44.6 mi / 9.9 mph / 1054 ft. climbing
Home: Ed’s WarmShowers Apartment

Contractors arrived on the morning of our departure, beginning a major renovation of Luke and Andrea’s House with perfect timing (for us at least!) We weren’t forced to camp in the backyard, and now on our next visit, we won’t have to kick Sidney out of her room.

We left their house early, but didn’t actually leave Chappaqua until noon, because we were waiting at the poorly-rated Walgreens to get some prescription refills (they actually took care of us well, with most of the delay coming from time-zone differences with our Washington health care provider). It’s one of those things that’s trivial for people with a home base, but a stressful chore for us.

I needed to continually remind myself that we were not actually repeating a ride from Chappaqua to New York City that we’d done two years ago. Because it certainly seemed like that’s what we must have done. After all, I had memories from then of traversing Manhattan, and loading our bikes onto a ferry at Wall Street and sailing to Sandy Hook, New Jersey.

But the proof of my implanted memory was that every part of the ride was brand new. Two years ago we had in fact scooted east into Connecticut from Chappaqua, tooled around New England for weeks, and only returned to kiss Manhattan by bouncing off it via a ferry in from Long Island (our Manhattan traversal had been on foot, on a day trip in from Chappaqua).

The Empire State Trail is the umbrella over the sequence of trails that comprised 33 miles of our day. The six miles of Westchester County road riding was relatively peaceful, with only one quarter-mile section where sidewalk riding was the better part of valor.

The trail was then a hidden wonder. Not that the view from inside was especially stunning (though it was certainly a pleasant green tunnel). Rather, it was impressive how well it hid the highly-populated, road-crossed region from our view. Well, there were a couple painful and awkward street crossings through towns, but mostly, the old railroad bridges kept us isolated from any knowledge of what was going on outside of our corridor.

The trail also kept us surprisingly isolated from other cyclists. Yes, it was a weekday around 1pm, but we still saw only a fraction of what I would expect on similar trails in Chicago (North Branch) or Seattle (Burke-Gilman). But then I realized that the near-unbikeable roads of Westchester County surely contribute to its underuse. Since you need to be a really confident (suicidal?) cyclist to ride your way from your house to the trail, almost no one will do that. So that leaves driving your bikes to a trailside parking lot, an action that requires far more intention and effort than just hopping on your bike and pedaling over. And then that just means there is less of a culture of cycling built among the area’s families (seeing zero kids on the trail was the big clue to the reason for its emptiness). The upshot is that there is this wonderful resource running through the county that is much more-valuable to long distance visitors passing through, than the county residents. Especially since it makes entry into the nation’s most-populous city almost effortless.

The end of the “suburban” section of the trail is hilarious in its audacity. The green forested tunnel turns to cut across a park, and then, WHAM, you’re in NEW YORK CITY. Literally on Broadway, with the “subway” roaring on the tracks elevated overhead, regularly dispensing streams of pedestrians to fill the sidewalks, to pop into a couple of the hundred storefront shops filling each block, and, at least in this part of The Bronx, the NYC classic of everyone dodging bags of garbage sitting out to ferment.

We dodged that garbage ourselves to bypass the traffic-clogged avenue, but got ahead of it to cross the bridge onto the island of Manhattan, at its extreme northwestern corner. That corner features some surprising elevation, so it was quite a climb up to the trail paralleling the Henry Hudson Parkway. I’ve always thought of Manhattan as a low-lying wisp of land turned Dutch-style productive, but here there is no danger of flooding by the adjacent Hudson River!

Bike paths continued down the west edge of the island, in various forms and conditions, but becoming steadily more crowded as we progressed south. When we reached 14th Street and needed to turn left off the bike path (to pick up some pants at Lululemon), it was a dangerous challenge. The steady stream of oncoming cyclists made it difficult to find a gap, and slowing/stopping in the middle of the lane (since there is no left turn lane!) risked triggering a pileup of all the cyclists behind us.

It certainly didn’t help to know that high-powered e-bike and scooter riders might come flying past us at any moment, hurtling at more than twice our speed (and ignoring the signs saying that electric bikes and scooters are barred from the path). Those guys are a real menace, and the ones wearing motorcycle helmets and full body armor communicate that they expect to crash into one of us, and expect to come out the winner.

It’s the highest density of cycling I’ve ever seen in the United States, and it reveals in retrospect that a magical age of urban cycling in this country may already be in the past: that era of the first decades of the 21st century, after cities had begun dedicating street space to bicycles, but before bicyclists had swarmed into those reserved spaces. In that age, you could actually navigate a dense urban core faster than gridlocked vehicle traffic, but now backups have come to the bike lanes too, and show that it wasn’t something inherent about bicycles that made travel so efficient, it was simply due to underutilization of the allocated space! In 2026 in a place like Manhattan, I’m sure there are already people who have turned away from cycling as a mode solely because there’s too much damn (other bike) traffic!

After the Lululemon stop, Rett had the good idea to get some cooling and energizing smoothies from a street-corner cart before we commenced our final phase. We had passed a cruise ship docked on the west side of Manhattan, but the Queen Mary 2 departs from the Brooklyn Cruise Terminal, and we intentionally had chosen a WarmShowers host near the terminal. So we went back to the west side path, continued south until Manhattan narrowed, made another treacherous left-hand turn off the path, and crossed toward the Brooklyn Bridge!

We’ve pedaled ourselves and all of our possessions through a lot of remarkable places in the world, and I don’t know if this ranks too highly, but “Rode Across the Brooklyn Bridge” just feels like something we should get a sticker for to include in our (imagined) sticker collection. There is a dedicated two-way bike path (with fairly-easy entry/exit), separate from the dedicated (and even more-crowded) dedicated pedestrian path. Unfortunately, there was no where to even pause on the bike path without creating a traffic jam (or crash), so we barely saw the bridge (100% of our focus needed to be on the cycling), but we still should get the sticker.

Brooklyn somehow felt a bit calmer, maybe because the cyclists are more evenly-distributed around the street grid. And then it was blessedly simple to get up to Ed’s 8th-floor apartment: his communication (and patience!) had been excellent, a doorman held the doors to let us in, we both squeezed into an elevator, and our day was done!

We got our warm showers, and then Ed, a Brooklynite for seven decades (is he those sole remaining native?!) was proud to show us to any place we could possibly want to eat within a short walk (we chose a Thai place). Our conversations mostly avoided the boring stuff about cycling, but I was fascinated to learn that not only was he one of the rare people who has an (imagined) sticker for Bikecentennial (riding his bike across the country in 1976, on what was to become Adventure Cycling’s TransAmerica route), he was one of the even rarer ones who was well-prepared and knew what he was getting into. In 2026 we still encounter people who are flabbergasted when they hear that we’re riding our bicycles across a single US state, so it’s hard to imagine how crazy the idea of riding across the entire country must have seemed to 99.9% of the US population 50 years ago. To Ed, it seems like the idea was nearly obvious, so even though he doesn’t see himself this way, we were spending the night with one of the true godfathers of US bike touring!