62.5 mi / 11.1 mph / 1990 ft. climbing
Home: Luke and Andrea’s House

In this part of New York heading south, the Empire State Trail is a fully-off-road, paved bike path. It also runs along former rail lines, so has uses much gentler grades than the roads that cross the still-significant hills on the east side of the Hudson Valley. Finding those gentle slopes was definitely a challenge for the railroad builders, so that means the route is longer than a more-direct road route, but the pros still outweigh that con, so we’re taking the trail!

We got another hearty buffet breakfast (waffles!) from our motel (the first time we’ve had that sort of American chain-motel breakfast in…a year?), and reasonably restored and refueled, set out and joined the trail less than a mile away. For the first several miles there was an odd surplus of benches. Like one (or two!) every 100 yards. Almost as if they got more “dedicate a bench” donations than they anticipated, and then had to buy extra benches to meet the “need”. But hey, if you’re a long-distance walker who has a condition that requires you to sit every 100 yards, this is the trail for you!

After Hopewell Junction, the “Duchess Rail Trail” segment of the Empire State Trail ended, and we continued on the “Maybrook Trailway”. There were big orange signs announcing that Duchess County doesn’t own the Maybrook Trailway, essentially just to say “don’t bitch to us if you’ve got an issue over the next 7 miles!” Well, the Maybrook Trailway was slightly less kempt (brush growing closer to the trail), (abandoned) tracks still ran parallel to the asphalt, and the benches dropped to nearly nothing, but it was still totally fine.

That’s when we attacked our big 400-foot climb of the day, one so gradual that RideWithGPS didn’t even recognize it as a “climb”, despite it looking like a massive hill in its elevation profile (our legs agreed with RideWithGPS’s analysis). Partway up we passed a NY State Police K-9 training center with an incredible amount of security surrounding it, as if they were breeding some kind of cyborg dogs in there and they don’t want word to leak. Soon after, we passed the Green Haven Correctional Facility, and that’s when I put 2-and-2 together: they must be using the prisoners as expendable training targets for their attack dogs, and that’s the cruel-and-unusual story they don’t want to leak out!

At the top of the climb we finally crossed the Appalachian Trail; I had been wondering how we hadn’t crossed it already in the Catskills or somewhere else, and looking at the route later showed that I wasn’t wrong to be expecting it sooner; the trail runs unusually close to the Atlantic Ocean here, both north and south of here it runs much more inland. It was the third time we’ve crossed it together on our bikes (Maine 2016, New Hampshire 2022, New York 2024), all west-to-east. Unlike that first time, we’ve talked with enough through-hikers that it isn’t the aspirational draw to us that it once was.

34 miles in we stopped for sandwiches from a deli in Brewster. This was a decision-point, and at a hillside picnic table we decided to stay on the trail rather than switching to roads. It would add at least five miles, but the mental ease of the trail that we had experienced so far (not needing to worry about vehicles, directions, or steep climbs) made it feel like the longer route would still require less energy. A short on-road section to get to the next bit of trail quickly confirmed our decision as correct!

Some raindrops began falling and threatened the ease of our ride, but an unexpected benefit of the trail appeared with perfect time: an underpass tunnel in which we could wait for the cell to pass. Several other trail users waited with us, including a curious guy who was kind enough to deliver our first example of a true New York City accent. He noted that one downside of the tunnel-shelter is that it floods, but while the rain was definitely heavy, the five minutes before it cleared out weren’t enough to swamp us.

At around mile 58 we finally needed to leave the trail and do the last four miles on the roads. I thought some energy would be really useful at this point, and thankfully Google revealed that there was a pizza place half-a-block down that magically sold drinks and ice-cream bars!

The curvy, narrow, and busy roads were just as terrible as I thought they would be, so it’s good we had the boost. We crossed the (active) rail line that meant we were finally in Chappaqua, and as we climbed the steep hill towards the towering Reader’s Digest building, a car turning right with us simply couldn’t wait, and came within a couple inches of Rett’s handlebars. As angry-scared as she was, she kept powering up the hill!

We went within half-a-block of the Clintons’ house (“say hi to Hillary for me!” was what several people had said when we told them we were heading for Chappaqua), but we didn’t stop to say hello because we’d been reminded that they were at the Democratic National Convention in Chicago.

One final steep subdivision hill and then we were at the home of Family Unit #3 of the summer, this one the most unique: Rett’s brother Luke, his wife Andrea, and their two kids. We know much less about who they are (we’ve never even met 5-year-old Robin!) than our parents in Units #1 and #2, so we were very much looking forward to remedying that. And for a break! Despite realizing that our “record setting” over the last week was not a desirable goal, today we once again nearly set a record, with our 62.5 mile distance slotting into 5th place across ~400 days of riding. Whoops!