The Race

16th Annual Paine to Pain
Trail Half Marathon!

Sunday, September 29, 2024 (tentative)

Registration for 2024 Opens on April 22nd

Free race photos for 2023 are here  (or via Facebook, here)

Race Director’s Recap and Prize-2023

Race Reviews (compiling now, so let us know how it went!)

“These are the trails that try men’s soles.”(sort of)
–Thomas Paine, The American Crisis, December 23, 1776

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.

A runner's legs splattered with mud

Many of the trails are completely hidden from public view and host a wide variety of wildlife including deer, fox, coyote, turtles, rabbits, hawks, owls, herons, wild turkeys, bald eagles (as of April 2021), and other critters.

Video: This video was shot by P2P veteran James Breen in2022, with drone photography by Ben Feinblum.

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 for 2024 will open on April 22nd.

Fees for 2024:

  • $45 Stupid-Cheap Discount: Three days only!!  
  • $55 Early Bird Discount: April 22nd – May 31st
  • $60 Runners Rate: June 1 – August 15th
  • $70 Dilly-Dalliers Rate – August 16th until we close online registration on September 24, at 11:59 pm.
  • We no longer do in-person registration.

There is a $10 discount for members of NewRo Runners and military veterans, good from April 22nd until August 31st.

Please remember that this race is a fund raiser to improve the trails. Starting in 2019 we started donating some net proceeds to local charities since so much trail work has already been completed. This included the immediate creation and distribution of 3,000 free masks by NewRo Runners and an additional fundraiser when the pandemic hit.

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

Volunteers: No race of this type happens without volunteers. If you’re not running, we need you on race day! Please sign up here!

COVID: Due to the enormous success of the vaccination program, the substantial decrease in severe illness, and that the event is outdoors, we suspended the vaccination requirement that we used in 2021.  Let’s all hope there aren’t any funky new variants that come down the pike. This is our COVID policy.

Registration and Timing: Online registration opens April 22 (Earth Day). Online registration only, through October 3rd. To avoid trail congestion, we start runners in multiple waves, just three minutes apart. (See: Chip Timing and Seeding)  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.  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 may be damaged in storms, or 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 others in safer spots.

Course Records: Men’s record, Matthew Baffuto (2022), 1:15:16. Women’s record, Shelbey Goose (2018), 1:28:35. Course records for all age groups, if you think you can snag one, are here: Course records and data.

Photo courtesy of Sport-Memories

Awards:  Once again, engraved tankards for overall 1-2-3. Awards are three-deep for age group M/F, except for 17-and-under and 70+

      • Overall (1-2-3)
      • 17 and under (winner only)
      • 18-29 (1-2-3)
      • 30-39 (1-2-3)
      • 40-49 (1-2-3)
      • 50-59 (1-2-3)
      • 60-69 (1-2-3)
      • 70+ (winner only)

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

Shirts and Names on Bibs: Shirts and bib names are guaranteed to those registering by August 31st. For later entrants, shirts will be distributed after the race depending on the number of no-shows that we have. And bibs, obviously, won’t have your name. In prior years we had enough shirts 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 must have ID to pick up your bib. These are the rules.  Your questions are answered there.

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 4-6:30 pm, or the Saturday before the race, from 10 am-4 pm.(Westchester Road Runner offers a 20% discount on clothes and 10% on non-sale shoes to registered runners. )

Pick up on race day is at the Thomas Paine Cottage Museum at 20 Sicard Ave., New Rochelle, from 7:00 – 8:30. Expect lines. This is the staging area for the race.

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: This race is semi-supported. There are only three water/aid stations: Miles 4-ish (Mamaroneck), 7.5-ish (Saxon Woods golf club house, Scarsdale)  and 11-ish (Eastchester). If you want a sports drink, gels, energy bar, etc., you should carry it. And dispose of the wrapper properly.

There will also be medical attention at each station courtesy of Empress EMS and a medical tent at the finish courtesy of Montefiore New Rochelle. 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 or 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. (Blind runners using a guide dog should contact the race director.)
      • 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.

Please check the blog for updates!

* We’re still calling it “annual” despite the year lost to the pandemic. Anyone that doesn’t like it can complain to my boss.

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

Our Sponsors for 2023





Supporting Sponsors

and in cooperation with

Eric Turkewitz, Race Director

Real job: