Pre-Read Caveat: I am still learning as an amateur runner. These are personal experiences and reflections on what worked (or did not) for me, not recommendations or training advice.
What Even Is Racetoberfest?
Last weekend, I completed my fourth race in five weekends to bring “Racetoberfest” home: my first ultramarathon (~50K), a trail half marathon, a solo virtual marathon, and a 5K.
My goals were to:
Complete four races in five weeks, including my farthest run to date;
Push myself and test my limits;
Stay healthy and uninjured;
Have fun!
My focus was primarily endurance rather than speed. More “party pace” so I could keep running week after week, less trying to set personal records (although ultimately, I did).
What started as a way to keep running after moving to NYC became a chance to explore my new home, find community, and explore my ambition. I wanted to reflect on how I got here, how I trained, and what I learned along the way.
Planning Reflection
Last December, I learned we would be moving to New York after my partner matched for a medical fellowship. That September, I had finished my first marathon: the Boulderthon in Boulder, Colorado. Shoutout to Shirley, Allison, and Sana for planting the idea, and to Allison for running the whole thing with me. And thank you to all the friends and family who came out to support!
I had also come to enjoy running as a way to explore Denver and Colorado more widely. I had complex feelings about the move and wanted to give myself something to work toward that would help me feel healthy, happy, and at home in NYC.
In the past, especially pre-pandemic, I had spent a lot of time in New York for work, but had never lived there. I could imagine falling into a routine of working a lot, then going out to eat, drink, and socialize without making enough room for the other things that energize me. I enjoy a good meal or drink out, but I know I feel better in both my personal and professional life when I spend time outside and work toward a tough physical goal.
So, about a month before our June move, I started looking into races.
I started with New York Road Runners (NYRR), which organizes the TCS NYC Marathon. I quickly learned that running in NYC is quite popular and signing up for races required more advance planning than I had accounted for. Their races looked amazing, but I thought I had missed my chance to join them that fall. (Thankfully, I was wrong. More on that shortly.)
The Running Threads and NYC Threads communities were excellent resources. After I posted asking what was out there, race organizers and other runners shared their favorites. Shoutout to Race Director Eric Turkewitz, who replied to me and suggested the Paine to Pain Trail Half Marathon!
I also dug a little deeper into NYRR, joined as a member, and signed up for their emails for upcoming races.
I think my race sign-ups went roughly like this:
Signed up for the Paine to Pain Trail Half Marathon after learning about it on Threads;
Heard about Race the Perimeter, thought it sounded fun, and signed up;
Signed up for the NYRR Abbott Dash to the Finish 5K;
Entered the NYRR virtual marathon lottery (Guaranteed Entry Tier).
That last one was significant. Through this lottery, NYRR offered a chance to earn guaranteed entry to the 2027 TCS NYC Marathon by completing a virtual marathon: one GPS-tracked run between October 24th and November 1st. I would still need to pay the entry fee for the 2027 race, but I would have a spot.
I assumed I had no chance, but decided to shoot my shot anyway. Then I got in!
Suddenly, I had four races on my calendar for October. At first, I thought I would have to drop at least one. But every time I considered dropping a race or two, I realized I just really wanted to do all of them.
So I asked myself: could I train to complete all four and recover between races and afterward without getting injured?
I took this question seriously because I had experienced foot and knee pain last year during training and after returning to running too soon after my marathon.
Luckily, both issues were minor. I suspected the knee pain was connected to older issues from my competitive fencing days and that worn-out shoes contributed to the foot pain. Those remain my best guesses; I never sought a professional assessment and the issues went away on their own.
The more I explored how to approach running four races in five weeks, the more feasible it seemed. I had several months to prepare, a decent running base from the previous year, and time to adjust my training as the plans came together. I expected a challenge, and I became excited to work toward this ambitious plan.
Which brings me to training.
Training Reflection
As a startup founder, I can easily spend hours (or days, weeks, even months) at my computer with very little movement aside from my fingers typing. Training for Racetoberfest pushed me to prioritize time outside, time in motion, and time to recover: eating, hydrating, sleeping, all of it.
I still worked a lot, but training gave me a reason to leave my desk. Even with the physical fatigue, I noticed that my thinking felt sharper and my mind clearer.
Last year, I trained for my first marathon in Boulder mostly alone, with the Nike Run Club (NRC) app and usually Coach Bennett’s voiceovers as my guide and training companion. That worked well for me, and I enjoyed the solo time.
This year, the biggest change was joining NYRR Group Training twice a week. “Turnover Tuesday” and “Tempo Thursday” gave me coaches, a community, and structure for my training, especially speed and tempo work.
I started getting a better sense of how different effort levels should feel and what paces I could sustain over different distances and durations. Even when I thought I was working hard on my own before, I had more room to push than I realized. Running alongside others helped me figure this out.
A couple of hours a week in Group Training, alongside solo recovery runs and mostly solo long runs, made a huge difference in how my race preparation felt.
I also joined a couple of Nike Project Moonshot long runs, which I really enjoyed, especially the long run from Brooklyn to the beach (Rockaway). They filled up fast, and the starting location required a train ride of 30 to 45 minutes, so I made fewer of these sessions than I would have liked.
I never joined a run club, despite their huge presence in the NYC running community. Several Denver running friends had encouraged me to join one long before the move, but a combination of scheduling and wondering whether it would be “for me” kept me from joining them. After enjoying group training so much, I think they were onto something.
I still love running solo. Now I realize I also enjoy running and training with others, and I want to make more room for both.
Another significant change involved tracking and technology: I finally bought a smartwatch. After much deliberation between COROS, Garmin, and Apple Watch, I landed on the COROS APEX 4 42mm.
Its focus on road running, trail running, and rock climbing appealed to me. Compared with tracking runs through the NRC app on the iPhone in my pocket, the watch gives me what feels like more accurate pace data, plus heart rate and other metrics I had never tracked before.
I do not want to become overly caught up in the numbers, and I am wary of wearing my watch all the time. But I appreciate having more information about my runs, and I am curious to see what else I can learn as I get better at interpreting the data.
I also added some mobility, stretching, and strength work, which I wish I had started earlier.
Around this time, I learned about ways to give AI tools access to my COROS and Strava training data through connections called MCP servers. I wanted to experiment with using that data to shape mobility and strength workouts, along with more personalized running plans.
I started putting together simple plans in October, toward the end of the training block, so I focused more on recovery than further training gains. I enjoyed the routines enough to put together plans for November and December, and I will likely make more once I settle on goals for next year.
I still have plenty to learn about the watch, the data, and how to use these tools to support my training. For now, I am enjoying the experimentation.
Race Recap: Race the Perimeter NYC
Race the Perimeter NYC kicked off Racetoberfest with my farthest run to date and my first ultramarathon.
The format is pretty neat: no road closures or fixed course, just a designated start and finish, three checkpoints where you take selfies, and a minimum of 31 miles along the perimeter of Manhattan. Runners can go solo or form a relay team.
In the spirit of testing my limits, I chose solo, although the relay looked very fun.
The organizers shared routes from previous years on Strava, but construction around Manhattan made figuring out which paths were open and where to detour one of the bigger challenges. I used my training runs, especially weekend long runs, to scout different sections and practice wayfinding.
This was tricky and also quite fun! Dead ends and detours added unexpected mileage to some runs. On one occasion, I finished my route exploration with a Citi Bike ride home.
The routes kept changing, too. One ramp to the East River path closed, reopened partially, closed again, and reopened fully around the race. Luckily, we found it open on race day!
Over the summer, I shared that I was considering the race on social media, and a college classmate signed up too. Go David! We traded notes during training and had each other for company on race day. This helped a ton!
I still got us lost a couple of times, either by following other runners or enjoying the conversation enough to miss a turn. But we caught both mistakes quickly and got far less lost than I had during training. I consider this a win.
I wore a vest full of fluids and snacks, which added more weight than I usually carried. I could have practiced running with it more often, but the extra weight mattered less given our relaxed pace.
We walked plenty of the uphills (Manhattan, you have a lot of sneaky hills) and took our time at checkpoints to refuel and rehydrate. By the time we finished, the cool, overcast morning had turned into a hot, sunny day. I was glad I brought sunglasses!
A few things I learned:
A mix of gels and easy-to-eat snacks worked well. Applesauce pouches, yum!
I aimed to fuel every four miles, though I ended up closer to every four to six miles, or roughly 40–60 minutes.
Water refills were essential.
Chapstick and sunglasses earned their space in my vest.
My headphones and portable charger did not. They came along for the run, but I never used them.
I loved discovering more of Manhattan, reconnecting with David (and meeting his amazing family at the finish!), and sharing the day with such an awesome group of volunteers and runners. Shoutout to the woman in the donut sweatshirt who forgot she had signed up and still crushed it and to the relay team celebrating a birthday in party hats all day long!
As an extra race-day challenge, I was also helping a friend’s partner plan a major surprise, with my run serving as the decoy. That meant keeping the race date quiet around friends and family who might accidentally spill the beans. A tough secret to keep, especially while preparing for Racetoberfest, but we pulled it off! The surprise went smoothly. Congrats, friends! You know who you are.
Completing my first ultramarathon still feels a little wild to write. I catch myself wanting to qualify it as “just” 50K or “just” an unsanctioned race around Manhattan rather than a mountain or desert trek. My parents, meanwhile, were pretty shocked at how far I ran. Their reaction was a good reminder to let myself feel proud. I covered a lot of ground!
I had a blast, and aside from a few lingering blisters, I felt like I recovered relatively quickly. I suspect the relaxed pace, plenty of food and water, and rest afterward all helped.
Race Recap: Paine to Pain Trail Half Marathon
My second race of Racetoberfest took me to the trails of New Rochelle, New York (not “upstate,” but outside the city and just a short drive or Metro-North ride away).
Towards the end of my time in Colorado, I discovered how much I enjoy trail running, even though I had only tried it a handful of times. Paine to Pain gave me a good excuse to get out of the city, hopefully catch some fall foliage, and explore new trails.
The morning started overcast and rain arrived just before I reached the starting line. If anything, the increasingly rainy weather added to the childlike joy of running through the trails.
The race also has a memorable start: people in Colonial-era attire fire muskets to send each wave off! There were also shoutouts for each wave noting runners who had traveled or who were local or hitting special milestones. I even got a mention, which felt pretty cool!
The well-maintained and well-marked course offered a fun mix of bridges, trees, grass, road, gravel, and everything in between. Compared with the Colorado trails I had run, the gentler rolling hills made it easier to find a rhythm and just run!
Volunteers cheered us on throughout the course. At one road crossing, a little girl cheering with her mom shouted at me, “You like doing hard things!” That made me smile. She had a point.
The local high school cheer team also cheered me as I neared the final stretch that led to a track finish, which was an awesome way to end the run!
I ended up setting a personal best for the half marathon distance, which surprised me given the trails, hills, and rain that eventually turned into mud.
Then I realized this was only my second half marathon race, both on trails. The first was RAM Party, which takes you pretty much straight up and back down a mountain in Colorado Springs. My previous fastest times over the distance came from training runs or stretches of longer races, including Boulderthon. It felt good to see what I could do over the distance and left me curious about how much faster I could go on a different course or in different conditions.
I rounded the track to the finish line pretty drenched and chilly, but was stoked and all smiles. I thoroughly enjoyed the post-race celebration. Bagels, nonalcoholic beer, what is not to love? My only regret: the hot pasta ran out before I got any.
Shoutout to Kellen for braving the rain to cheer me on! Prior to watching the start, we realized he had no practical way to follow me along the trails without a car. He spent the next two and a half-plus hours trying to stay warm and dry until I reached the finish. MVP!
A few things that worked well:
Carrying just enough gels and relying on aid stations for water. No vest, yay!
Bringing layers so I could decide what to run in. I chose a tank, which got soaked, but I suspect anything else would have just held more water.
Packing a waterproof backpack with wet wipes, dry clothes, and a raincoat for afterward. The wipes were clutch for getting the mud off!
Wearing a hat to keep rain out of my eyes.
Wearing my Topo trail running shoes, which handled the varied terrain well.
Next time, I would bring gloves and keep my layers on longer before the start. I got a little chilly waiting around.
I loved this race so much that I immediately signed up for next year. I did not know any other runners this time, but hopefully I will see some familiar faces for round two!
Race Recap: NYRR NYC Virtual Marathon
The virtual marathon had an unusual mix of solo-run freedom and race-day stakes. I could choose my own route and start time, but completing it would earn me a guaranteed spot in next year’s NYC Marathon. I wanted to get this one right, especially after a tracking mishap earlier in the year: I failed to record RAM Party for virtual race credit and ended up running a second half marathon the next day to make it count (reflected on here). An effective, if unplanned, introduction to running on tired legs.
Partway through the month, I realized October had five weekends. This felt like a small gift: a weekend without a race before the marathon and final 5K. My toes still had a few lingering blisters, and the break from racing gave them some time to heal.
I also joined the Proof crew for a really fun Sunday morning long run. Shoutout to Marco for getting me out on a cold morning I might otherwise have skipped! I was glad I went.
For the marathon itself, I headed out solo on a beautiful Saturday morning. I used Claude Code to help map a route that combined some favorite stretches of Race the Perimeter with part of the NYC Marathon finish. The result looked something like a giant upside-down cartoon “U”: around the upper perimeter of Manhattan, then into Central Park.
I enjoyed the route overall, although next time I would skip the Columbus Circle area. Between people admiring the fall foliage and runners previewing the marathon course, the park felt extremely busy.
At points, I had to walk or weave through the crowds, which mostly suited my slow-and-steady approach. I was particularly grateful that the tourist holding a large ice cream stopped just before veering directly into me!
This felt more like a really long long run than a race. The weather was perfect, I enjoyed spending the morning outside, and finishing felt especially satisfying with next year’s marathon in mind.
Race Recap: NYRR Abbott Dash to the Finish 5K
The Dash fell on Halloween morning, the day before the NYC Marathon, and gave us a chance to “dash” across the marathon finish line.
The race started outside United Nations Headquarters, within walking or jogging distance of home. Kellen had the day off, so we stopped at our favorite coffee spot for warm coffee and pastries, then walked to the start together. A pretty great way to begin race morning.
I wondered how many people would wear costumes. Some, though fewer than I expected! I also caught one of our amazing NYRR coaches at the start and finish (shoutout Noa!), along with a fellow Group Training runner doing a shakeout before the marathon.
My start wave separated me from the people I knew, so I ran solo. It was fast and fun! Running past the United Nations, Grand Central, and Times Square, then into Central Park in full marathon mode and fall foliage glory, made for a pretty special 5K.
By this point, I could feel the month of racing in my legs. I was glad to have one last chance to push the pace over a shorter distance before closing out Racetoberfest and giving myself time to recover.
My official time was 24:20, which I think (not sure) makes this my fastest 5K race.
My main logistical lesson: I had once again underestimated the scale of an NYRR race. Even the 5K before marathon day drew a huge crowd, which made it difficult for Kellen to spot me along the course or find me at the finish.
Other runners shared a tip I will use next time: agree on an exact meeting or cheering spot, down to the cross streets or landmark and the side of the course, using the runner’s left or right. “See you at the finish” leaves quite a lot open to interpretation.
Bonus: Spectating the 2026 TCS NYC Marathon
Last Sunday, I had the absolute joy of cheering on NYC Marathon runners! It felt like the perfect celebration to close out my own month of running and racing, especially with friends and Group Training partners out on the course.
Everyone warned me about glitches in the tracking app, and unfortunately, they were right. I think I spotted only about 30% of the people I hoped to see, but I still ended the day hoarse from cheering for friends and strangers alike.
Watching so many people work toward something they had spent months preparing for felt incredibly inspiring. I loved getting to contribute, even in a small way, by showing up and cheering them on.
I am excited to catch up with everyone who ran and hope to be out there with them next year!
Final Reflections
Racetoberfest was a success! I finished all four races, stayed healthy, and had a lot of fun.
The challenge was ambitious, but it also left me thinking I can go both farther and faster than I realized. Something to chew on as I consider future goals.
Hello, 2027!
I am grateful to everyone who played a part, in ways large and small: training partners, coaches, volunteers, friends, family, and strangers offering encouragement along the way. It takes a village.
Even with my focus on endurance, I set personal bests across several distances during training and racing. At least, the best times I have recorded! My running history includes plenty of untracked runs, a couple of Bay to Breakers races about a decade ago, and last year’s races in Colorado. Whatever the historical record, I enjoyed seeing progress beyond the distances I could cover.
Somewhere along the way, I also got more comfortable calling myself a runner. The label felt funny even while I was training for four races, but now it feels pretty straightforward: I run, I enjoy it, and I want to keep going.
Books, documentaries, and podcasts about runners and races also kept me company throughout training. If folks are curious, I would be happy to share some favorites.
What Comes Next: 2027 Adventures Mostly TBD
In 2027, I plan to work toward completing the NYRR 9+1 program for entry to the 2028 NYC Marathon, and hopefully run the 2027 NYC Marathon in November. I have also signed up for Paine to Pain round two.
Beyond that, I have no specific plans yet. For now, I am giving myself time to recover and think about what sounds exciting next.
I am open to suggestions!
Such an incredible achievement. This is so inspiring! Congratulations!