Bear Mountain

Date

April 18, 2026

Distance

61.15 miles

Location

New York

Strava Activity

https://www.strava.com/activities/18165358909

So the other day, I said that I’d go on a bike ride with Kevin. I eventually decided to bail (I know, I know) for a few reasons: first, from what I could tell, the itinerary looked a bit ambitious for my current level of cycling fitness; it would have been both a good amount longer and a decent bit faster than I have been riding recently. Second, I hadn’t realized that it would be a group ride, with the only person I knew peeling off early. Perhaps this is surprising, but I actually have never been on a proper group ride before,¹ and I wasn’t sure if I was feeling up to one. And third, they wanted to start at seven in the morning, whereas I was interested in sleeping in.

But despite not joining them for the ride, I decided to take some inspiration from their itinerary, and do another classic NYC cycling route up from the city to Bear Mountain. I was doubtful that I’d be able to make it all the way there and back, but I figured it’d be within my ability to at least ride there and then take the Metro-North (a local commuter train line) back.

Overall, I think the ride was a rousing success, if I do say so myself. It was fun getting to escape the city and explore some parts of the Hudson Valley that I’d never seen before, and it was reminiscent of the kind of cycling adventures around Pittsburgh that I used to have back in college. Below are some notes on the trip and a couple of pictures. I usually try not to stop for pictures too often on bike rides, because it just slows things down too much, but this time I really couldn’t resist.

Being on my own, I started at a leisurely 1:30 pm, which frankly is already an early start to a Saturday if you ask me. The first roughly twenty miles of the ride were not all that interesting, following the well-trodden route from midtown to the 9W market. I decided to stick to 9W itself this time rather than follow Henry Hudson Drive down by the river in order to save time; the really interesting parts of the day were still well ahead of me.

I didn’t linger for long at the market, only stopping to eat a couple of strips of dried mango and a handful of granola. Continuing on, I passed through some of the lovely little towns along the Hudson; I especially enjoyed this one street of houses in Piermont lined up along a creek, as well as the little downtown area.² Every time I pass through these small towns, it makes me wonder why I bother living in the city.³

Soon enough, I made it to Nyack, which marked the furthest point that I’d previously cycled up from the city. During earlier rides, I had crossed the Tappan Zee Bridge here to ride back down to the city, but today my route would take me further up along the Hudson. I was quite excited for this, because I always love riding new roads. By default, I had intended to just take 9W up, but Google Maps actually suggested that I take a multi-use trail by the river instead. I was a bit skeptical of this route at first, but I checked the pictures on Google Maps and it looked navigable on a road bike. So I figured: why not take the scenic route?

I’m quite glad that I did, because the trail was very nice, and certainly more scenic than the highway would have been. A couple of sections were a tiny bit uncomfortable on a road bike,⁴ but I managed to make it through just fine. There was a lot of pedestrian traffic on the first mile or so from Nyack, but it dropped off precipitously as I went north. Eventually, after a few miles of pleasant riding, I made it to the next town of Haverstraw, where I stopped to pick up a Twix bar (the best kind of candy bar) from a gas station before continuing on northward. I mostly tried to follow the green signs for New York State Bicycle Route 9 for this section, but I sometimes got a bit lost and had to rely on Google Maps.

The last major stop of the day was Cove Deli, where I rested for a bit and ate some more snacks. The ride on from here was on some mix of route 202 and a paved trail running parallel to the highway. While on the trail, I passed by a historical marker claiming that this was the site where Benedict Arnold plotted to betray the Continental Army, which I guess makes sense given that West Point is nearby. Unfortunately, I do not have a picture, because at the time I deemed the sign insufficiently interesting to stop and photograph.

Finally, I arrived at the actual objective for the day, namely Bear Mountain itself! Here, I was faced with a bit of a dilemma: it was at this point already 6 pm, which was a bit problematic because I wanted to get to the train station at Manitou before sunset at around 7:30 pm. It wouldn’t be terrible to ride in the dark (I had brought bike lights, of course), but I would have preferred to avoid it if possible. This left me unsure if I actually had time to summit Bear Mountain. After stopping to weigh my options and be indecisive, I eventually came to the conclusion that I had to do it; when would I next get a chance to climb Bear Mountain? And anyway, the Strava activity would look quite silly if I rode all the way here only to pass by the mountain itself.⁵

And so I began the climb. While certainly not the hardest mountain I’ve ever done on a bike, Bear Mountain is a proper climb, gaining 1,270 feet of elevation over 4.73 miles (according to the Strava segment), working out to a roughly 5% grade. This was the hardest climb that I’d done in a long time, and I could definitely feel how diminished my powers were from my peak cycling years in college.

After the grueling climb, I finally made it to the top and took some pictures of the Perkins Memorial Tower (an old fire tower that is now mostly a tourist attraction) and the attractive effect of the late-day sun low in the sky above the forest. But I didn’t have much time to enjoy the scenery, because I made a rather startling discovery: my plan for the day contained a near-fatal blunder! You see, I had assumed that I would be able to catch a train back to Grand Central from Manitou at any time of the day, because from my previous hikes in the Hudson Valley, I knew that the Metro-North runs hourly well into the night. What I had failed to realize was that Manitou specifically is a limited-service station, with only a handful of trains stopping each day. The last train scheduled to stop there for the day was at 7:33 pm, which gave me less than forty minutes to get there! Would I be able to make it in time?⁶

I was genuinely unsure if I’d make it, but I decided that I had to give it my best shot. I bombed it down the descent as fast as I safely could, and then crossed the Bear Mountain Bridge and rode up 9D. At this point, I had a sense that I was going to make it, because after getting off the mountain I was able to get cell service again, and Google Maps gave me an estimated ETA of exactly 7:33 pm—typically, an experienced cyclist should be able to beat the Google Maps ETA easily, so I wasn’t too worried. But still, I didn’t have much time, so I definitely had to hustle a bit.

I ended up pulling into the station with six minutes to spare. The timing was actually quite perfect, especially since the sun began to set just about then. The Manitou station is quite tiny—basically a single shack with a platform just wide enough for a single train car—and it was kind of fun to wait for a train all alone at dusk at this quaint little station in the middle of nowhere. It almost felt like a scene in a movie.

Anyway, I took the train back to Grand Central, from which I rode back to my apartment on W 30th Street. This was quite an unpleasant ride for two reasons: first, it got kind of cold after the sun had set, and I was underdressed in my lightweight cycling jacket and shorts. And second, I had the great misfortune of passing by Madison Square Garden right as the Knicks game was ending, which meant that the area was quite crowded. What a strange contrast from the serenely peaceful and empty little station that I had just been in.