Autumn on the Empire State Trail
It’s mid-November as I write this, approaching the tail-end of autumn in the Northeast. The days are getting colder, and the nights are coming earlier, so the window of time to get any upstate rides in before the impending snows close the trails is waning.
I had ridden the North and South County Trails till I was blue in the face, and I was saving a trip to the New Croton Dam via the OCA Trail for when the fat tire ebike I ordered finally arrives after spending three months on a boat in the Pacific. I had also ridden from Brooklyn to Brewster last summer for a particularly punishing 70-odd miles. So, this time I was looking for something rural but easy.
The Empire State Trail, a network of trails really that runs from NYC to Canada, and from Albany to Lake Erie, has an off-road stretch from Brewster to Poughkeepsie, and knowing that both towns are on the Metro-North, I looked into what it would take to ride from end to end: 33 miles total distance, relatively flat, totally doable on a Saturday! I decided to ride the train up to Poughkeepsie and then to ride southeast from there, starting from the Walkway-Over-the-Hudson, leading onto the Dutchess Rail Trail, then taking the Maybrook Rail Trail at Hopewell Junction to Brewster.
The last time I was in Poughkeepsie touring the Walkway-Over-the-Hudson was for a pre-pandemic day trip to the Vanderbilt Mansion, so it was a little bittersweet to revisit. Offering panoramic views of the river for miles, the park was built atop a reclaimed rail bridge that was ruined by a fire in 1974. That same fire shuttered the entire rail line, actually, leading to the trail being created commissioned and finished in the past decade.
The entry to the park was a short stroll from the station, with clear signage pointing the way, and the entrance to the trail of course is directly adjacent, with sparkling clean facilities and spots for a snack in between.
Poughkeepsie is… Poughkeepsie. Oddly enough the colors were best riding out of town, but the scenery for the first few miles was to be desired — the trail mostly ran behind a bunch of scrap yards and used auto lots. Nevertheless, I preemptively downloaded an “autumn jazz” Spotify playlist to play quietly on my bluetooth speaker while I rode, nothing too offensive or jarring to peds, and some less than stellar scenery aside, with the overcast sky and the crisp air tinged with the warm smell of wood smoke (or was that diesel exhaust?), the autumn vibes were strong. This is why biking is my favorite hobby.
I’m a sucker for mysterious relics of old infrastructure, and there are a few hints of the trail’s past life as a railroad still remaining, like this crossing signal.
A third of the way through, I passed through Hopewell Junction, which has a cute, old train station they converted into a museum (with bathrooms and vending machines for drinks and snacks, most importantly). It’s as good a place as any to take a little break, plus although I didn’t detour into town for lunch, there seemed to be plenty of spots for a bite to eat more satisfying than a Clif bar.
Unfortunately the museum was closed for the season.
The trail becomes the Maybrook Rail Trail from there, and it follows some actual disused train tracks for the rest of the way.
You’re still in “civilization” as the trail runs through the outer suburbs and over some highways, but the scenery gets progressively nicer as you go, the houses bigger and richer. Along the way, I passed what looked like a grand estate at first, but what turned out to be a country club. I didn’t take any pictures because, well, it’s just a fancy golf course, whatever. Upon examination of the trail route for this very write up, I learned that it was none other than the *rump National Golf Club.
Coincidentally maybe, not far afterward I eventually also passed a prison.
As you ride near Pawling into the mountains, the scenery becomes rather woodsy and wild, and fellow trail-goers become fewer and far between. In a few places the treeline gave way to the mountains in the distance, and farmland vistas. You even intersect with the Appalachian Trail, where you’ll meet some rushing rapids. This was probably my favorite stretch but do note the number of chances to “escape” the trail onto a street became rarer the farther I went (see below).. Onward to Brewster, coming down off the mountain you’ll pass some wetlands and swamps, where I didn’t see a soul for at least a mile or two. You could stop riding and just stand there and hear nothing but distant prop planes overhead, and the birds in the ponds.
At Brewster, the trail splits off, and you’ll have to ride a short bit through town streets to get to the train station. All told, this was not a difficult ride and something I would definitely try again, perhaps in the opposite direction next time.
TL;DR AKA Vital Statistics:
- My ride from the Walkway-Over-the-Hudson in Poughkeepsie to the Brewster Metro-North station ran about 39 miles, according to Strava. I totalled about 3 and a half hours, with a number of breaks for rest/photos/waterfall-adjacent contemplation.
- The Dutchess County and Maybrook Trailways are both impeccably maintained, wide, flat, and mostly paved, so any road bike will do the job. Eastbound there is a slight grade as you head into the mountains, making the trip a little more strenuous than I originally anticipated, but nothing bad at all.
- FYI there are sections, the last 10 miles going into Brewster for instance, that are very pretty, but kind of desolate — a lake to your right, a mountain to your left, and not a soul in sight ahead of or behind you. Meaning if you get a flat, a broken chain, or any other mechanical issue you aren’t prepared for, I hope you’re comfortable walking. It was getting dark by the time I made it this far, and I had no service on my phone, so the slight anxiety was creeping in. Definitely do not do what I did and bring some kit.
Like this bike-thru? Here’s one I wrote about the South County and Old Croton Aqueduct Trails from NYC to Tarrytown.
