The climb out of NYC is always longer than you expect, I biked around 3 hours before actually exiting the city. After exiting the city, the trail promptly dumps you along a protected path that passes through much of the small towns further north. I originally intended to make it all the way to Poughkeepsie, but a delayed start meant that I had to stop early in Red Mills.

One interesting thing is that the trail passes through a lot of private property, and at one point I accidentally took a turn to get onto a street using a driveway that ended up being private property, and got a prompt scolding from the property owner. America is weird, man.

Passing over a small bridge on the way. Can't remember if this was on the way to Red Mills or on the way to Albany.

Along the way I rode with some interesting people, including meeting a guy who runs a private equity fund that owns container ships, and another guy who was very curious about the logistics of the trip. I found it curious that, here I was doing this long, contemplative ride, yet I was riding with this fast-paced PE fund manager.

Day 2 continued pretty well, I climbed out of the Catskills mountains and blazed towards Albany. The weather was beautiful, not too hot, not too cold, and my bike performed wonderfully on the climb out.

Some views from climbing out of the mountains.

One thing that's interesting about the Empire State Trail is that it links together many smaller disparate trails, such as the Hudson River trail:

This trail takes you over briefly to the other side of the Hudson, and you have to double back before reaching Albany. It's quite beautiful too, some of these trails take you alongside old, abandoned railways:

The rail trail is completely separated from the main road as well, although you'll pass through a bunch of smaller NY towns, such as Germantown or Mechanicville. All of these towns seem to have these odd martyr posters too, curious reminiscent of Iraqi martyr posters:

Albany is where the Empire State Trail gets a little shitty. I knew I wanted to sprint to Ticonderoga, but the road wasn't fully flat yet, and the trail basically stopped being protected at this point, and I was riding along the highway for a large portion of it. The trail cuts onto Route 4, which is a terrible and frankly quite dangerous route between Compton and Whitehall. I opted to take the side road, but had to eat significantly more hills as well.

Riding along the highway, complete with farm equipment.

Shortly after I exited Albany, I passed through a series of canal locks, which were quite cool to see in person:

The trail also splits here too, with one going to Buffalo and another one going to Canada:

I met a few other bikers who had come from Buffalo to Albany as well, who were excited that there were fellow bikers on the trail. During midday, I stopped at the Fort Edward bike shop, who gave me some incredibly good advice about the trail conditions.

I got up early in the morning to take the ferry over to Vermont. The Vermont drivers are significantly nicer than the NY ones too, although there were plenty more unpaved roads.

Along the way I continually met people who were curious about where I was riding to and where I had ridden from, which was cool to see. Many expressed surprise that I had come "all the way from NYC", although to me at that point I was closer to Montreal.

There's plenty of places where a flat could've caused a really bad day though, as there's no signs of civilizations in large sections of the road.

I passed through many tiny Vermont towns that were founded before 1776, which was interesting to see. It made me think about how, in Iraq, I used to live next to Buratha Mosque, which is a 7th century Nestorian church. I’ve napped and drooled on bricks a millenia older than these towns. Seeing all these tiny Vermont towns made me consider how young America actually is, and what ramifications that has on its society.

I originally intended to stay in a hotel on the Grand Isles, but I couldn't find an opening, and had to settle for a hotel in Burlington. Learning to budget and roll with the punches was pretty helpful for this trip.

This day was by far the worst, although it was a pretty flat sprint to Montreal. I only passed through a single major town in Canada: St. Jean Richilieu, which seemed pretty unremarkable.

The Canadian border guard was a little confused about me showing up with a bicycle, although he let me through without a fuss. This was all highway-hugging riding too, no bike lanes to be found. I passed through the border checkpoint mid-morning, and promptly sped off to Montreal.

I was struck by how similar Quebec was to midwest America. With cornfields as far as the eye could see, Quebec was a lot more reminiscent of my days at UIUC than I was expecting. The drivers were definitely still nicer than NY drivers though.

Funnily, immediately after arriving in Montreal, I had to pass through the north end of Rue Ontario, and even late afternoon it was possible to see what a shitshow the north end of that street is. Montreal is an interesting city, it's American influenced, but definitely not American. Biking in, I was immediately struck with how it'd make a great city to buckle down for 2-3 months and get some serious work done.

Looking back, I'm quite happy I did this trip. It was challenging in a good way, but also very doable. It made me quite excited about doing more long-distance bike trips as well. I didn't plan too much gear, deciding to go on a credit-card tour the entire way, but my Disc Trucker performed admirably, with zero flats. The only problem I had was the chain sagging around day 4, but even with that it easily carried me all the way to Montreal. There's something to be said about being lost in the repetition, where 8-10 hours of riding a day gets you plenty of time for your brain to start wandering into weird places. I spent most of it doing reflections on my time in Iraq and Uruguay, and trying to figure out what I want to do in my 30s. The experience was much better than I had expected when I first planned it, I didn't really have any real expectations about it, but it was a great way to clear my head.