Hike Type: T
Distance: 7.12 miles
Elevation: 2,096 feet
My Time: 3 hours, 16 minutes (3 hours, 8 minutes moving)
Book Time: 4 hours, 36 minutes
Parking: Limited roadside parking before the snowplow turnaround at the end of CR-3.
Hiking Challenges: Catskill 3500; 52 Hike Challenge 2026; Operation Alaska Benchmark Challenge
The Hike
I had a lovely week+ down the shore on top of a great month down in New Jersey, but it was simply time to be home in Boston! I decided I'd hit a hike in the Catskills on the way back up, so my alarm went off at 5:00am, and I said goodbye to Mom and was on the road at 5:15am! I made it to the trailhead for Bearpen & Vly Mountains at 7:45am, which was a little confusing. The paved road ended at an open gate on a gravel road that appeared to continue, and the end of pavement was clearly posted "no parking." I ended up parking on a pull-off alongside a meadow just before the turn around. The drive in along CR-3 was beautiful, and a guy in a golf cart drove up the road and turned around at the snowplow turnaround - I was sure I was going to get yelled at.
It was a STUNNING 59 degrees out as I got suited up. I was still confused about the parking situation, but recent trail reports make it seem fine? It was also a Monday, so I was not overly worried. I realized as I was getting started this was my first "bushwhack" hike of the Catskills, but by my understanding there would be a trail the whole time.
[8:00am - Start of Hike]
My hike started on the continuation of CR-3 along a gravelly road with snowmobile signage and lots of loose dirt. The road was lined in ferns and posted signs. The road began to climb more moderately and I could make out Vly's outline through the trees. There was some medium-large mammal running through the woods, and I was simply not enjoying the schlep up this road! The only redeeming quality was that due to it's width, there were no spider webs (I was still having post-traumatic stress from Redington).
This road crossed with another old road at 0.45 miles and then another at 0.6, slogging upward. The woods were pretty, at least! The road leveled out near the height of land in a notch of sorts. The gravel turned to cobblestones, and I slowly approached a spooky black cabin that I was not interested in learning more about...
[8:21am - Vly Herd Path]
From the spooky cabin, I passed a bunch of signage for snowmobile routes and NY State Land, and I turned left to follow what I believe is the state land line, which was marked with blue blazes and a very clear herd path.
I immediately caught a web to the face. I almost brought my poles with me, but even if I had, I couldn't have a repeat of my Redington situation. The trail nicely meandered through the notch before making a rockier and steeper climb. There were a few criss-crossing paths, but I kept to just the blue markings and it was fine.
I hiked past a nice, mossy jumble of rocks that would be slippery if I wasn't thinking, but with 1% brain, it was no problem. A steep stretch leveled out in a beautiful area full of birds and a light breeze. My legs were definitely feeling they haven't climbed a mountain in a while! I was glad I picked a smaller Catskill hike.
The next steep push was full of roots that I pulled myself up with, and the following flat stretch had a bit of obscuring undergrowth. I was catching plenty of spiderwebs, but thankfully only on the lower 2/3 of my body. I passed a muddy stretch before the trail tried and began to climb again.
This third climb was one of steep dirt that had my calves feeling like they were about to hop. I enjoyed a neat little bridge-tunnel situation and looking behind, I could just make out Bearpen through the trees. The path began to round the shoulder as the sun was shining on the trail. This climb kicked my butt, which I'm sure has nothing to do with a poor diet and minimal exercise over the past five weeks...
[8:53am - Vly Mountain Summit]
The summit had a small clearing and a bright orange canister on a tree! I noticed a herd path on the right as I approached the summit, so I followed it in hopes of a possible view (or a disc that I saw online) - nothing! Back at the summit, turning left and walking a few more feet brought me to a disc - yay! No views, but that's okay. I took my photos and continued my journey.
[9:00am - Vly Herd Path]
Naturally, I slipped almost immediately as the trail steepened. I did it again near the rock bridge-tunnel. Besides that, I was cruising! There were occasional old yellow blazes in addition to the blue ones. The skies overhead were getting hazy - I think it was wildfire smoke again. The lower flat spot had a full gazillion birds again, and I found myself hiking with t-rex arms to avoid brushing up on some plants.
[9:22am - Hunter's Cabin/Snowmobile Trail]
Back in the notch, I heard some dirt bike/machinery in the distance. I quickly hiked past the spooky cabin and made sure I was following the correct path (thank you, AllTrails). I was looking forward to the assumedly easier hike up Bearpen. I noticed the cabin had a sign that read "NOT a gun free zone" with some targets about... don't like that!
The road was posted as "snowmobiles only," but I took that as foot traffic is fine, too. There was an old stove in the woods. The road split and I turned to follow the left branch, which had some more running water on it than I wanted. There was an occasional nice floral scent and flowers in the sunnier areas. A hill was signed as "steep," which I didn't care for, but thankfully it landed at a walking break.
The road was very pretty and besides that steep part, quite easy. The road split again, with the road going straight but a STEEP connector turning left. The straight route led to a gentle switchback, and that was the route I HAPPILY took. This hike was not overly strenuous, but I was SWEATY! I hit the switchback, climbed to the top of that connector trail, and then almost missed my turn into the woods.
[9:40am - Narrower Snowmobile Trail]
This path was blazed as a snowmobile trail, but it was a narrow footpath? Maybe it looks much different in the winter? I admittedly know very little about snowmobiling. The woods were beautiful! The trees were open with low undergrowth. I was back to hiking through plenty of webs, which is just my state of being at this point. The trail climbed easily to moderately throughout with one mud pit I had to carefully dance around. The sunnier spots had some overgrowth, but overall it was in great shape! It was a little more grown in at the very end.
[9:55am - Main Snowmobile Trail]
I turned right back onto the main snowmobile trail. The air was beginning to smell like wildfire smoke, but I was simply delighted to be back out of the land of spiderwebs. There were a few mud pits to contend with full of dark-red mud and some frogs. I was back to cruising! There were signs for "no motorized vehicles" near the top, but there were definitely recent tire tracks.
[10:05am - Bearpen Mountain Summit Area]
I labled this as "summit area," because the whole top is long plateau with an unclear high point. I passed an old tractor-type machine in the woods on the right with fire pit materials on the left, and then the trail opened up to a hazy viewpoint with a fire ring.
I continued along on the path, passing a blue disc and a really cool gangly tree-lined path. The AllTrails track went a bit further down, so I did too. I passed another motor-type thing and a better view to the right of the trail - yay! It was super hazy out now, but it was nice to see something besides woods! Another viewpoint towards a ski area was on the other side of the path.
This was my turn around point, as it looked like the path I was following either ended here or plummeted straight down, and either way, it looked wildly untraveled. I found myself putting some puzzle pieces together - the views looked like ski cuts, the motors could have been rope tows... I had cell service so I did a quick google and this WAS an old ski mountain! The path I was on was the old auto road to the summit. Information from Wikipedia:
"The mountain was host to a ski area in the late 1950s and 1960s, originally called Princeton Ski Bowl. Taking advantage of the mountain ridge's northeast exposure and high snowfall, the ski area operated until a land dispute forced its closure. Skiing at Bearpen was an "upside-down" affair, as skiers had to access the summit via a rough auto road. Remains of the lodge and early rope tow ski lifts are still visible in the forest around the mountain top. The mountain is still a popular location for backcountry skiing. From the summit to the valley below skiers can tally around 2100 vertical feet of glades and backcountry trails."
On my hike out, I noticed a herd path on the right after all of the ski area stuff... I rolled my eyes and then shoved my way through plents and webs to what AllTrails calls the true summit. I loudly said FINE. It led to a clearing 6-7 feet in diameter, no sign, but there was a rock in a tree? It was less than a minute in and less than a minute out, so I guess worst case I wasted two minutes and best case I hit the real summit?
[10:24am - Main Snowmobile Trail]
[10:32am - Narrower Snowmobile Trail]
Back on the main snowmobile trail, I got a picture of a frog and was feeling grateful that I hit Vly first. I followed the super narrow snowmobile trail, almost slipping and falling just before reentering the main trail, but I caught myself again! That's three slips and zero falls! I was feeling HUNGRY and needing to change my Nalgene, but I knew it was an easy walk down to the car, so I suffered in peace. I caught a tree view to Vly from the steep part of the main snowmobile trail and thought about how this would be a lovely snowshoe.
[10:57am - Hunter's Cabin]
I was delighted to be back in the notch and scurry past the spooky cabin. I took some photos of some irregularly shaped yellow flowers and managed to get stung by nettles! It hurt at first, and then itched like hell for the rest of my hike. The whole final descent featured a delightful breeze while the loose rocks were driving me insane. The road flattened near the end, passed a meadow that I simply did not remember, and soon enough I was back!
[11:15am - End of Hike]
Back at my car, two cars pulled up right as I was changing. One stopped at the end of the pavement and one backed up to park behind me. The other person left their car and joined the one at the end of the pavement, and then they drove maybe 30 feet up the gravel road before stopping? When I started driving, I turned around at the snowplow turnaround, they got moving, and so did I.
The GPS saying I had FOUR hours to drive to get home hurt, but I accepted my fate and got to it!
Step-by-Step
- Park at the end of CR-3 before the snowplow turnaround.
- Start hike on snowmobile trail ahead.
- At hunter's cabin, turn right onto herd path, following the blue-blazed Catskill Park boundary.
- At summit of Vly Mountain, turn around.
- At snowmobile trail, turn left, backtracking, and then immediately right onto another snowmobile trail.
- At split, turn left.
- At jct., continue straight to switchback.
- Just after next jct., turn right into woods (this is marked as a snowmobile trail, but feels more like an overgrown footpath).
- At terminus, turn right onto snowmobile trail.
- Explore the summit area, and then retrace steps back to the car.
