Round Hill via School Mountain Road (Fahnestock State Park)

Round Hill via School Mountain Road (Fahnestock State Park)

Hike Type: Lollipop Loop

Distance: 4.61 miles

Elevation: 712 feet

My Time: 1 hour, 39 minutes

Book Time: 2 hours, 39 minutes

Parking: Plenty roadside parking at School Mountain Trail trailhead.
Hiking Challenges: 52 Hike Challenge 2026, Downstate 28er

The Hike 

I was in New Jersey/PA for the weekend to celebrate my cousin's wedding and I wanted to find a stopping point on the way home to break up the drive. I could have done a Catskill High Peak, but I didn't want to go that far out of the way on a Sunday, and then I remembered the Downstate 28er list (which appears to be by the same folks who made the Taconic 12er!). I looked at the hikes that were furthest from Mom's house and landed on two in Fahnestock State Park. The plan was do to hike Round Hill and Candlewood Hill before launching myself back to Boston. I had a nice drive, a little over an hour long from our breakfast spot in Towaco to the School Mountain Road trailhead, which was a long dirt road with plenty of pull-offs and a parking lot (with a porta potty!) a bit further down. It was a humid, sunny 82 degrees when I arrived. I put on my new hiking clothes from Target (underwear that I feared was too short for my thighs, new 7" inseam shorts that I feared would be too soft and absorbent, and a new "active" shirt that I feared would be too heavy and absorbent. Starting off strong!

I started my hike on School Mountain Road, which was an old gated gravel road that was delightfully flat. I was planning to avoid bug spray for as long as possible, if that would be possible. I was excited to see that the trail markers were the Taconic Region ones, for no reason besides a little teehee. 

A minute or so into the hike, there was a kiosk with a map for the Hubbard Perkins Trail, which partly coincides with this and other trails in the park. There was a wonderful floral smell in this area. I soon caught up to a man and his off-leash dog at a sign that specifically detailed why it is important to leash your dogs... I passed him, gave a "how's it going," and got zero response. Yikes!

The School Mountain Road trail crossed over a couple lovely bridges and then I crossed paths with another duo. They were both friendly, and the one ahead shouted "oh shit John! Hurry! You can see a bass!" which made me giggle. The trail continued into the woods with a very easy gain, passing old stone walls and eventually crossing a larger bridge. Just after the bridge was the turn I would take for the blue-blazed Fahnestock Trail up to Round Hill!

Right around here, specifically at the 0.4 mile mark, 9 minutes into my hike, my camera battery died! I was incredibly displeased with this. I hate doing phone-photo hikes. I also just don't like being on my phone more than I need to on hikes, besides taking notes. And I only like taking notes becuase it helps me relive my hikes with more detail when I journal them, like this! Either way, I continued onto the Fahnestock Trail, turning sharply to follow the stream back toward the meadow and the bridges from before. There were a large number of dragonflies that had a teal/metallic thin body and black wings (a very specific google search looks like they were ebony jewelwings, also known as black winged damselflies).

The bugs started to increase, but I just kept my pace up, really avoiding the Deet. The trail stayed flat for a bit, eventually turning away from the water at another old stone wall. After the turn, the trail began to easily rise around the base of Round Hill.

As the vegetation increased, I eventually gave up and coated myself in bug spray, and it was a good thing I did! The trail became pretty overgrown and generally unpleasant to hike through. After rounding the corner, the trail began to start a moderate climb up the spine of the hill, switchbacking here and there with an overwhelming floral smell (which would have been lovely any other day, but not in the humid huff-and-puff). 

I hiked over what I'm pretty sure was a wild cockroach (?) as I was actively dripping pollen-soaked sweat. The baby blubes were taking shape, at least! There was a slightly overgrown view towards Bear Mountain, which was nice to see! I also passed a neat orchid-looking flower (a Goat's Rue, thank's Seek!). As the grassy climb continued, I found myself feeling less excited about getting in the car to get another hike in, so maybe I'll just extend this one? We'll see.

After rounding the shoulder of the hill, the trail worked through a pretty open-ish area that was ridiculously grassly (a la Harriman State Park's Long Path). I had to bug spray my upper thighs becuase the grass was so high. There were some tree views to the left as the trail crossed another old stone wall, and then I had to fight my way through a few thickets of raspberries (or blackberries, or wineberries... either way, thorns!). The grass got so thick at points that I couldn't even see my feet. I was not emotionally prepped for this hike.

I was quickly losing steam to extend the hike along the ridge, especially if this grass kept up. Naturally, after I had that thought, I crossed another stone wall and the grass became waist high. The trail slightly descended before the final climb up. I wrote: "I rarely actively hate a hike but this is really trying for it."

There was a short steep climb before hitting some more grass. Thankfully, the trail flattened at some blueberry bushes before turning for the final push. There were some obstructed views before a wonderful view, where I encountered my first person in a while, going in the opposite direction. 

The Fahnestock Trail rounded the height of land. I took a spur/herd path to the true summit, which was marked by a fire ring and a makeshift cairn. Back on the main trail, I noticed a view out to a nearby hill with a massive observation tower-looking thing. There was a WONDERFUL breeze here as I entered more and more grasslands. There were at least nice pink flowers (carolina roses, thank you, Seek!). 

The trail descended into a low point and then rose just a few feet to the junction with the green-blazed Round Hill Bypass, which I HAPPILY took. At this point, I was pretty sure I was just going to do this hike as-planned and call it a day. I was NOT in the mood and I was already overheated - I'm not ready for full summer. 

This trail was MUCH more enjoyable. It easily descended with rocky footing into a fern-filled wonderland, and I could see my feet the whole time! Further down, I crossed a stream with an adorable frog swimming about and then hiked over another stone wall.

The trail then entered a really pretty open forest with stone walls in every which direction and a vast carpet of green undergrowth (only a few inches tall, which was so much nicer than the multi-foot tall grasses from before. I could tell this used to be farmland clearly, but curious how long ago? The park was opened about 100 years ago. I was missing my camera - it was so pretty!

The trail then turned and rose above a mossy stream that would be absolutely stunning after a rainfall. There was a parent and child playing in the water. The Round Mountain Bypass trail terminated just a couple minutes later at another nice bridge!

The bridge was designed by the West Point Cadets Civil Engineering Class of 2021. I thought about adding a loop over East Mountain, but the trail looked similarly horribly grassy - no thanks! I was back on School Mountain Road and happily hiking back to the car.

I crossed another bridge, this time designed by the West Point Cadets Civil Engineering Class of 2020. I spooked a snake that I thankfully did not see and continued my romp along the beautiful road. I unfortunately was in a slightly negative headspace, so I was not able to fully enjoy the back end of this hike, but it really was lovely. There were seemingly endless stone walls throughout. 

The next bridge was a longer one with wooden steps to reach it, and it was also designed by the West Point Cadets Civil Engineering, this time the Class of 2019. I passed another sightless snake and enjoyed the tall trees lining this trail. After a bit of walking, I officially closed the lollipop and hiked over the final three bridges (I forgot to check if the design pattern continued, but the styles of the bridges sure did match!).

I soon made it back to my car and started to wipe the sweat (and pollen) off and change my clothes. Comically, I realized my backpack had been open the whole time! I did not have the energy in me to squeeze another possibly unpleasant hike in, so it was now time for a long drive back to Boston, naturally with a stop at Stewarts on the way!

Step-by-Step

- Start hike on School Mountain Road (white).

- At jct., turn sharply right onto Fahnestock Trail (blue).

- At jct., turn left onto Round Hill Bypass (green).

- At terminus, turn left onto School Mountain Road (white).

- Return to car.

Fahnestock State Park Map

Photo Album