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Writer's pictureJill McMahon

Madame Sherri's Forest, Chesterfield, NH


Stone staircase from the ruins of Madame Sherri's castle in the woods of Chesterfield, NH

When I first saw a photo of the free standing spiral staircase tucked in the woods of New Hampshire, it was promptly added to my list of must-see ruins on hiking trails. Two years later, I finally checked Madame Sherri's castle off my bucket list and it was well worth the almost three hour drive from Portland.


I wouldn't normally drive this far for a smaller hike, but I needed a dog-friendly trail in south western New Hampshire for the hiking guide I'm working on and this gave me the perfect excuse. As it turns out, I also needed a long drive by myself to listen to music and sing at the top of my lungs. The overstimulation of the first full week of school (for both me and our boys) had left me a bit depleted. Between the drive, some castle exploration and a peaceful two hours in the woods, this trip was exactly the re-set I needed.


There are many hiking options in these woods, but I'm going to share the 4+ mile Ann Stokes Loop and Daniels Mountain Loop. For other routes in this network, visit the Society for the Protection of New Hampshire Forests here. The 513-acre Madame Sherri Forest also abuts the 847-acre Wantastiquet State Forest with many more miles of trails, including the 50 mile Wantastiquet-Monadnock Hiking Trail (WMT), which can now be hiked from Brattleboro to Mt. Monadnock. Learn more about this trail and the Wantastiquet-Monadnock Coalition here. If you're looking for a longer hiking challenge that involves some overnights in a tent, this may be something to explore. But for this post, we'll stick with a shorter option.


The Ann Stokes and Daniels Mountain loops include much more than castle ruins. Here you will find quiet woods, summit views and two ponds....one with easy access for your dog.


Dog swimming at Indian Pond, located at Madame Sherri's Forest in Chesterfield, NH.
Indian Pond off the Ann Stokes Loop at Madame Sherri Forest

The parking for this trail is off of Gulf Road in West Chesterfield, NH. Find directions and a map on All Trails here. The GPS will take you to parking for the Wantastiquet Mountain Trail, but upon arrival, you'll see a kiosk with information on Madame Sherri and her house in the woods. Just beyond the kiosk is a bridge crossing a stream and leading to the start of the trail.


Just beyond the bridge is a fork in the trail. Take the short trail to the right, to explore the castle ruins first, or save it for the end of your hike. I decided to sandwich my hike with castle ruins, because I just can't get enough of a tangible remnant of history and all that it sparks in the imagination. Since I started and ended with the castle, I got to view it with the morning, then the afternoon light. I was hoping to catch the ghost of Madame Sherri resting on the stone steps in her fancy hat, but no luck there. Here's a picture of what Madame Sherri and her castle looked like in the roaring 20's. I'll get to the history on this fascinating woman later.



The castle is now roped off at the front, since the top section of the staircase collapsed in 2021. However, there is a trail leading around the backside of the ruins and you can also explore the foundation and old fireplace at the top.



Once you've had a chance to circumnavigate the ruins, return to the start of the trail and follow the Wantastiquet Mtn Trail past a small pond on the left.



At the next fork, take a left towards the Daniels Mountain Trail, marked by white diamond trail markers. You'll follow the loop clockwise and reach the summit at 1.4 miles. There is an even better view at the Moon Edge overlook about 1.8 miles in. Here are pictures from both.



At just over 2.5 miles, you will complete the Daniels Mtn Loop and take a left to connect with the Ann Stokes loop. At 3.5 miles, you'll arrive at the junction with the Mt. Wantastiquet Trail. Take a left to follow a short trail that leads to Indian Pond. It's a sweet spot and great place for a dog to cool off. Once you've returned to the Ann Stokes trail, it's just a short distance back to the trailhead...or castle, if you want another look.


Now for the history on Madame Sherri...

This information was found on the trailhead kiosk. I'll summarize for you, since there is a lot of info, but you can get all of the nitty gritty details when you come here yourself.


Madame Sherri was born in France in 1878 and began her singing and dancing career in French music halls. She moved to New York in 1911, then in 1916 opened a series of "couture houses" named "House of Sherri". She and her husband designed colorful costumes for royalty and produced shows for the vaudeville circuit. Madame Sherri had a favorite spot in the woods of New Hampshire where there was a summer party scene at the home of a friend. She bought a large parcel of land, including Indian Pond, and built what was known as "The Castle", for the summer entertainment of friends, theatrical actors, and clothing models from New York. By the late 30's and early 40's, Madame Sherri was chauffeured through the roads of Chesterfield and Brattleboro in her 1927 creme colored Packard Touring Car wearing a fur coat, hats, feathers and a roll of cash in her bosom. But by the late 1940's, the party came to end due to financial trouble. In 1959, the castle was vandalized and in 1962, the castle burned to the ground.


Madame Sherri died in 1965 and shortly after the property was purchased by Ann Stokes, who continued to host parties and dances at the castle remains. In 1996, she donated the property to the Society for the Protection of New Hampshire Forests. Today, the Castle continues to be a destination for photographers, film makers, weddings and ghost hunters.


Stone staircase from Madame Sherri's castle ruins in Chesterfield, NH.

The Ann Stokes Loop and Daniels Mountain Loop was 4.4 miles and took me about two hours. For a shorter hike, opt for the Ann Stokes loop only, which is two miles round-trip and still includes views, Indian Pond and the Castle ruins. These woods were quiet, beautiful and I'm sure it was just my wild imagination, but the sound of the wind in the leaves here sounded more like footsteps in the leaves. If you're at all intrigued by this forest like I was, you may want to visit sooner than later. I hope the staircase holds strong for years to come, but as with Madame Sherri's wild parties, nothing lasts forever.



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