Winnie the Poo
The Fifty-Acre Wood, Woodstock
November 2024
After driving through northern Woodstock along Redhead Hill Road, then English Neighborhood Road, you come to Pond Factory Road. You immediately think, “boy, I’m taking this skinny gravel road to Massachusetts, there can’t be much up this road!”
But you know you’re heading towards CFPA’s Wabbaquasset Trail, so the woodsy scenes only make sense. You pass a trailhead and park, without thinking too much about it at all. Grab your water, lock up, and hit the trail.
Then you see the sign that you’re at a place called The Fifty-Acre Wood and are immediately confused. “There are two separate and distinct loop trails on this tiny road to nowhere?
Apparently, yes.
This is what I’ve come to call a bonus hike… so let’s hike!
This 50-acre wooded property donated to the Town of Woodstock by the Darby family in memory Herbert C. and Virginia Darby in 2001, features an easy 1.5 mile loop trail.
The Hundred Acre Wood of the Winnie-the-Pooh stories was inspired by Five Hundred Acre Wood in Ashdown Forest in East Sussex, England. After driving on English Neighborhood Road, I thought there was some tie-in, but there is not.
Since I didn’t know I’d be hiking this trail 10 minutes earlier, I Googled and read my friend Matt’s summer of 2022 description on his excellent Explore Connecticut site: “The Fifty Acre Wood is close to being a forgotten town trail, but features great forested sections and beautiful fern views of Beaver Pond.”
There were no ferns in November, and for a good 20 minutes or so, I thought the trail had seen a rebirth of sorts in the two years since Matt’s visit. The trail was cleared well and although the blazes were spotty for long stretches, it was easy enough to follow.
I took a right at the split to begin a counterclockwise loop. I could see the beaver pond off to my left as I descended through the woods. There is a disturbing number of old rusted carcasses of farm equipment, trucks, and machine parts in these woods. I have no idea how or why, but clearly there must have been some sort of factory around here at some point.
What was the name of the road I came in on again? Oh yeah, Pond Factory Road.
Well, if this Pond Factory is responsible for all this tetanus and crap in these rather nice woods, then the Pond Factory doesn’t deserve a road named after it.
I neared Leavitt Road and skirted some old stone walls and the woods really opened up here. It’s pleasant, I must say. The loop looped back on itself, now closer to the pond. And each year, that pond will get closer and closer to the trail. (In fact, it was clear that the pond had eaten some of the trail already, and this was after six months of drought.)
These are active beavers… eager beavers if you will. Maybe the old rusty cars and trucks will stop them at some point. The trail gets harder and harder to follow in this section, perhaps because it has been naturally rerouted by the beaver activity over the years.
At one point, a couple massive blowdowns forced me off trail and it took me a long time to refind it. Likely because it’s kinda nonexistent here for a bit. I had a good sense of where I was, and knew the upper loop was straight up the steep hill, so I kept on my way where I felt the trail should be and after a bit, voila. There it was.
I’m glad I kept true here, because this last stretch before heading up to the intersection and the trail back out to my car was a really quite nice stand of white pines.
It really wouldn’t take that much to revitalize this place. It’s a nice trail that affords some interesting natural views as well as some interesting old factory junk, if you’re into that. And if you’re on your way up to hike the Wabbaquasset Trail, which I recommend, you have to pass this place, so you might as well spend the half hour tackling it too.
Just be sure to do the loop clockwise or you might give up in short order. Which would be so Eeyore of you.
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