Here’s a minor provocation: Maybe end-of-year lists aren’t about the things being listed, but about the person writing the list. A few weeks ago I shared five books that shaped my experience of 2025, the point of which was mostly that I was shaped. In the lead-up to the list, I offhandedly mentioned making a separate list of excellent bike rides I’ve taken. I had not actually written this list down, but in the days that followed I began to wonder what it would look like, and whether it might be more revealing, and honest, than anything I could share about my reading habits.

I’m not honestly sure how many books I read last year, but I do keep pretty good records of where, when, and for how long I ride bikes. In 2025 I rode about six thousand kilometers by bicycle, for a total ride time of a little under three hundred hours. This was something like five percent of my waking life, but I’m pretty sure it consumed more than five percent of my attention and it almost definitely provided more than five percent of the catharsis I experienced. There are so many things I could tell you about my time on two wheels, but let’s get to the list itself — the format does, after all, have its virtues.

City Therapy, Brooklyn/Queens/Manhattan

I attempt to ride this route, or a variation on it, roughly once a week, though in reality I think I only did the full thing sixteen times this year. It is, in my opinion, a fantastic way to see New York City. I usually ride it on a road bike, but it’s pleasant on more or less anything. I often find myself tracing portions of it on my commuter, and rode a big chunk of it on my track bike, as a distraction, on Election Day 2024. The route travels a healthy mix of bike lanes and fully separated bike paths, and it meanders through a wide range of neighborhoods without feeling too circuitous. When I have time I like to find ways to extend it beyond eighty kilometers (usually by doing another loop in either Central or Prospect Parks), and every once in a while I’ll add a lap back and forth across the George Washington Bridge so that I can call it an interstate commute. No matter the details I love this route, and I recommend it (or segments of it, depending on your appetite) to residents and visitors alike.

It is maybe worth mentioning that the original purpose of this route (and the original meaning behind its name) was to give me some emotional breathing room after visiting my therapist’s office. At the time it, the office, was just south of Union Square, and after lying on the couch for fifty minutes I’d find myself riding up the West Side Greenway, then looping around Central Park, and over the 59th Street Bridge, before tracing the North Brooklyn waterfront on my way home. These days I normally ride the route in reverse, widdershins, with the bulk of the ride happening before my therapy session. This requires planning, and on-the-fly adaptability. I need to plan my work and family responsibilities around what ends up being a four-and-a-half-hour outing, and I need to be prepared for changes in the weather, and I need to deal with a fair amount of in-your-face New York City car traffic. One might think that these stressors would exert pressure on the ride, but I consistently find the entire door-to-door-to-door experience therapeutic, regardless of the weather and how the riding itself feels. Early in January, I rode this route on a cold, sunny Sunday a few days after it had snowed. The whole ride I was cautious; the streets were almost completely dry but still had a ton of road salt on them, and cornering became a bit squirrelly at times. Then, as I was cruising on a tailwind down the West Side Greenway, I was suddenly launched skyward by a foot-shaped wedge of ice that had welded itself to the asphalt. I was completely airborne, listing noticeably to starboard, soaring for a moment before landing hard on my right hip. My bike barely hit the ground, but I spent five minutes shaking myself off before I could continue. Afterwards I limped for days, and my hip became mottled with purple and yellow. Still I was happier, calmer, and I do believe stronger for having gone on the ride.

Sierraville to Downieville, CA

I’ve known about Downieville’s legendary downhill trail network for twenty years, and this route completely blew my expectations away. I rode it with Chris, in August, on my new hardtail, and since then I’ve been more or less constantly scheming about how I could do it again. The day previous I had ridden solo from Donner Pass to Sierraville (itself an excellent ride), ending at an Airbnb right next to Los Dos Hermanos and taking a soak at the hot springs before bed. On the Sierraville-to-Downieville day Chris and I awoke early, ate breakfast burritos at the little cafe in town, and then rolled along the southwest corner of the yellow-gold Sierra Valley before climbing a series of active logging roads over Haskell Peak. Then we descended to Gold Lake, hiked up the Round Lake Trail to a decommissioned portion of the PCT, and finally linked up, around lunch time, with the Downieville trail network. We flew down the Gold Valley Rim Trail, rumbled down “Baby Heads,” swooped alongside Pauley Creek and hung on for dear life on the Third and First Divide Trails. All of this riding was incredible and completely terrifying, and even sitting here months later I can barely believe I escaped without serious injury.

Better yet: At times I got the distinct sensation of having loosened my grip a bit, and of fully trusting the trails, and my bike, and my own physical ability. This is something I’ve found myself searching for, chasing, cultivating over the past few years — both on the bike and off of it. There are too many factors to worry about in life, too many subtleties to grok and study and manipulate. If I have any hope of making it through, I’ve realized, then I’ve got to learn how to play life a bit looser. I did this, for a few moments, while plummeting towards Downieville — and the sensation was utterly transcendent.

Goodwin Trail Loop/Laurentide Limit Day Scout, Connecticut

For a year or so I’ve been building a multi-day off-road route in Long Island and Connecticut, and early this spring I scouted a section of it. The section I scouted was just east of the Connecticut River, and includes what I believe to be the best singletrack of the entire route: the Richard Goodwin Trail. The riding was fun and the scenery was nice, and I enjoyed the opportunity to do a challenging downcountry mountain bike ride within an admittedly long drive from New York City. If I were doing it again and didn’t need to charge an electric car while I was riding, I might just ride the Goodwin Trail out-and-back rather than looping back on a mix of trail and asphalt. But even the paved sections of the route were pretty, and it was nice mixing the terrain (and vistas) up.

I rode this route on a Tuesday in July; on paper my productivity almost certainly suffered as a result. In this sense the ride was a manifestation of my decision to make time for the things that matter to me. Why a multi-day off-road route in Long Island and Connecticut matters to me, I do not know. But it feels like as good and healthy a side quest as could possibly exist, and if nothing else I think it’s worth allocating a few Tuesdays in July to side quests like these.

Bennington Covered Bridges Gravel, Vermont

This route, which begins and ends at a Hipcamp I stayed at for part of a week in October, was probably the best gravel riding I did this year. At fifty-eight kilometers it wasn’t all that long, but bathed in afternoon sunlight it was beautiful. Also, I think I had ridden a longer loop, around Glastonbury Mountain, the day before, and that included multiple chunky sections that I was still recovering from. Wanting to spend some time in the saddle but not wanting to overdo it, I made a compromise, and the result was this route — which includes two different covered bridges, both of which I believe use the “Town Lattice” truss design. Stopping to look at one of the bridges’ plaques, I learned that the Town Lattice was invented by someone named Ithiel Town. I recommend learning covered bridge facts like this one before you go out of your way to cross a bunch of covered bridges, lest you become one of the rubberneckers like me blocking traffic so that you can read the whole plaque.

Then again, sometimes it’s okay to rubberneck. I was there in early October, and southern Vermont was dozing through what seemed like the last week of meteorological summer. I had intended, initially, to ride the entire length of the state, catching an autumnal wave at the Canadian border and surfing it all the way to Massachusetts. But there were logistical hurdles to doing so, and in the end I camped out just north of Bennington and spent more or less equal parts of the week reading, writing, and riding asphalt, gravel, and Class IV roads. It was a compromise; it took effort; I enjoyed it very much.

XLI, Long Island, NY

I love, love riding the length of Long Island. I do it from Brooklyn (where I live now) to Southampton (where I grew up), and I very much recommend riding it in this direction, west to east, rather than the other way, which is fun every once in a while (I did it towards the end of summer) but tends to be less refreshing and more exhausting. On this year’s eastbound ride I added an additional North Fork loop, extending its length to more than two hundred kilometers and enabling some nice views over both Long Island Sound and Peconic Bay. This also meant taking both the North and South Shelter Island Ferries, neither of which accept credit cards — the only form of payment I had brought with me. Luckily my fares were lent to me by two different fellow cyclists, both of whom forgave the debt immediately and were totally lovely to chat with while on the ferry. While on Shelter Island I also had the great pleasure of receiving a free lemonade from a stand being manned by a couple of kids and their babysitter. By this point in the day it was late, and I was hot, and it was pretty lovely to come around the bend on a totally empty road and see a complimentary beverage just waiting there for me.

The thing I like most about this ride — perhaps the thing I like most about bike rides in general — is seeing the fabric of the island, and of the world, morph. For much of the route this change is gradual. Bed Stuy shifts to Bushwick, and Bushwick slides into Ridgewood. Long Island is almost entirely within the Census-designated New York Urban Area, and while riding its length one can really see an urban ombré, a dense environment fading into rurality. Pick any variable — sound, temperature, color palette — and as you ride you can watch the dial sweep from one end of the spectrum to the other. The result is both predictable and gently surprising. I believe this route was the longest ride I’ve ever completed, but I arrived at its endpoint more refreshed than tired.

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It being the holidays, and me being me, I’ve spent some time recently catching up with friends and family. Often they ask how my work is going, and often I’ve found myself giving complicated answers in response. Any clear-eyed observer would conclude that I’m obviously pretty confused about how my work is going, and I wonder whether it might be good to write down how I’ve been feeling about it, in the spirit of transparency and the hope of making some progress on whatever it is I’m working through.

So, here’s how I think my work is going. On the one hand, I believe that my job is to write and publish things, and at these two tasks I think I did a better job in 2025 than ever before. I wrote and published a lot of things, and the things I wrote and published were more deeply researched, more informative, and more honest than anything I’ve worked on previously. This is great, and I’m proud of it, and I’m excited to continue on this path in 2026.

On the other hand, though, my income has trended downward, significantly, for at least the past two years, and on some level that makes me feel like I must be doing something wrong. Every time I think about this I shudder a little. Then I steel myself, and re-resolve to follow what feels right, even when what feels right is to make a list of bike rides that meant a lot to me. I think all of this, each word reverberating in my head, shaking all of my insecurities loose. Then I take a breath, and sit back in my chair, and start planning the rides that, with any luck, will shape my experience of 2026.

A special thanks to SOW’s paid subscribers, who make literally all of this possible. They also get more: In this case full .gpx route files for each of these five routes. If you’ve got even a hint of curiosity about any of these routes, or if you just want to help keep SOW alive, you can support me directly by upgrading to a paid subscription today.

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