Madame Sherri's Castle
In an effort to get out in the woods before all the foliage was gone, my friends and I recently traipsed across the Chesterfield Bridge to Madame Sherri's Forest to see some color and explore what remains of Madame Sherri's 'Castle' in the woods. Madame Antoinette Sherri, as just about everybody knows, was a costume designer for the Ziegfeld Follies during the 1920s. In the late 20s, after the death of her husband Andre, she had an eccentric summer house built for herself up in the woods of Chesterfield where she summered (and later lived) for 30 years.

Apparently, her lifestyle, dress, and exotic French accent caused a bit of comment around town, so much so that she became a legend even to this day. The story most repeated is that she sometimes drove around town in the summer wearing nothing but a fur coat. Some have even gone so far as to suggest that she wasn't called Madame just because she was French, but that is merely idle rumor I'm sure.
We arrived at the parking area in the midafternoon. The woods were still and quiet, and the sun mostly obscured by clouds. After spending a few minutes reading the historical material posted there, we continued across the bridge bordering the 'frog pond' and up the hill to Madame Sherri's Forest. Her house, or what remains of it, is just off the main trail, hardly a hike at all. The most prominent feature is a disembodied stone staircase, winding up to where a second floor balcony used to be. It's a slightly eerie sight, especially on a cloudy day with the trees shedding yellow leaves all around it.

A more rustic set of wide stone steps leads up to what must have been the side porch, while the remains of the driveway lead around the side to a large stone foyer. We later learned that this foyer was built so that a tree could remain inside the entrance way, it's crown growing up out of a hole in the porch roof. The ground floor of the house is still strongly suggested and surrounded by the original stonework of the house's outer walls. Anyway, there we were, in Madame Sherri's house, however much open to the sky.
After a thorough exploration of the ruins and grounds, we took the trail behind the house, winding up to an old stone spring set on the hill behind the house. There was still water trickling in at the bottom, and we took the opportunity to rest before heading further up (and up) the hill. At the summit we came to a rocky outcropping that affords a very nice view of the hills back toward Brattleboro, making the trek worthwhile.
Still not hiked out, we decided to retrace our steps and head back out the Ann Stokes trail and Indian Pond, which sounded somewhat intriguing as well. Thus we returned to the trail below Madame Sherri's and followed it alongside the frog pond and up through the woods until we reached a sign for Ann Stokes Loop trail, which helpfully directed us the remaining half a mile to Indian Pond.

Indian Pond is quite pretty and would make a very pleasant picnic spot with plenty of flat open places from which to view the water. The water was placid and reflective the day were were there, which was fortunate given the plethora of leafy colors there to reflect. We enjoyed the view for a while, wondered if we'd see a moose, didn't, and then headed back.
In the parking lot once more, we stopped to look at the pictures of Madame Sherri's house in its heyday, and happened to spot the newspaper article reporting the fire at the 'Castle.' According to the article, the house burned to the ground on October 18, 1962. The date of our visit? October 17. So we just happened to be there on the eve of that anniversary. Quelle coincidence!
Retreat Woods Tower and Cemetery
For a slightly spooky walk right here in Brattleboro, look no further than the Retreat Woods where any trail you take will eventually get you to the Tower if you follow it long enough. The stone tower, visible from Retreat Meadows, was built by patients at the Retreat back in the late 1800s. One wonders if they were made to carry the stones up the hill themselves. I rather hope not as its quite a climb. Legend has it that some of the patients hurled themselves to their deaths off this very tower, and perhaps the story is true. In any event, the tower door is kept locked, except for a couple viewing periods each year, when visitors are allowed to climb to the top on the old spiral staircase. (I've never done it, but I'm told it's dark.) Even without climbing the tower, you get a nice view over town and across to Wantastiquet just by standing on the ledge behind it, especially in late fall and winter when the leaves are down.
Once you've finished enjoying the tower, you can take the trail leading down to the cemetery (either the right or left-hand trails will do). There you will find yourself winding down the hill along a narrow path, past a large boulder covered with moss, down some steep and slippery stone steps, past the hollow tree where the chipmunks live, to the old pump building, and finally to the foot of the hill. There, if you turn to the right, you will see an old town cemetery, now very decrepit but full of worn and lichened gravestones, some upright, some in pieces. If you wander around, you can still make out the engraving on a lot of them. Keep going to your right and you will find yourself safe once more, on Chase St. just off Oak.

Although ruins are always a bit spooky, I am sorry to say that we had no strange encounters at either Madame Sherri's or the cemetery the days we went. But with Halloween around the corner, who knows what spirits might be haunting about when you visit there yourself.