race Directors Recap is here

2014 Race Reviews

2014 Race photos are here

Contacts: Might as well go to the contacts page for that, right?