Mountain Climbing is Best Accomplished in Winter: The Shawangunk Ridge via Mountain Rest Road and Vista Maria

Warning: This ride involves ice, freezing mist, massive climbs, and fervent prayers to St Milhaus the Retainer.

On Saturday, my friend Doug was kind enough to come from Woodstock to start an intermediate-distance ride from my place in Olivebridge, New York. The weatherman reported that it was supposed to be 50 degrees and sunny.

He lied.

My girlfriend was in Los Angeles for meetings with agents, which meant the dogs were going to be home alone all day. So I got up at ass o’clock (that’s 6:00 am) to walk the dogs and make them do their business before I left. Unfortunately, my Rhodesian Ridgeback, Pandora, decided that she would pick that time to be a princess and wouldn’t go in the snow, so I had no choice but to leave her, hoping she could hold it.


So it was at ass o’clock thirty (that’s 7:30 am) that we set out from my place in a cold, misty rain at a temperature slightly below freezing.  Yes, that’s me on my winter cross bike, submitted as proof that I’m not just driving around taking pictures.


In case it’s not completely obvious, this photo was taken by Doug.

We initially proceeded west onto a gravel road. Bad idea. The road was covered in ice, and not 50 yards in, Doug took a fall. Of course this happened right after I said “be very careful!” Luckily, he was uninjured, or least uninjured enough to go back to my place, where we loaded a new route into our Garmins that did not involve gravel. Doug is clearly made of tougher stuff than me, because if I had fallen (and I came damn close) I would have stayed at home to nurse a broken chicken bone.

Setting out again in the opposite direction, we headed south to route 209 on roads that were lightly coated with snow and ice that was, at least, starting to melt.


There was a thick fog and a freezing mist that lent the ride a mysterious air, almost as if we were floating through the clouds.


We passed through this graveyard on Airport Road on our way to 209. Some of the graves here date back to the early 19th century. The second photo was taken by Doug.



After crossing route 209, we headed into our first big climb of the day, over the Shawangunk ridge via Mountain Rest Road. This climb has been immortalized in numerous reports, so I won’t belabor it here.

The funny thing, though, is that when I lived in New York and rode out here, I thought this was a tough climb. This was my first time going this way since moving to the Catskills, and I didn’t think it was that hard.

When you see the second bridge—shown here—you’re almost done.


The best part about this climb was the weather. It must have still been below freezing at altitude, because the cold mist clung to my sunglasses, where it froze, lending the climb a hallucinatory quality.



We continued through rolling country along the eastern edge of the Shawangunks to get to the next big climb over the ridge, Vista Maria into the town of Cragsmoor. Although you’re climbing through a lovely forest, there isn’t much vista to be had on the way up. Here’s a picture during a brief clearing.


Once you get to the top, you have the option of taking a right onto Sam’s Point Road. We didn’t bother, because we were essentially inside a cloud the whole way up, and figured that there wouldn’t be much to see.

By the time we started to descend, the sun had started to come out, burning away some of the fog.


The descent was fun, although we had to be extremely cautious because of the loose sand on the road. In the summer, this is probably a 50 mph descent. I hit 30 a few times on the way down, but I wasn’t willing to go much faster than that given the road conditions. Here’s where you get some great views, at least in the winter.


We descended into Ellenville, where we stopped for a late lunch. Then we took the quick route back via 209 to Kerhonksen, followed by a great climb back to my place. Because of the crash, we had gotten off to a very late start, and—frankly—I underestimated how long it would take us to climb Vista Maria. So we ended up riding the last bit in the dark.

This is when I started to pray to St Milhaus the Retainer, a minor deity that Doug invented just for me on our return trip. St Milhaus, you see, is responsible for keeping dogs from pooping on the floor when left home alone for too long. The girls are perfectly house trained, but—because we work from home—they don’t have practice going 8 or 10 hours without a trip outside.

I’m happy to report that St Milhaus answered my prayers.

Doug stopped in for a hot tea, and I had my usual ice-cold Coke. Yes, I’m an addict. I gave Doug a naproxen since he was sore from his fall earlier in the day. In the middle of the night, I awoke terrified that I had accidentally given him a long-expired sleeping pill–the bottles look almost identical. How do you explain to someone you’ve just met that you’ve accidentally given them the wrong drug?

After fumbling for my glasses, I dashed downstairs. Thankfully, the bottle was still on the table. Doug, if you’re reading this…it was naproxen!

I decided to compare Vista Maria to the other big climbs I’ve done in the area. Here are some metrics for comparison:

  • The average grade of Vista Maria is 7.0% over 3.3 miles. The maximum grade is 18.7%, and it’s a Cat 2 climb that peaks at 2062 feet
  • The average grade of Platte Clove is 7.4% over 2.9 miles, with a maximum grade of 18.6%, and it’s a Cat 2 climb that peaks at 2058 feet
  • The average grade of Peekamoose is only 3.9% over 4.1 miles, the maximum grade is 12.0%, and it’s a Cat 3 climb

So, at least by the numbers, Vista Maria is of similar difficulty to Platte Clove, and equally as entertaining.

Is this ride worth the trip? Definitely, although I couldn’t see anything for most of the ride due to the dense fog. It is certainly challenging, and I think it will be gorgeous during the summer in nicer weather. I look forward to repeating it.

Here’s the route we took, mapped from my house. At the end of the day, we rode 70.2 miles. I’m not sure where we went 5 miles off track.



I’ve also mapped the route from Poughkeepsie, for those of you who would like to try it from the train station. It is a quite reasonable 90-mile day ride.


As a note, this route includes a short segment to the north of Route 209. Why? Because 209 is no fun at all. Although there’s a wide shoulder, there is a lot of traffic. However, it is fast and flat, so if you’re tired from Vista Maria, you can skip this section and continue 10 or 11 miles on Route 209 to Old King’s Highway, just after Accord. There, you will take a right to continue the route. I’m also told by my friend John–who has lived out here much longer than me–that Berme Road, which lies just to the south of 209, is a good option here as well.


5 thoughts on “Mountain Climbing is Best Accomplished in Winter: The Shawangunk Ridge via Mountain Rest Road and Vista Maria

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