Running from NYC to Boston

Timmy Zhou
Knowledge Foundation
14 min readJan 15


Day 1:

Route: Brooklyn NY -> Greenwich CT

First day! Going in, I didn’t really know what to expect, so I viewed it as just getting up for another run, except that I’d have to keep going for a week straight! I still had some packing to do, and wanted to make sure I didn’t have to poop while moving, so the day started relatively late around 9am.

My first crew stop with Christine (my gf) was 15 miles in, in the Bronx. I ran up Park Ave until 125th st and then got onto the Willis Ave Bridge to enter the Bronx where I continued up Grand Concourse. At 188th st I turned East. Most of this stretch was uphill and I ran it slowly since it was still familiar. I was about to go across the Bronx to Pelham Bay where there’d be some highways that I would be running next to, so I put on my reflective vest for the first time.

After this stop, the weather turned from sunny to cloudy pretty quick, and it got mentally tough too. This stretch was mostly running alone on paths cutting through the grass next to the Pelham Parkway. I felt alone for the first time and out of place. I think I was also getting sleepy even though I’d taken my sunglasses off. It was likely due to the early sunsets and not being accustomed to running later in the day. Once I passed Pelham Bay and ran over the bridge, it felt like the city disappeared and was replaced with woods and small suburbs. Over the week, I ran through a bunch of towns with strip malls as their center and didn’t find them to be very enjoyable.

Around 23 miles was the next crew stop at the edge of New Rochelle where I stopped to have some lunch which was a can of beans and chips. After that, I passed through New Rochelle which I didn’t really like either. Something felt off about the city, and I think it was trying to be like NYC, but was too spread out and empty in places. Once past New Rochelle, it was mostly following a sidewalk through a few towns until I reached Port Chester which was the highlight of the day. I remember during the stretch before thinking that these small towns weren’t as picturesque as I thought they were. Port Chester lived up to my expectations since it had a small village feel with some brick sidewalks and lots of shops. I ended the day running out of Port Chester and climbing a sketchy hill with no sidewalks on either side to make it into Connecticut!

Day 2:

Route Greenwich CT -> Milford CT

I wanted to begin running at around 8 for the rest of the week, so the routine mostly was to go to bed around 9:30 and get up just before 6. Two hours was enough time to eat, pack up everything, and 💩 (like 4–5 times). The first day was tough mentally, so it was a bit daunting during the first few miles of the day. I luckily played one of my favorite songs and it really helped to ease me into things. I passed by a small town with some river views, and then reached Stamford pretty soon after. Past Stamford was a bunch of suburbs with large houses (wealthy part of the state) that wasn’t very interesting to pass through, and it was a monotonous stretch from about miles 8 to mile 23 where the second crew stop was. The only exception was Norwalk which had that historical sea-side town feel to it.

Lunch was near a yacht club with a view of the ocean which I really enjoyed. After that until the end was really hard mentally for me. I passed through Fairfield, Blackrock, and Bridgeport before reaching Milford. Although there was “only” 12 miles left, usually not much trouble in training, during any sort of race even 1 mile can seem long. I fell into the trap of counting down the miles and how many hours I had left before I was done and that made things really really hard. This way of thinking makes each mile seem to last much longer and harder to enjoy the surroundings. There’s a screen on my watch that shows miles remaining until the end of the course and I felt glued to that information.

It was cool to pass through Bridgeport and see many of the same landmarks I’d only seen from a car or train before though! Finally I made it to Milford around sunset and was able to take a bit of walking break towards the end the appreciate the sunset while going over a small bridge.

In the hotel I was feeling really tired about an hour before bed, and definitely more sneeze-y/sick. I got sick in November, but with so much school going on the last week, it sort of came back. Day 1 was okay, but Day 2 definitely wasn’t as fun prior to bed. The day before I still felt pretty energetic after the run, so I was nervous what the rest of the week would look like.

The meaning of “One day at a time” finally clicked for me today though. Sometimes you understand the idea behind a message conceptually, but until you experience it fully, it doesn’t really click. As long as I can keep “surviving” each day’s distance and only focus on that, then after six tries, I’ll have completed the full journey.

Day 3:

Milford CT -> Killingworth CT

Two crazy things happened this morning. 1). I woke up and my legs felt fresh. I went to the bathroom in the middle of the night and things felt terrible, but a few hours later, everything felt brand new. I remember this being an occurrence that was common during my first year of running. Incredible what sleep can do! 2). My cold went away completely. I felt normal getting out of bed and my HRV value went up for the first time in weeks. With those two things going in my favor, I didn’t have any excuse to not be able to tackle the day!

The first 5 miles or so were harder than the rest of the day, since I was focusing on appreciating the distance I’d gone already and trying to forget how much more I still had to do. I was also thinking that I hadn’t really seen anything that noteworthy so far into the trip, and that’s when I reached the ocean. The next 5 or so miles were all right up against the coast, and that instantly brightening my mood and set the tone for the day. It was sunny and the water of LI sound looked great, plus there were some really pretty oceanfront parks that I crossed through too.

Soon after the the first crew stop, I was back in a more suburb-y area, but I was determined to keep a positive outlook and count the milestones going up (Half marathon, 20 miles, marathon, 50k etc). Reframing the distance covered by comparing it to a training run was definitely a good way to think about it. For example, 16 miles into the day meant that there was still 20 miles to go, but 16 miles would be a solid medium to long run normally. A little bit later I reached New Haven along the waterfront and finally got to see the food trucks next to the interstate up close. Each time I’ve driven past this section I always see those trucks with their colorful flags, and the ocean stretching out beyond. After New Haven I crossed a cool looking bridge with a house on top of it and crossed into East Haven. This was a ten-ish mile stretch of just strip malls and a boring state highway with small shoulders. There were some parts that were definitely pretty sketchy and I was surprised/frustrated that it was a two lane road, but the speed limit was 50 which meant people could drive up to 60mph. Some older drivers and teenagers got too close for comfort around corners and I fell into a funk.

For the rest of the day, it was running along the highway through really small towns and big stretches of trees. It wasn’t until the end of the day that I realized that this would be the norm through a lot of the country, and that I’d just need to adapt to this new challenge. I spent most of the afternoon feeling like it was really unfair that I had to run on these roads after always having a sidewalk for the first two days. By the end of the week, I’d accepted this as the norm and had come up with a pretty good way of handling things.

About a mile from the end I came across this awesome big waterfall around sunset and paused to take in the view. The shoulder was really narrow, so I had to climb outside of the guardrail. The day ended in a nature reserve on a dirt trail which was nice and quiet. I was looking forward to starting there in the morning.

Day 4:

Killingworth CT -> Norwich CT

The day started off along the same trail where I left off, and it was a really peaceful start to the day. The trail had some rolling hills and ran next to a lot of streams, it was a nice break to starting off next to a main road. I was a bit stiff around my ankles and the bottom of my foot which would come and go through the week, but didn’t really ever pose a problem once I started moving. Today would also be the most amount of climbing I’d have to do all week at around 2800ft, with two major climbs and around six miles of all downhill at the end.

The biggest lesson I learned today was the stoic concept of “Non-Striving”. After a good experience the previous day with trying not to look at distance remaining, I approached the day with a more relaxed attitude of not worrying about pace, and being okay with potentially finishing later. Appreciating small distance milestones was definitely the way to go, and accepting the reality that much of the land covered would be boring. Prior to starting, I’d assumed that it’d be a lot of quiet roads without cars, but often the way a road and surroundings looked at street level was pretty different than a satellite view. Listening to Dave Proctor on his Trans-Canada Speed Record (105km a day), helped put me in the right mindset that I’d need to finish the remaining days.

After the first 15 miles or so, the next 10–15 were windy mountain roads that went up and down with narrow shoulders. Traffic wasn’t too bad, but there were a lot of corners that I had to approach really cautiously, and that’s when I remembered some advice I’d gotten before about using a stick. I found one that was long enough and held it out the side whenever there was narrow shoulders or a blind corner coming up. The afternoon was quite nice, and it’d been sunny all day. I spent the time hiking up the big hills and running down them without any soreness which was great! My favorite time of day ended up being around 2–4 o’clock since I’d be past the middle point and felt like I had a lot of momentum behind me already.

The favorite part of the day was on the final climb, where the hill I was on was taller than the other ones around it and I could see above their treelines. At the top was open farmland which was really peaceful especially with the sun starting to go down and casting an orange light all over. By sundown, I still had around 3–4 miles to go unfortunately, since I’d had a slower start to the day and had the climbing to do. I was running the downhills at a much faster pace, and was still able to maintain good speed on the flat parts after as well. It got dark with about 2 miles left, but luckily there were street lights out, and there was only one dangerous stretch just before the finish. The route took me under an overpass for the highway, but even though it was a “road” it was right next to the interstate and had a lot of traffic coming on/off the clover shaped ramps. To get me to the other side of the highway, I had to walk down the street/ramp which had no sidewalk or shoulder and it definitely felt like the cars got too close. I was upset that the town/city had the audacity to put a stop light at the “intersection” I crossed at to get to the traffic facing side, as if it was aware that potential pedestrians would have to walk next to that many cars.

Day 5:

Norwich CT -> Scituate RI

I was hoping for a continuation of the past couple day’s positive streak, but the day ended up being much more of a mixed bag. I started the day really focused since it was the second most day of climbing, and I wanted to try and do an extra 5k. On day 6, I’d need to do close to 50 miles, and I wanted to try and chip away a bit at that. Not far into the day though, I had to get back on a state highway and could feel myself getting easily frustrated. I remember thinking that the highway felt so lifeless and barren and that there wasn’t anything interesting to see around me either. It was just the same forests that I’ve lived around my entire life. I was really close to the border with Rhode Island so I think I was trying to will myself to get there faster which made things harder mentally.

The only highlight of the morning was stumbling upon some farmland where there was a large herd of cows that I gladly spent 10 minutes or so sitting on the other side of the fence.

The border with RI ended up being 22 miles into the day, so most of the morning was spent in a bad mood, but I was re-energized for a bit once I crossed the border. In my mind, it felt like there was a shift in energy, but unfortunately it wore off a few miles into the state. From 22 to the finish there were a few miles were I got back into the flow of things, but also more frustrated miles of being in the same rural type of areas that was the same as Connecticut. The day ended next to a really large lake, but it was almost completely dark, and the bridge had no shoulders whatsoever. I didn’t feel comfortable next to the traffic and ran most of the stretch on the top of the stone walls on the sides. By the time I’d gotten to the other side it was completely dark, and since the road went through forest, there were no streetlights either and I realized immediately that I wouldn’t be able to see in front of me without a headlight. I waiting in a small field next to the road and decided to call it quits for the day around a half mile past the original stopping point.

Day 6:

Scituate RI -> Boston MA

Today ended up being the best day all week, and one of my strongest ultra performances yet. Once I reached Boston, I was getting picked up by my dad, but I had to finish before the incoming storm would arrive. This time pressure gave me a chip on my shoulder all day, and it was an awesome feeling.

I started running around 7:30 which was over an hour earlier than most days this week, but did not feel ready at all prior to getting to the start. I was thinking about the distance in terms of what I’d already been doing, but at least an extra 15 miles tacked on. Even on the drive to the start, I was thankful for any sort of delays because I just didn’t want to leave the comfort of the car, and spend another long day out on my own. The cold before the sun came up also didn’t help.

The first part of the run was at the base of a big hill that I hiked up, and it during this moment that I tapped into a quiet anger that helped fuel me during the first hour where I managed to do faster than 6mph and make it close to Providence. When I ran through Providence and reached the first aid stop, I’d been running my miles all below 11 min/mile which I hadn’t done since day 1. The ball of my left foot hurt at times like it’d been doing for a few days, but that would eventually disappear later in the day. This momentum allowed me to really stay in a focused state, and I just kept running and running for basically the entirety of the day, which is not something I’d been able to do in any past 50 miler.

Soon after Providence, I passed through Pawtucket and reached the border of Massachussets. I was still running very fast and wondered if this would be sustainable all day. In the back of my mind I knew I should slow down a bit, but at the same time I wanted to just go all out and see what would happen. I did pull back a bit on hills, but would be eager to run as much of a hill as possible after walking the steepest bits. On all downhills and flats I felt like I was flying. Knowing that there would be an end to the trip today, and having a lot of small towns/cities along the way to pass through really helped me take the route one chunk at a time.

The best part of the day was up until the marathon mark where I was running to Foxborough, but the large stretch between towns that I saw on the map translated into a decently long stretch along Route 1 when the sidewalks ran out. It was back to running close to traffic and just holding out a stick for safety. The third crew stop was just past Gillette stadium where I would then run through a few suburbs before finally reaching Boston. With 15 miles left, my pace slowed down a little bit as there were more hills, but from here on it was just running on sidewalks through nothing else really that notable. Once past the 40 mile mark though, I picked up the pace again and after just under two hours, I reached the sign that said “Entering Boston”.

The original goal was to try and make it to Boston Commons, but I wouldn’t be able to make it by the deadline I had, so I was hoping that there would be a sign at the city limits which there thankfully were! I went another couple of miles further to end near Roslindale on top of a big hill on Washington st that gave me a glimpse at the downtown skyline.

Main takeaways (notes for myself):

  • Non striving
  • Running through “bricking” after crew stops. Continuously moving forward “miles aren’t going to run themselves”
  • Survive each day — blinders
  • 35 miles a day definitly doable