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HomeLife In the BerkshiresGARY LEVEILLE: Third...

GARY LEVEILLE: Third Annual Satirical Holiday House Tour

The Southern Berkshire Hysterical Society is offering its all-new online, free frolic of some unusual homes and buildings in our area. Ho-ho-ho.

It’s that most wonderful time of year when local nonprofits offer holiday house tours as fundraisers. But not everybody can afford to attend these events, so the Southern Berkshire Hysterical Society is offering its all-new online, free frolic of some unusual homes and buildings in our area. Ho-ho-ho.

J. Paul Getty’s Hunting Cabin in Alford

J. Paul Getty’s Hunting Cabin: Petroleum patriarch J. Paul Getty enjoyed visiting and hunting in the Berkshires. Once considered the richest man in America, Getty remained frugal throughout his life. In the early 1960s, he established a modest hunting cabin in the woods of Alford, using one of his left-over oil tanks. Although the tank is now abandoned, it is considered a secret shrine by the oil and gas industry, and is occasionally visited by fawning geologists.

The Bermuda Triangle of Clayton

Clayton’s Bermuda Triangle:The mysterious three-point boundary between Canaan, Connecticut, Ashley Falls, and the hamlet of Clayton in New Marlborough has experienced strange phenomena for hundreds of years: Cattle disappear, farmers vanish in their fields, hay bales spin and localized earthquakes topple buildings. The structure shown here was rebuilt in 2016, only to be shaked, rattled and rolled once again. This past April, producers from the television program “Unsolved Mysteries” visited the site but were never seen again. 

Animal House Hotel in Sandisfield

Animal House Hotel: Back in the late 1950s, animal rights pioneer and Sandisfield resident Randy Rottweiler established an exclusive hotel for dogs owned by the rich and famous. Advertising that “dogs deserve a vacation,” Mr. Rottweiler experienced considerable success for more than a decade. He was forced out of business in 1969 when an enraged Zsa Zsa Gabor found her poodle cavorting with Hugh Hefner’s cocker spaniel. Gabor successfully sued and the mongrel mansion was shut down.

Caddyshack under Brookside Road in Great Barrington
Caddyshack, Brookside Road, Great Barrington

Caddyshack: This little-known structure has survived for more than 100 years under Brookside Road in Great Barrington. It offered golfers shelter from thunderstorms at a golf course once located just south of the road. Actually, truth is sometimes stranger than the fiction found in the rest of this holiday tour. The tunnel was actually built to allow cattle from the Truman Wheeler Farm on South Main Street (now the Great Barrington Historical Society and Bostwick Gardens) to travel to a grazing field on the other side of Brookside Road. And that field actually became the first Wyantenuck golf course.

Thoreau House near Beartown State Forest on the border between Great Barrington and Monterey

Thoreau House: Located near Beartown State Forest not far from the Monterey/Great Barrington border, this small structure was once the summer home of author, poet and transcendentalist spinster Henrietta D. Thoreau. She was perhaps best-known for her award-winning book titled “Malden,” a biography of actor Karl Malden. Known locally for her pithy sense of humor, Henrietta once told her dentist, “Please, no painkillers. I want to transcend dental medication.”

Smurf House in Sheffield

Smurf House: This charming Sheffield hideaway offers low-cost guest rooms to economy-minded visitors. The strategic hole in the roof allows romantic star-gazing for guests. Once a tavern built by Revolutionary War hero Huey Hewins, the building was purchased in 1958 by Belgium artist “Peyo” where he was inspired to create lovable cartoon characters known as the Smurfs. Some locals still refer to the place as the Smurf House.

Photosynthesis Hut in Great Barrington

Photosynthesis Hut: Established in 1972 on upper Main Street in Great Barrington, this modest structure originally housed a small drive-up flower shop. But the hut had no heat and, with winter approaching, store owner Tommy “Leo” Chong revised his business plan, cleverly changing from “Photosynthesis Hut” to “Foto Hut,” where he offered camera film and photo developing to drive-in customers. Chong prospered for a time with Foto Huts popping up around the country, but digital media eventually drove him out of business. There is no truth to the rumor that the hut is being considered for a drive-in marijuana store.

To explore previous house tours, click here and here.


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