The 11th Annual Paine to Pain

Trail Half Marathon

October 7, 2018 (tentative)

Stupid-Cheap ($30) early registration for 2018 has closed.

Registration re-opens on Earth Day, April 22nd at regular-cheap ($50)


Final Results – 2017

Free Hi-Res Race Photos-2017!

Race Director’s Recap and Prize-2017

Race Reviews-2017

Thank You Volunteers!!!


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

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


133888-054-002hPaine 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: Through Oct. 20th (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.
        • $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 October 2nd 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?).

      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 2018 we may start donating some net proceeds to local charities since so much trail work has already been completed.

      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 2017 opened 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 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 October 3rd at 11:59 p.m.. 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 Sept. 1. For later 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.

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

      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). Please print and fill out this PDF registration form.

      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-ish (Mamaroneck), 7.5-ish (Saxon Woods golf club house, Scarsdale)  and 11-ish (Eastchester). If you need more water, or supplemental fuel, you better carry it.  There will 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 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.

      Please check the blog for updates!

      Our 2017 Sponsors:



      Supporting Sponsors:

      In cooperation with:

      2016 Results

      2016 Race Director’s Recap (and Prize!!!)

      2016 Race Reviews

      Free Race Photos!!

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