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OSR30

2026-03-28 · 29.32 mi · 3:35:57 · strava

Noah told me about this race by Orchard Street Runners, a running group in Manhattan I'd never heard of. They had a race — 30 miles around the perimeter of Manhattan — but checkpoints only. No set route or distance, you need a biker, unsanctioned and open streets. Running anarchy in the busiest city in the world.

This race was the perfect combination of being one month before my 100K, in New York, an ultra distance but not too far, and pretty unique. First race of the year and first race since CIM.

Scouting

Tuesday before, I did a bit of a scouting route. Took the Q up to 93rd and 2nd. Ran up First then over to Randalls Island, then back to First and up to 11th, over to St. Nicholas but missed the turn. Marked that as an important one.

Ran all the way up to the Hudson River Greenway — marked two more spots on the way to not miss. Ran up the Greenway to the top. Didn't run onto 10th but went all the way over to the west side. Hopped on a Citi Bike, went up to the top of the park where the second checkpoint was, then back down, all the way down next to the FDR to the GW. Didn't go under the GW but went up instead to the A. Scouting done. Verified a few spots that could be tricky but ready to go.

Sent Noah down on Friday to bike and scout the Lower East Side area after we gameplanned on Thursday with Mikey. Route mostly finished, ready to rumble.

Morning of

Woke up early for a cup of coffee.

Noah came by around 8:30, we prepped carb bottles, gels, gameplanned jackets, etc. Definitely a colder morning than expected with low 30's — the day had low 40's as the high but with windchill a good bit colder. We biked down to Orchard.

Orchard St. It was a zoo. Tons of people there, big lines for bib check. Bikes everywhere. Photographers everywhere. Peed, maybe twice, laced up the Alphaflys, and then got ready to go. Sadie and Noah's friend came down to the start too.

Bib 144. Someday I'll have a double digit bib, but it'll have to wait.

Shoes tight. Little jog to make sure they're laced right, then game time. Got a quick film photo with Noah before.

Pre-race with Noah
Pre-race with Noah

We moved to the start line, and next thing we knew bikes were let through to go out to the meeting points. I shuffled up to the 2nd / 3rd row in line. Let's rock.

Race

Race starts are usually chaotic, but this is maybe the most chaotic I've ever had. Joe was on a bike ahead of us waiting for the light at Delancey to turn green so we could blow through the intersection. Ready set go! The group went out fast. Sprinting down Orchard, we were dodging potholes and landed at Delancey quickly to a green light. We weaved and cut off a few cars turning left there then right on First Ave. I picked up Noah on the bike either here or at Houston and we were off. His bright yellow jacket made spotting him easy throughout the first half of the race.

The first mile was fast. 6:45 maybe? I couldn't believe how many people were ahead of me. Maybe 25 or 30? And I was getting passed left and right over the first few miles despite running 7-7:10's — about 30 seconds a mile faster than planned pace of 7:35's or so. It felt super low effort so we rolled.

Up First Ave was nice. I ran into Brooks and McKenna then shortly after Waters and Laura. We cruised for a ways, had some nice convos with a few people, got out some of the early twitchy nerves, then it was go time. Before we knew it we were at 96th, and time to turn. Noah and I had a plan (which looking back maybe wasn't the best?) but we turned on 96th then a left before the FDR up a side street to the bridge. Then we were up the bridge, and over the FDR. Most people crossed below then went up on the East River rather than on the other side of the FDR then crossing.

Over the FDR
Over the FDR

This went smoothly, we ran over to Randalls Island, picture on the compass, and first checkpoint done. A quick turnaround and back over the bridge to Randalls Island, down and then breaking uptown to 103rd. From here we zigzagged up to 110th at the top of the park — though it felt like more over and less up as we kept hitting lights and it took some time before we really made the move up in the top corner of the park. I had to pee at this point but decided to wait for a closer restroom. We went up on MLK and then over to St. Nicholas Ave diagonally up from 111th. We'd be on this all the way to 149th when we split right to St. Nicholas St then down to the Hudson River Greenway. This stretch went super smoothly and we were running with a relatively small group at this point — 5-8 runners and their bikers. Uphill, clicking blocks, we were at the Hudson River Greenway before we knew it. That intersection across was a bit dodgy, then the run down on the ramp was crowded with bikers and runners but pretty quickly it opened up and we were cruising on some of my favorite paths in Manhattan.

Once it flattened out I sent Noah ahead to find a bathroom and kept cruising, then shortly thereafter the eventual winner Joe DeAngelo passed me coming back down — he had doubled back and was running this way. He finished in 2:49:34, an astounding 5:35 pace. I kept up alone, took a right on 10th, then picked Noah up again who said there's a bathroom up in Inwood Park. Nice.

The section from here to Inwood was longer and steeper than expected. The roads were in bad shape so we took the sidewalk but it was a nice climb. Made it into the park, the path was clear and we found a bathroom right off the path next to the tennis courts. Went for a pee, came out and started running and WHAM!

I was coming around a corner out of the bathroom and a biker was coming back down. We made eye contact but I think each of us thought the other person was going a different side of the path and collided head on. I hit the ground but could tell right away most of the impact was on my jaw. My Alphafly was pretty cut up and my shoulder hurt too, but it was mostly jaw. I think we were both lucky not to be more injured. I was pretty shook (and I think he was too) but could tell nothing was broken and didn't have blood anywhere. I bounced up pretty fast and was running maybe 20-25 seconds later (cussing him a little bit). My jaw really hurt and we were only about a quarter mile from the checkpoint so ran up to the top of Manhattan under the bridge, took our picture, and Noah and I took a second to gather ourselves, check to make sure I was ok (he said it looked good at least), and about 30 seconds later we took off back down.

This whole time my jaw hurt pretty bad, but I could tell I was ok. It didn't hurt when static or opening my mouth, but I couldn't close my mouth at all. My molars weren't touching and had some pretty gnarly muscle knots in my jaw. Whatever. I was ok, had some adrenaline going, and figured it'd be ok. Off we went.

Running up next to the FDR my adrenaline wore off and I started feeling pretty bad. I knew we went out hard — had been averaging around 7:20's to this point, about 15 in — and wasn't sure how the rest was gonna go especially with my jaw hurting. This stretch I took a bit of Vaseline for my armpits as they were chafing, and also overtook on carbs as I felt a bit underfueled. After a gel and a lot of carb drink I was feeling much better by the time we turned down under the GW.

Back on the West Side Highway in familiar territory.

We just cruised this part. There were a few other runners here too — probably passing and getting passed in equal amounts. We were clicking off 7:15's though and it still felt great. Down the park, through where I run my workouts, and then about 3 miles from home (next to the cafe) I ran into Jason! He hopped in for like .6 or so and had a nice chat and took a nice picture of us. I wished he had run longer but he'd also done 12 that morning!

Then we continued down, cruising past the cruise ships and down into Chelsea. We didn't see any other runners for ages in this stretch except for one. Probably 3-4+ miles. We ran into Presley and Kaitlyn, and shortly thereafter Sadie, Abby, and Evan who were in town. I knew this spot was about 5 miles to go. Cruising. Still no other runners except one guy we had been chasing for miles who was about 100m in front.

4 to go. I turn to Noah — "We're not losing to this guy. No shot."

3 to go. No progress.

2.5... all the sudden a group of like 5-6 other runners appears in front of us including that one guy we had been chasing. It felt like that scene from The Princess Bride where the ship kept barely getting closer, but then all the sudden we were on them and I was part of the group as we approached the final checkpoint — the Staten Island Ferry. Noah had scouted and determined the best door was the far left so we could quickly skirt up Water. Sounds great. From the 100m to the door and then out we passed that entire group of 7 or so runners. Nice. 1.8 to go.

I was pretty non-verbal and working hard at this point. Low on carbs but could tell I had enough gas to push to the end. Noah scouted extra carefully here for cars. Under the Brooklyn Bridge a bit dodgy but we made it. Left turn, then right, then left onto Orchard. Oh shit. We made it.

Orchard was electric. As we're coming in we got lots of bystanders cheering. They cleared the path and a half block left. 3-5 deep on each side. Tons of cheering, photographers, etc. High five with Joe and across the line.

Finish
Finish

7:17 average moving pace (taking out the 2 minutes after the bike crash). Almost 20 seconds better than anticipated and a much lower effort. The whole stretch down the WSH was epic. Just cruising and clicking miles. I'm most proud of the end though — we closed in 7:08, 7:11, 7:11 and 6:26 the last third of a mile. Not bad for having a marathon in the legs and stopping for a picture in the middle of that.

Ouch my jaw hurt.

At the end we hung out on Orchard St for a bit watching some other runners finish.

At the end we hung out in the sun for a bit. Other Noah (who hit me with his bike) came by for a quick chat and to say sorry. We found some sun, got some food from the cafe, and started recapping the race. I couldn't really chew the sandwiches as my jaw hurt so much and grinding food was impossible without my molars touching, but I had a bit and some Coke. After about an hour we left and headed back for the house on Citi Bikes.

OSR30
OSR30

Thoughts

This race was cooler than expected. NYC running at its best. Underground but anarchy at the same time. We took over the streets for ourselves and had a day around the whole city. The NYC Marathon is the best day in New York. This may be the best running event though. Less crowds, more pure running. No medals or fanfare. Just you, a biker, a lap of Manhattan, and a ton of photographers.

If you have the chance to run any OSR races I would, but OSR30 specifically has a special place in my heart.

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