Haunted Travel: Where to Sleep With Ghosts in the Berkshires

Room 301 at the Red Lion Inn has gained some notoriety for odd happenings.

PITTSFIELD, Mass. — In the growing culture of Halloween sales booms and rampant paratourism, I keep trying to tell people looking for spooky thrills: you're crazy if you don't visit the Berkshires, especially this time of year.

Sure, you could spend a more obvious weekend with Boston walking tours or braving Salem in the Samhain season, with all its teeming crowds and scarcity of available restrooms. Once you've tried that, and are ready for something a little more subtle, book yourself a few days of meandering roads through the orange-stained hills; legend tripping the mansions, theatres, museums and mountain trails where folks have been talking about seeing ghosts since long, long before it was big business.

For the growing market of vacationing with that flavor in mind, it's not enough just to take day tours in the places where ghosts have been hunted. They want to start off on the right foot and do their sleeping in a place where it just might be disturbed. While there's more than a dozen options in allegedly haunted accommodations from South County to North, and several more famous for this, here are my top three suggestions, purely on the basis of volume of stories heard.

Red Lion Inn

The rich history of Stockbridge's iconic Red Lion Inn is better known, but not so much its ghostly undercurrents, though murmurs of paranormal experiences have begun to attract a few more seekers to the inn over the past few years.  

Popular interest in this part of the inn's allure began to swell as it became more public nearly a decade ago, spilling out of the closet onto Trip Advisor. In an review from August 2004, a guest recounted the experience of something touching his head and tugging the bed sheet. Almost one year to the day later, a second reviewer reported several times waking up to the feeling of having their toes being pulled on, as well as the sound of footsteps and the sensation of an unseen force fluffing up the comforter. A month later, a third review described the guest being woken all night by cover-pulling from the foot of the bed. When the man turned to look, he saw a man in a top hat and "olden day attire," who then vanished in a white mist.

These three experiences all took place in Room 301, but tales of odd happenings are in no way confined to this area. Guests have told staff of unusual sightings in other rooms, and one former housekeeper stated there had been rumors among some of the cleaning staff going back at least a decade about the whole fourth floor being haunted. In addition to the man in the top hat, there are vague rumors about a ghostly young girl carrying flowers.

One incident recollected by inn staff is that of a gentleman who asked to be relocated from his room, he said, because of the sheer number of "spirited" guests he encountered. That customer turned out to be celebrity medium James van Praagh. Since these stories became even more public in 2009, several rounds of ghost hunters have made an excursion to check it out, with mixed reviews of its paranormality.

Crowne Plaza 

The final suggested lodging is the most modern, and perhaps the most surprising of purportedly haunted hotel stays in the region.  

At less than 45 years old, the Berkshire Crowne Plaza hardly seems the intuitive locale for ghost stories, and it is perhaps only this perception that has kept it from the annals of Berkshire's more illustrious hauntings, for stories of this place abound. Cold spots, unplaceable voices, and a shadowy female figure are said to have been seen all about the 179-room hostelry, from the bathrooms around its top floor ballroom to the outlying parking garage and plenty of hallways and bedrooms between.

The Crowne Plaza tower can be easily seen on South Street. The modern structure was preceded by other inns, most notably the Wendell Hotel.

A former manager from when the hotel was still a Hilton says during those days it was quite common to hear stories, sometimes even disturbed complaints, of odd occurrences throughout the building. Company policy frowned strongly on discussion of these kind of stories, and this may still be the case, as Crowne representatives have repeatedly declined to comment on these rumors.

Visitors and sometimes employees share these first or secondhand anecdotes shyly, half-embarrassed by the seemingly incongruous notion of spectral shenanigans roaming this giant phone booth-shaped box of steel and concrete raised when Nixon still president. Every cultural influence of the past century — from M.R. James to Scooby Doo to Kubrick to part-time paranormalist plumbers —  that has helped crystallize our notion of what a ghost should be seems to argue for the absurdity of this.

While the Crowne may be among the younger generation of local lodging, though, this prominent corner of Pittsfield's city center has been the site of hotel business for the better part of two centuries. The beloved Hotel Wendell was demolished where it stands during the late 1960s, after several incarnations and additions under different names and owners since 1898 (it was opened the same year the Red Lion was rebuilt). Prior to the grand Wendell, which at its height boasted more than 300 rooms, that corner of the South and West streets had bedded guests since Abner Stevens first built an inn in 1823, which eventually became the Exchange Hotel and later the United States Hotel.

It was in the downstairs kitchen of this establishment on the night of Sept. 19, 1862, that one Jane Collins, a worker there, was brutally murdered by her husband with a bayonet. At the trial, a long history of abuse by husband William was recounted, such that for some time Jane had ceased to go home at night, and had been living at the hotel for some time. She appeared to be attempting to escape the marriage at the time when Collins stormed into the hotel kitchen and things took their final tragic turn.

This is an obscure footnote, near lost in the pages of local history, an item I came upon in archived newspapers quite by accident while seeking something else. Who else knows what other stories color this spot, where thousands have slept and worked over the last 190 years? Folks around Pittsfield still report seeing spooks near the site of one of the city's long-lost haunted houses, Greenwood, and that's been burned down for more than a century. Why not the site where its most historic hotel stood?

Seven Hills Inn
 

The intricate fireplace at Seven Hills.

Just off Route 7 in Lenox, next door to the Edith Wharton's increasingly ghost-hunted manor, the historical curiosity and lore of elegant Seven Hills Inn is sometimes overlooked. Formerly Shipton Court, the property was renovated from an expanded 18th-century farmhouse to a manor house in 1911 by the eccentric Emily Spencer, and added to further to open as an inn in the 1950s. Seven Hills contains a number of interesting quirks of history, from the tucked away back tavern room where Leonard Bernstein used to hide out at the piano, to an antique safe which has remained locked for decades because none now living know the combination ... as well as other legacies, less well known.

Over the years, various guests and employees associated with the inn have reported a plethora of brief, curious sightings of odd "somethings" ... sounds, shapes moving in the kitchen at night, a woman in white seen in the window from unoccupied rooms. The music room seems to be a focal point of many anecdotes ... this typically during quiet nights in the off-season, and not to be confused with the shenanigans of wedding crowds.

Lady Spencer was unable to bear children, and this was a matter of some preoccupation in Shipton Court. A close inspection of the fine woodwork around the grand fireplace of the main parlor reveals a distinct intentionality of both Catholic and pagan fertility symbols. Around these little touches of yearning architecture would roam her pet pig, wardrobed in only the finest imported dresses as she wandered freely about the mansion in the company of a rooster, David, whose stuffed remains are kept to this day by the Lenox Historical Society.

These are just three of the top choices, but potentially phantasmic stays can be found throughout These Mysterious Hills with a little looking, in virtually every style and price range.

Pittsfield correspondent Joe Durwin is also a recorder of the county's oddities at These Mysterious Hills.

Sheffield Craftsman Offering Workshops on Windsor Chairs

By Breanna SteeleiBerkshires Staff
10:30AM / Sunday, March 29, 2026

Andrew Jack uses hand tools in his wood working shop. 

SHEFFIELD, Mass. — A new workshop is bringing woodworking classes and handmade items.

Andrew Jack specializes in Windsor chairs and has been making them for almost 20 years.

He recently opened a workshop at 292 South Main St. as a space for people to see his work and learn how to do it.

"This is sort of the next, or latest iteration of a business that I've kind of been limping along for a little while," he said. "I make Windsor chairs from scratch, and this is an effort to have a little bit more of a public-facing space, where people can see the chairs, talk about options, talking about commissions.

"I also am using it as a space to teach workshops, which for the last 10 years or so I've been trying to do out of my own personal workshop at home."

Jack graduated in 2008 from State University of New York at Purchase, and later met woodworker Curtis Buchanan, who inspired him.

"Right after I finished there, I was feeling a little lost. I wasn't sure how to make the next steps and afford a workspace. And the machine tooling that I was used to using in school." he said, "Right after I graduated, I crossed paths with a guy named Curtis Buchanan, and he was demonstrating making really refined Windsor chairs with not much more than some some flea market tools, and I saw that as a great, low overhead way to keep working with wood."

Jack moved into his workshop last month with help from his wife. He is renting the space from the owners of Magic Flute, who he says have been wonderful to work with.

"My wife actually noticed the 'for rent' sign out by the road, and she made the initial call to just see if we get some more information," he said. "It wasn't on my radar, because it felt like kind of a big leap, and sometimes that's how it's been in my life, where I just need other people to believe in me more than I do to, you know, really pull the trigger."

Jack does commissions and while most of his work is Windsor chairs, he also builds desks and tables, and does spoon carving. 

Windsor chairs are different because of the way their backs are attached into the seat instead of being a continuous leg and back frame.

"A lot of the designs that I make are on the traditional side, but I do some contemporary stuff as well. And so usually the legs are turned on a lathe and they have sort of a fancy baluster look to them, or they could be much more simple," he said. "But the solid seat that separates the undercarriage from the backrest and the arms and stuff is sort of one of the defining characteristics of a Windsor."

He hopes to help people learn the craft and says it's rewarding to see the finished product. In the future, he also hopes to host other instructors and add more designs for the workshop.

"The prime impact for the workshops is to give close instruction to people that are interested in working wood with hand tools or developing a new skill. Or seeing what's possible with proper guidance," Jack said. "Chairs are often considered some of the more difficult or complex woodworking endeavors, and maybe less so Windsor chairs, but there is a lot that goes into them, and being able to kind of demystify that, or guide people through the process is quite rewarding."

People can sign up for classes on his website; some classes are over a couple and others a couple of weekends.

"I offer a three-day class for, a much, much more simple, like perch, kind of stool, where most of the parts are kind of pre-made, and students can focus on the joinery that goes into it and the carving of the seat, again, all with hand tools. And then students will leave with their own chair," he said.

"The longer classes run similarly, although there's quite a bit more labor that goes into those. So I provide all the turned parts, legs and stretchers and posts and things, but students will do all the joinery and all the seat carving the assembly. And they'll split and shave and shape their own spindles, and any of the bent parts that go into the chair."

His gallery is open Wednesday through Sunday 10 a.m to 2 p.m., and Monday and Tuesday by appointment.