The Summer Classic: Brewster to New Hamburg

Update: An anonymous benefactor was kind enough to update the route (7/2013). The updated route can be found here.

When I mapped this route several years ago, I had almost no knowledge of the local roads north of Brewster. So I just used Ride With GPS to sort of randomly draw a course on what looked like back roads in Putnam and Dutchess. I had no idea it was going to become the all-time summer classic ride!

After I posted this ride on Flickr a few years ago (and well before I had a blog) I started getting very positive feedback about the route from complete strangers via e-mail and Flickr mail. So it is a truly happy accident.

Anyway—at least in my opinion—this is one of the best moderate-effort rides within easy reach of New York City. In fact, I enjoy this route so much that it is one of the few longer rides I repeat multiple times a year. It’s approximately eighty miles. Virtually no traffic, in fact for 90% or more of the ride it is perfectly safe to ride side by side. It alternates between perfect road surfaces and gravel. Big climbs, some on gravel, and long, long descents.

The route begins at Southeast Station, the last direct stop on the blue Metro North line, and only 2 to 3 minutes past the Brewster stop. Here, I showed my friend Tom the route and elevation profile. Tom only rides with us occasionally, and you can see from this picture how he felt about it.


The station is in a deep hole that you’ll have to climb out of. A nice warm up for the rest of the day. Note that there’s a diner with acceptable food at the top of the hill if you want to stop for breakfast before continuing.

After climbing out of the hole, you’ll take a right on Dykeman Road (Route 312). Be careful here, because it’s a busy road. Luckily, you’ll only be on it for about 1.5 miles before you take a turn onto Farm to Market Road to head into the hills.


You’ll continue to Route 164, take a quick left and then the first right at the pond onto Cornwall Hill Road/Country Road 292, which you’ll follow past Whaley Lake. At the north end of the lake, around mile 14, you’ll find an outdoor hotdog/burger stand, probably blasting the worst music you’ve ever heard at high volume. The people I ride with always want to stop there for second breakfast (yes, I ride with hobbits), but between the gristle burgers and the awful music, I wouldn’t recommend it. They open at 10 am, if you’re interested in trying it out regardless. The hot dogs are safe.

Continuing on, you’ll take a left on Route 55…and then the fun begins. Hynes Road is a nicely groomed gravel path the swoops through the countryside through a tunnel of trees.


You’ll continue on Clove Road/Country Road 9, and at mile 25.5, you’ll take a left for one of the nastiest climbs in Dutchess County…Brush Hill Road. It certainly doesn’t compare to climbing Slide Mountain or Platte Clove on the other side of the Hudson, but it is not easy. My memory of it may be warped by the fact that we tend to ride this route on the hottest summer days; also, now that I live in the mountains I’d guess that I’d no longer find Brush Hill terribly challenging.

From there, you’ll cross Camby Road onto Flint/Overlook Road into some nice, rolling terrain.


This is our traditional first rest stop, on Hoxie Road. Pictured here you see my Rene Herse, Guy’s very special Jonny Coast randonneur and a James’ Hampsten.


You’ll continue to a brief stretch on 343, and then turn onto the appropriately named Little Rest Road. Off in the distance is the mountain I live next to now.


You’ll cross Route 44 in Mabbettsville at mile 33. For some reason, my GPS tells me to take a right here. Don’t listen to it, just continue straight past the deli. You might stop for a refill here, but you don’t have long to go to get to the lunch spot.

Continuing on, you’ll follow this road through mile 41. It goes through a variety of name changes in this 8-mile span: County Road 66, North Mabbettsville Road, Ludlow Road, Shuman Road, and then, finally, Bengall-Amenia Road. I’m not sure why, but Dutchess is notorious for random road name changes. In any case, just keep following the road.

I didn’t take any pictures of Bangall-Amenia Road, for the simple reason that I was going too damn fast to whip out the camera. This picture was taken while stationary.


Now, listen carefully: Ignore your GPS for a moment and follow Bangall Amenia Road all the way to Hunns Lake Road. Take a left, and about 300 feet down the road you’ll see the Bangall Whaling Company. Lunch. We’ve been there a number of times now, so they are familiar with the clan of lycra. The first time we showed up, though, we got some odd looks. We made friends, and they ended up giving us a bottle of wine, which my friend Guy subsequently had to haul over another 40 miles of hills. Luckily, he had panniers that day! Check ahead before you plan on stopping for lunch, their hours seem to change seasonally. They should be open for lunch during the summer, though.

Return to Bangall Amenia, go up a short hill, and take a right onto Duell Road, and then another right onto North Anson Road at mile 42. This is where many miles of serious gravel begins.




Eventually, you’ll end up on Petit Road. At the crossing with Canoe Hill Road at mile 48.5, Pettit Road is often blocked; if I recall correctly the sign says something about “The Cary Foundation”. No worries if it is, though—just take a right on Canoe Hill Road and then the first left (Fowler Road, although it is unmarked) to rejoin the route.This leads to one of my all-time favorite cycling pictures, my good friend Guy doing some impromptu roadside repair work next to a pestilential swamp deep in the forests of Dutchess county.


Nearby, you’ll see signs for the Cary Institute of Ecosystem Studies. They own some beautiful land; if you have a chance take a right into the preserve, take a break, and enjoy some nature.

At mile 54, you’re in for a dirt-road climbing treat on Milewood Road. The first time I did this, it was in a stiff rain and I didn’t make it to the top because I couldn’t get enough traction. The fourth or fifth time I did this (and alone, this time), I lost traction and tipped slowly over onto the drive side of my bike, unknowingly knocking my derailleur out of adjustment. I got to the top of the hill, shifted into the biggest cog and bam! derailleur shifts into the spokes, bending the hanger and rendering my bike completely inoperable. Luckily, I was able to hitchhike to a train station. Don’t worry mom, it was with a nice older couple with their grandson in the back.

The remainder of the ride is a blast, because it has a distinct downward drift. Yes, there are a few stiff hills, but for the majority of the ride after mile 60 you’re going more down than up.


One final note: At mile 59.5, the route crosses the Taconic State Parkway. You heard that right: it doesn’t go under the Taconic State Parkway. It doesn’t go over the Taconic State Parkway. It crosses it at grade. Be very careful!

You’ll end in New Hamburg after a high-speed descent on Sheafe Road.

This is a fun ride, and nowhere near as challenging as riding on the other side of the Hudson in Ulster County. If you’re in reasonably good shape you should be able to make it, although there are a few genuinely difficult spots. It would be a good introduction to long-distance riding or a pleasant route to repeat a few times a year.

To get there: take Metro North to Southeast Station to start, return from New Hamburg. You’ll definitely need GPS for this, as many of the roads are unmarked. The route is here (and the updated route is here). Links to train schedules and general advice can be found on the About page.


Do yourself a favor: Skip 9W one weekend and try this!


8 thoughts on “The Summer Classic: Brewster to New Hamburg

  1. Eric D

    John, really excellent blog. Can’t thank you enough for taking the time to put all of this great info together. I’ve been looking for resources on routes in the Catskills (where I was born and grew up) that are still accessible from NYC and your blog is just the ticket.

    With regard to this Brewster to New Hamburg ride, any reason you can’t do this route (or any of your routes for that matter) on a dry winter day on 23 or 25c tires?

    1. John Ferguson Post author

      Thank you! I ride all my routes on a regular road bike with 25 mm tubulars at 80 psi, so yes, it is completely feasible. These definitely aren’t mountain bike trails. Keep in mind that I weigh 145 lbs, so your mileage may differ. The one place where you have to watch out is on Cutter Road, which joins Lundy Road with Route 55. I use that road a lot on my routes. If you are heavier and on narrow tires, you will have to hike-a-bike for about a quarter mile.

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  4. Evan

    Did this yesterday and it is an amazing ride, one of my favorites now. We extended it down through Beacon and ended at the Newburgh brewery which was nice. Leaves were already changing which made it even more beautiful. Bengall Whaling Company seems to be permanently closed now, but there was a nice spot right at the bottom of Bengall Amenia road called Red Devon. Thanks for an amazing route.

  5. Alex

    Did this ride on the 5th coming from the city. Enjoyed it thoroughly. Scenic and authentically rural. Lots of fresh new pavement, so probably has a bit of a different feel than when you first posted it. Thanks for your posts. Glad to see that there are other cyclists passionate about dirt and hills. Planning to do a ride on the 25th or 26th from Cold Spring to Manitou around Fahnestock via East Mountain Road, Sunken Mine Road and Old Albany Post Road. Looking forward to more dirt climbing!

  6. David

    Thank you so much for compiling this list! I’ve been buying every outdated ride guide book for the region I could find and none of them have any gravel road sections. I’ve been searching for this site! I live in Brooklyn and I just put together a 650b bike I’m excited to put some miles on. I can’t wait to get started!


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