Biking the Empire State Trail - Schenectady - Albany - Hudson

The Quick Stats:

• Route: NYC → Schenectady (Train) | Schenectady → Albany (Bike) | Albany → Hudson (Train) | Hudson → Albany (Bike) | Albany → NYC (Train)
• Distance: ~56 total biking miles over 2 days
• Rig: Second-hand road bike on 25mm tires with frame bags
• Vibe: Beginner-ish, scenic, event-filled, emotionally reflective

I’m writing this to share a fun, beginner-friendly multi-day bike ride and, hopefully, to inspire you to take a similar adventure without repeating my mistakes. This is a story about overcoming challenges and growing as a human.

Looking Forward, Not at the Wakes

I had set my sights on the Empire State Trail after hearing my running friend Amy talk about biking from Buffalo to Albany as part of a multi-day guided tour. But what finally made me pull the trigger was grabbing dinner with my friend Funmi on a Wednesday evening—shortly after stepping away from my last role to take a brief breather—and hearing about her 7-day ride from The Bronx to Montréal.

Part of my motivation was symbolic: I wanted to let go of the job I’d just left. It was a role I enjoyed a lot, but it ultimately wasn’t the right fit.

On the train heading north, I initially sat alone. As we moved along, I realized I really wanted a clear view of the Hudson River. There were no empty rows on the river side of the train, but there was an open seat with a view next to a woman. I moved over, hoping she wouldn’t resent having a person next to her. I forget how we started talking, but somehow we did. She was on her way back home from NYC. She explained to me how she had owned a business in NYC for decades that she had to close during COVID-19. She told me the story of how she shut it down and got jobs for all of her employees by reaching out to other leaders in the industry. I told her she was a good business owner.

She gave me a piece of advice that stuck with me for the rest of the ride:

Look forward, not at the wakes. Think about what it is you want more of in your life.

As I started pedaling in Schenectady, feeling light sprinkles of rain and the Erie Canal on my left, I kept trying to answer that question.

The ride along the Mohawk River was the one I had dreamed of.

Lesson #1: Respect the Warning Signs

About 15 miles in, I noticed a strange, bumpy resistance in my rear brake lever whenever I pulled it. I kept going.

Then came a steep hill. I love the thrill of going fast downhill. At the top, a sign read: “WARNING – WALK BIKE DOWN HILL.”
I thought: “That’s boring.” The hill was steep, but there was no one around, risk was relatively low, so I kept rolling, just a little slower.

Ten seconds later, a second sign said the exact same thing. I thought: “Okay, it’s a warning, not a mandate.” I squeezed the brakes a little more to moderate my speed—and immediately heard a SNAP.

The rear brake lever went totally slack. The end of the cable had popped out of the socket. No rear brake at all. I’d ignored two signs and a bumpy lever, and that was on me.

I stopped and assessed the situation. I didn’t want to cancel the trip, but completing a multi-day ride through hilly terrain with only a front brake felt dangerous. I needed a bike shop, even if it meant a detour. I took some shelter on the path and called around and found Freewheel Bike Shop.

Left Behind, Kept Rolling

When I arrived, a mechanic named Maira put my bike on the stand and let me watch her troubleshoot. She quickly figured out the culprit: the way I had strapped my front and middle frame bags was putting extra tension on the brake cables, causing them to bind and snap under pressure.

As she replaced the casing on both brake lines and the rear brake cable, she noticed the “Feminist Killjoy” sticker on my frame and asked about the bike’s history.

It wasn’t actually my bike. Years ago, a friend left the bike in my care, left the country, and stopped all communication. Before that, the previous owner—a former bike messenger—had gotten it second-hand, fixed it up, and gifted it to my friend.

I asked Maira: “Does taking care of a bike for years make it yours?”
She thought for a second and said it was complicated. She shared that a friend had sold her gear years ago for dirt cheap. Before buying it, she asked them if they were sure they wanted to sell it, and they said yes, explaining they were done with bikes. She wondered about their mental health, so she checked in with them, and they said they were fine, and just wanted a change, so she agreed to the exchange.

Years later, the friend changed their mind, decided to take up biking again and asked for it back. She explained to the friend that she had come to depend on it and didn’t want to give it up.

(For what it’s worth, everyone I ask has a different take. I’m always curious how people define ownership. Two people told me it’s definitely mine now—one even suggested I repaint it! A dear friend said it’s a no-brainer to return it if the friend ever reappeared. Personally, I still love that friend, and if they asked for the bike back I would hesitate and explain the upgrades I put into it, but I would probably give it back.)

Maira replaced both cable casings in 20 minutes, gave me her phone number in case I ran into trouble further down the trail, and offered some solid parting advice:

Go slower down hills in this damp weather—the trail surface can be unpredictable. And don’t doubt yourself during this career transition.

I left and continued pedaling toward Albany.

Lesson #2: Verify AI and Crowd-Sourced Data

My original itinerary was Schenectady → Albany → Hudson all in Day 1. I had relied on a quick Google AI search overview for distances, which made it look totally doable.

However, when I mapped the actual route in the Ride with GPS app, I discovered two alarming things:

1. The distance was actually closer to 60 miles for the day—about 15 miles longer than the summary suggested.
2. The app claimed 30% of the Albany-to-Hudson stretch was unpaved.

Riding on narrow 25mm road tires in light rain over damp, crushed sandstone was not something I wanted to risk for 11+ unpaved miles. So I pivoted: I decided to bike Schenectady to Albany, take the train down to Hudson for my hotel, and then bike back north from Hudson to Albany the following day.

(Spoiler: The app lied about that unpaved section, too. Out of the entire ride from Hudson to Albany, less than a quarter-mile was actually unpaved. The rest was smooth, paved.)

An Excuse to Sleep In

Because of the brake detour, I was rushing to make my 4:30 PM train from Albany to Hudson. I made it, but a new problem emerged: my hotel in Hudson didn’t allow bikes inside.

I called customer support from the train. They suggested leaving it outside on the front porch or in the backyard. I knew I wouldn’t sleep worrying about it getting stolen. I messaged Funmi because she had previously stayed in Hudson with her bike and knew the vibe of the town. She suggested throwing a tarp over it in the yard, but the hotel had no tarps.

Finally, I called a local sporting goods store in Hudson, Steiners Sports, a few blocks away. The owner kindly agreed to store my bike inside overnight. The only catch? They didn’t open until 10:00 AM the next morning.

That “catch” gave me an excuse to sleep in and recover.

The next morning, after retrieving my bike, I set off from Hudson back to Albany. I hadn’t packed much food—just some macadamia nuts and two bags of trail mix. I couldn’t get the trail mix open, so I ate the macadamia nuts.

Despite the light rations, the Hudson-to-Albany ride was breathtaking.

The Finish Line & Reflection

I rolled into the Albany train station to catch my train back to NYC with 10 minutes to spare. I bought beverages and yogurt and headed to the train. As I got on the train, I looked down at my arms and legs: they were covered in tiny gnats. I was riding so fast—they had just splattered on contact.

Did I accomplish my goal of completely letting go of my last job and finding crystal-clear clarity for my next steps?

Honestly, I don’t know. Life is a continuous journey, and it can sometimes take time to find clarity. I wish I could offer a dramatic “hero’s journey” arc where I reached the end of the trail and experienced an instant epiphany.

Instead, I got something better: a genuine adventure. I dealt with mechanical issues, adjusted plans on the fly, met incredible people along the way, and realized I am fully capable of handling whatever the trail throws at me.

What’s Next:
I want to continue along the Empire State Trail, piece by piece. I’ll probably skip the Hudson-to-Poughkeepsie stretch (too much shared road traffic with cars), but I have my eyes set on Brewster to Poughkeepsie, followed by Brewster all the way down into Brooklyn!

If you’re reading this and thinking about planning a bike trip: do it.

Before you go, check out my tips for biking the Empire State Trail.