A couple of weeks back I got added to a group chat by Tim Rossi, an absolute legend of a bloke, awesome runner and founder of the Lostboys Track Club. The other number was one I didn’t recognise. Tim wanted to link me up with Alex Burks, a Lostboy from upstate who was planning to not only run but win the OSR30.

For those not familiar Orchard Street Runners put on a bunch of highly competitive, un-sanctioned races throughout NYC. The OSR30 is a ~30 mile (48km) race with a course determined by each runner as long as they hit a list of checkpoints in a given order. As part of the race, each runner needed to have a bike escort tag along with them to be their navigation, moving feedzone, provide real time photos of the runner hitting the checkpoints and be their eyes and ears as they trek across the city. The checkpoints for this years race were as follows:

1. Start line - 50th street and Westside Highway

2. Entrance to Staten Island Ferry terminal

3. Under the Williamsburg Bridge

4. 60th and York at the John Finley Walk (pedestrian bridge)

5. The compass on Randall’s island side of Ward’s Island Bridge

6. Under the Henry Hudson Bridge in Inwood Park

7. Call for Help phone booth on the GWB

8. Fairway Market on the Westside Highway

9. Finish at “As Is”, 50th and 10th Ave

Alex provided some initial thoughts on the route and I did a recon ride the day before to test it out and make adjustments to ensure a smooth race day. This is the final route that I planned:

Of course after scouting the course in absolutely premium conditions on Saturday, the forecast showed constant rain for Sunday. I made my way up to 50th street, I was absolutely soaked by the time I met up with Alex. I hate riding in the rain, it’s miserable and usually I avoid it at all costs, but for the Lostboys I made an exception.

The race started off as expected with David Kilgore, another Lostboy and certified crazy man going full send from the very start. Some of David’s past feats include running back-to-back marathons in Rio in less than 6 hours and running 100 miles in a day in Florida heat to raise money for COVID-19 relief efforts. Alex settled into a nice pace comfortably in second place, his plan from the start was to run steady for the first 20ish miles before sending it for the final 10. For the first 4 checkpoints people ran mostly the same course, we crossed paths with David for the first time since the start on the Ward’s Island Bridge as he was coming back.

After Ward’s Bridge, there was a lot more variety in course selection. We opted to go straight across 119th to Saint Nick where most of the other runners zig zagged on the outskirts of the island. Our choice paid off as we were jumping on the Harlem River greenway, David was heading up the hill, so we had leapfrogged him!

Alex held a ripping constant pace from the greenway up to Inwood Park, once we ticked that checkpoint off I felt great navigating the rest of the course given my familiarity with it. We hit the GWB and ticked off the need help phone booth checkpoint.

After the GWB we followed the classic cyclist route back down to Riverside Drive and then skipped down to the greenway. A few other runners opted to continue down Broadway but we wanted to run uninterrupted on the flattest route possible. Alex really turned up the speed as we ticked off the 2nd last checkpoint on the Greenway before heading back to the race HQ. We felt so great, had planned a perfect route and didn’t get lost at all, we crossed the line absolutely elated. That’s when we got the bad news.

The organiser came up to us and said great run but unfortunately you went to the wrong phone booth on the GWB. We both thought the organiser was joking. Turns out he was very serious and we went to the Need Help phone booth instead of the Phone for Help phone booth. We were absolutely devastated given Alex won by over 14 minutes and the phone booth we needed to go to was an extra 200m up the bridge. Turns out second place also went to the wrong booth, so 3rd place technically took the win.

Despite the fact that we didn’t take the official win and after the initial disappointment had worn off, we were both really happy with the teamwork and race that was run. Maybe we run it again next year?