Whitestone Cliffs Trail

I Smell Hippies
Plymouth, 1.7 miles

March 31, 2009

wcf.jpgHaving just finished up the surprisingly excellent Hancock Brook Trail a couple miles to the southeast in Waterbury proper, I drove the 8 minutes over to Plymouth and the short Whitestone Cliffs Trail. This section of the Mattatuck State Forest is tucked into the little corner of Plymouth just north of the Waterbury line and east of the Thomaston town line. (Thomaston, it should be noted, extends a finger south along the Naugatuck River. Check it out, bottom right – I’m sure there’s some historical wrangling that took place for Thomaston to grab the land on the eastern side of the river… And I’m sure I’ll learn about that some day. Some day.)

But I was in Thomaston to hike. The parking area at the trailhead holds a few cars, but it’s on a totally sketchy curve on a hill on a road where I’m sure everyone speeds. People always ponder about my safety on my hikes… but backing into a little dirt pull off along Mount Tobe Road was by far the most dangerous moment of my day.

Hitting the trail

Safely parked, I hit the trail. It starts along an unimproved old woods road and after a slight ascent, passes near a rather nice pavilion in the woods. I trudged up there to see about it, but found nothing of note. I have no idea what that thing is doing in the woods here.

Random woodland pavilion

Shortly thereafter, I hit the junction with the connector trail that takes hikers down the hill to Waterbury Road and the Naugatuck River, crosses the river and then up a hill to connect with the Jericho Trail. I turned right, sticking with the Whitestone Cliffs Trail.

wce.jpgI hadn’t noticed before, but the trail is – duh – named after the white cliffs (which happen to be stone) it traverses. These can be seen from Route 8 around Exit 37 if you’re ever in the area. Once the loop begins (I went with clockwise this time), it climbs up the unnamed 750 foot hill to the top of the cliffs. There is one 15 foot section where hands are needed.

It’s lovely on top. Well, I should say, “It’s lovely on top but the viewshed is a bit littered with Route 8 and other development.” But that would kind of ruin it, wouldn’t it? Speaking of ruining thing… Once on top I was hit with an assault of patchouli. Note: I HATE patchouli. Not only do I simply hate the smell, it conjures of scent memories of annoying hippies in college, so it’s a double whammy.


I stopped and listened for bongos or Fritos being crunched or the unmistakable clop-clop of Birkenstocks. I heard nothing. I didn’t want to actually find the hippies, I was trying to avoid them, wherever they were hiding up up there. There are many side trails and cool overlooks up there, some of them quite hidden away. Put it this way: The amount of pachouli in air was so voluminous that it masked the marijuana they were undoubtedly toking up.


Hmmm… “Toke.” And I parked on “Mt. Tobe Road.” Who wants to bet me they get a good giggle out of saying, “Hey man, wanna meet up on Mt. Toke Road at 4:20?” Oh those hippies… So clever.

wci.jpgBecause of the stench in the air, I didn’t hang out too long and hit the trail again, still going north. It descends to a boggy area and then winds its way around and down the hill into some unfortunate ATV/dirt bike damaged areas. I chuckled to myself at the thought of Waterbury ATV’ers crossing paths with the trust fund hippies – it’s surely happened before. Eyeing each other warily, both knowing their both doing something fun yet mildly illegal. Good times.

For some odd reason, the trail meanders almost all the way out to Mt. Tobe Road and then turns back away from it. I say “odd” because I think I’d have cut that corner and not gone so close to the road; if only to give one the sense they are truly in the woods a bit more.

See how close to the road?

Anyway, there is a nice stream crossing with a little waterfall and a huge rock wall as a backdrop. It was a pretty little scene – and as we all know by now, the trail then ascended the rock wall and walked along the top, only to drop back down the backside and rejoin the loop after a stretch through some dense laurel.


At less than 2 miles, this short trail has some nice views, one decent little rock scramble and a nice woodland brook respite. While it’s certainly not the best of the three (four if you include the connector trail) Waterbury Area Trails, it’s still worth a quick hike.

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6 responses to “Whitestone Cliffs Trail”

  1. Larry Stowe says:

    Thanks for the pictures and amusing commentary! The patchouli aroma has dissipated as of 9/5/09!

  2. john g white says:

    Hi – here are a few facts about the Whitestone Cliffs trail that most people are not aware of -

    About 30 or more years ago the state allowed an archery club to use the system for their ‘games’and the gazebo was constructed for them as a rallaying point. The woods beyond the gazebo are strewn with range markers, although most have now rotted away.

    There is an old quarry on the west side of the white cliffs that was used by the Naugatuck railroad in the 1840s, as a source of stone for the construction of bridge abuttments. An old map I came across showed a RR spur built up the side of the mountain about 300 yards or so to allow stone blocks to be lowered to the tracks below.

    The white cliffs and the area surrounding them are very active geologically. One day I was sitting on the cliff when I heard a loud thump and the bedrock seemed to move a bit. The area to the south of the cliffs also show such ‘activity’ because the earth has slipped in some places along the edge of the cliff overlooking Spruce Brook Road. That area also contains two large ground faults 30-40 feet long, eight feet wide, and 6-7 feet deep. The entire ‘disturbance’ is about 80-90 feet long, and minimized at the eastern end.

    Incidentally when you first enter the trail, about 70-80 yards from the parking area the trail turns a bit and become quite steep. The ridge above reveals a stone cellar depression of an old house. An old story tells of a man that may have lived there having been murdered by a local indian. This was supposed to have happened in around 1700 or so and although there IS a record of someone having been mudered in that general area by an indian, there is no solid evidence that he had lived in this particular area. So it is best to take the story with a grain of salt.

    I had seen bears in the area south of the cliffs. A few of them gather in a a small swamp area near a pine grove, and if you go there the odor of bear is unmistakable.

    In all, the white cliffs is an excellent hike and provided a real nice view if the valley below even though it is mainly of the highway – John White

  3. Steve says:

    John –

    Great info, thanks. I love this stuff (obviously) and my plan for world (errr, CT) domination is to have comments like this from readers on every page.


  4. Hiker says:


    I was at the place, but I’m having trouble finding the cliffs.

    From the pavilion, I went up and left. This led me to the power lines south of the cliffs.

    Next time, where should I go? Is there are trail leading to the right hand side from the pavilion?

  5. Redneck says:

    I’ve hiked the Whitestone Cliffs, Jericho, and connector trail and have noted something very interesting. John g white spoke of a quarry west of the cliffs. The guy who lives in the house next to the connector trail told me that near the top of the mountain is an old steam boiler. I have never seen it myself but he is a reliable source so I trust his word. However I HAVE seen other remnants. If you go in about a 1/2 mile back from Waterbury Road on the connector trail, then go off the trail to the east until you get to the peak of the mountain, there is bedrock showing through the topsoil with drill rods sticking out of it. There are 2 rods (each sticking 2 feet out of the ground) that I know of located roughly 100 yards apart. You will also find huge chunks of rock on the surface with drill marks in them.

    I love trying to piece together history!

  6. D.James says:

    As anyone who has hiked this area will tell you, this is some of the most rugged territory anywhere,especially for the bushwacker.Filled with repeating ridges and ravines of similar features, a dense canopy and tangled understory, this area kept the French and Dutch 50 miles apart for decades, each unable to cross the “no mans land” even though they were at war. Early history of the Naugatuck Valley.

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