If you’re looking for unique things to do in Vermont that go well beyond the usual covered bridges and leaf-peeping, a visit to the castle ruins of Madame Sherri is one of those rare discoveries that stays with you. Just a short drive from the Inn on Putney Road, these hauntingly beautiful castle ruins sit quietly in the woods of Cheshire County, New Hampshire, waiting to tell a story that’s equal parts glamour, excess, and mystery. You’ll stop mid-hike to just take it all in, wondering how on earth something this extraordinary ended up in the middle of a New England forest.
When you’re mapping out things to do in Brattleboro, Vermont, and the surrounding region, the options are genuinely impressive. The downtown arts scene, the vibrant local food culture, the Connecticut River, and the abundance of hiking and outdoor spaces all make this corner of southern Vermont one of the most compelling destinations in New England. Whether you’re spending a long weekend or a full week, there’s an easy rhythm to days here: explore something new, eat something delicious, and come back to a place that actually feels like home. That’s where Inn on Putney Road comes in.
As one of the most beloved Brattleboro Vermont Boutique Hotels, we offer the kind of warmth and attention to detail that chain hotels simply can’t replicate. From the thoughtfully appointed guest rooms to the gourmet breakfasts and beautifully kept gardens, it’s a base camp for your Vermont adventures that you’ll actually look forward to returning to each evening. Book your stay and use it as the perfect launchpad for everything this region has to offer, including a hike to some of the most memorable castle ruins in all of New England. Book your stay today!
Madame Sherri: The Castle Ruins, the Legend, and the Woman Behind It All
Within the Madame Sherri Forest in West Chesterfield, New Hampshire, the Ann Stokes Loop Trail winds through a cathedral-like hemlock forest before arriving at one of the region’s most photographed and talked-about landmarks: the stone castle ruins of Madame Sherri’s summer home. The trail is a comfortable two-mile loop, making it accessible for most fitness levels, and the payoff at the end is genuinely special.
As hikers approach the ruins, the first thing they see is a sweeping, curved stone staircase rising dramatically up into the forest canopy, like something from a forgotten fairy tale. Further into the site of Madame Sherri’s castle ruins, the remaining stone columns, a grand fireplace, and the lower level with its great stone archways give a vivid sense of the home’s original scale and ambition.
Madame Sherri’s house, as it was known locally, was the passion project of Antoinette Bramare, born in France in 1878. She came to New York in 1911 with her husband, Anthony Macaluso, and under the stage name Antoinette DeLilas, she had already built a reputation as a performer in fashionable clubs before reinventing herself as a costume designer. Inspired by Otto Hauerbach’s hit play “Madame Sherry,” she launched her design business under the name Andre-Sherri and quickly attracted a clientele that included the legendary Florenz Ziegfeld. For nearly a decade, her costumes were among the most sought-after in New York show business.
When her husband died in 1924, the social scene she had thrived in lost its appeal. After visiting friends in West Chesterfield, she fell in love with the quiet countryside and in 1929 purchased 600 acres of land, commissioning a home that was nothing short of theatrical: an unexpected fusion of Roman grandeur and French chalet style, perched in the New Hampshire hills.
The castle became the setting for legendary parties through the late 1920s, drawing crowds from the New York social world and generating no shortage of gossip. Local stories from that era describe Madame Sherri driving through town in her cream-colored Packard, dressed in fur coats with very little underneath, and hosting gatherings that had the energy and excess of a Gatsby novel come to life.
The reckless generosity of those years eventually caught up with her. Mounting debts forced her to abandon the property, and the castle she had poured her dreams into sat empty for years before burning to the ground in 1962. The property and castle ruins were later purchased by Ann Stokes and are now maintained by the New Hampshire Society for the Preservation of Forests. What remains is a site of remarkable atmosphere, genuinely beloved by photographers, history enthusiasts, and those who appreciate the particular magic of a place that has clearly lived a big life.
The legend of Madame Sherri has grown considerably in the years since. Visitors report seeing her ghost on the stone staircase of the castle ruins, and the faint sound of music has been described more than once by people hiking through at dusk. Whether or not you believe in such things, there’s an undeniable energy to the castle ruins that makes it easy to understand why the stories have taken root. Extending your hike past the ruins leads to Indian Pond and open ledges with long views across the landscape, making for a full and satisfying day out.
Boutique Hotel Comfort in Brattleboro, Vermont
After a day of exploring castle ruins and hiking through hemlock forests, coming back to the Inn on Putney Road feels like exactly the right reward. Our gracious French Provincial manor sits in downtown Brattleboro and is one of the most distinctive Brattleboro Vermont boutique hotels you’ll find anywhere in southern Vermont. Our Boutique Hotel is refined without being stuffy, historic without feeling frozen in time, and genuinely welcoming in a way that makes guests want to come back year after year.
The guest rooms are beautifully appointed with a level of care that reflects the inn’s pride in what it offers. Every detail, from the quality of the linens to the thoughtful touches that make a room feel personal rather than generic, has been considered. The gardens surrounding the property are stunning and provide the kind of peaceful outdoor space that is increasingly rare. Mornings begin with a gourmet breakfast that sends guests out the door genuinely satisfied and ready for whatever the day holds.
The location makes our Boutique Hotel an ideal home base for exploring all the things southern Vermont has to offer. Downtown Brattleboro is walkable from the inn and packed with independent shops, galleries, outstanding restaurants, and a music and arts scene that punches well above the town’s size. Day trips to Madame Sherri Forest, the surrounding mountains, and the Connecticut River Valley are all easily managed from here. Whether your idea of a perfect Vermont day involves hiking to castle ruins, browsing a farmers’ market, or simply sitting with a good book in a beautiful garden, our Boutique Hotel Brattleboro Vermont sets the stage for all of it beautifully. Reserve your room now!
