More than you ever wanted to know about the Apple Tree Inn

The Apple Tree Inn has a long and fun history, and uncovering it is an ongoing treasure hunt for me! The property is currently 21.5 acres and has 3 structures, but has been through many different iterations over the last 140 years:

I don’t know anything yet about the property before 1885.

I’ll start by talking about the western half of the property:

In 1885, a woman named Cecile Bristed built the building we call the Main House. She used it as a vacation home and called it The Orchard. Bristed was a great-grandaughter of John Jacob Astor through his first daughter Magdalena and though the circumstances of Cecile’s birth are somewhat unclear to me (I suspect she may have been born out of wedlock), she shows up in family wills and in the social pages as a fancy dinner party guest here and there. The house was designed by the noted Pittsfield architect H. Neill Wilson, who also designed the neighboring estate Shadowbrook (the one-time the largest private house in America and last residence of Andrew Carnegie. It burned in 1956) and Cecile’s brother Charles Astor Bristed’s house just down the road, Lakeside (still standing). There was also a large carriage house located behind the house that I assume was built at the same time the house was built but I do not know. It is no longer standing but I think it was located where the upper parking lot is now.

In 1892, Bristed sold the home to Clarence Andrews (whose wife eventually divorced him and married the son of Chester A. Arthur, 21st president). I don’t know much else about Clarence Andrews yet.

In 1898, Andrews sold it to a member of an old New York family, Henry Pease, and his wife Katharine di Pollone, the daughter of Camille di Pollone, the Count of Turin (Italy). Their 1895 wedding had been touted by the New York Times as “the most brilliant wedding that had taken place in Stockbridge for many years.” Pease attended Harvard and Columbia and practiced law for two years before “retiring” and presumably living on his family fortune. When they moved in, the Peases added a billiards room and a master suite for themselves (now the Ostrich Room and the luxurious Room 8 above it). The Peases were definitely a “couple about town,” and they show up in the guestbooks of many prominent families of the era including their friends the Vanderbilts. They did not have any children. The Peases vacationed at The Orchard for more than three decades. Henry died in the home in August 1937 and Katharine sold it in November 1946.

Now we will switch gears and look into the eastern half of the property.

Around 1890, a man named Henry Barclay built a vacation house on the eastern part property and called it Bonnie Brae (not to be confused with Bonnie Brier in Stockbridge). It is no longer standing–it was located where the event lawn now is–but its carriage house is still there: it is the hotel’s current maintenance garage and owners quarters. Bonnie Brae was an especially beautiful house with 20 rooms and was the site of a number of famous balls reported on in the New York Times, including a notorious “stable ball” thrown in the carriage house.

I don’t know when Barclay sold. At some point, there was a three-cornered transaction with Madison Square Mortgage Co. and David Green, and the house was sold to a man named Eliphalet Davis.

In 1907, Henry Clews, the enormously wealthy head of the Henry Clews & Co. banking house, who was a personal friend of Abraham Lincoln and economic adviser to Ulysses Grant, bought Bonnie Brae as a gift for his daughter.

In 1919, Clews put the house up for sale and it was purchased by Gaston Drake, a lumber magnate whose firm supplied much of the wood used in the development of the city of Miami. He renamed it Astalula (cited at least once in the press, I think erroneously, as Ashtula).

On March 1, 1946, Drake sold it to C. Joralemon Rollins who, on July 7, 1946, opened it as the Rollins Theater School. He had moved the school to Lenox from its prior home in East Hampton, NY after ten years there. The school used the house as an administrative building and used the carriage house as its theater.

In 1946 the properties were united for the first time: In November of that year, the theater school expanded by purchasing the Orchard to use as a residence for the director of the school and its carriage house (no longer standing) to use as additional student housing. I think it was at this point that the Orchard was renamed “the West House” and Bonnie Brae was renamed “the East House.” The union was short-lived however, as Rollins shut the theater school in 1948 and sold off the two parcels separately:

In 1948, the East House was purchased by Lorna & Kenneth Sheldon who operated it as a B&B called Hawthorne Hill.

I don’t understand yet what happened to the West House between 1948 and 1952, but in 1952 it was purchased by Roy “Skip” Rappaport who was 26 years old at the time and turned the West House into a summer inn called Avaloch. Avaloch is a variation of Avalon, a mythical island in Arthurian legend that had many apple trees on it, a nod, I think, to the original name the Orchard. Avaloch may also mean “above the lake,” which would be fitting considering the hotel’s position over the Stockbridge Bowl. In 1954, Rappaport (his mother actually) bought the eastern parcel from the Sheldons and the two properties were united for good.

The property seemed to have something of a golden era under Rappaport who ran it for seven summer seasons and later led a second career as a famous anthropologist and served as chair of the anthropology department at University of Michigan. In a bit of foreshadowing, he brought Margaret Mead to the hotel as part of a speakers series in 1952. Rappaport also opened the famous-at-the-time Five Reasons Steak & Ale House serving beer and sandwiches until late in the night after Tanglewood shows.

“If all be true that I do think,
There are five reasons we should drink;
Good wine—a friend—or being dry—
Or lest we should be by and by—
Or any other reason why.”
Henry Aldrich, ‘Reasons for Drinking’ (1689)

In late 1958, Rappaport sold the property to the Avaloch Realty trust, with trustee L. George Reder. On April 8, 1959, Avaloch Realty Trust sold it to Frederick M. Myers, Jr.

For the 1959 season only it was operated by Don Soviero (I’m not sure if there was another sale or if Fred Myers & Don Soviero were partners?) who owned Bousquet Mountain and later went on to run the famous Music Inn, host of a litany of world-class jazz, folk, blues, and rock performers. On September 30, 1959, Soviero sold Avaloch to Michael Bakwin, trustee of Berkshire Avaloch Realty Trust in a swap for a property he owned on Rte 183 in Stockbridge that I don’t really understand yet but I think has something to do with the Music Inn.

In 1963, Bakwin added the Round Room, originally as a porch I think, and in 1966 built the 21-room structure that is now called the Annex (alternately the Lodge and the Motel). At some point he also built a small ski lift, the top of which is still there in the woods behind the hotel! He also continued to run the Five Reasons with success and played host to summer residencies with jazz greats such as Randy Weston.

In February 1970, Bakwin sold the property to Max Wasserman (Wasserman Development Corp.) who demolished the East House (and part of the East House carriage house) that March and tried but failed to turn the property into a resort (or condos?). On July 10, 1974, Wasserman sold it to Richard E. Ross.

Ross sold it to Alice Brock, made famous by Arlo Guthrie’s folk anthem Alice’s Restaurant. She ran the property under the name “Alice’s at Avaloch” and it was the third and final Alice’s restaurant. From Fall 1965 - April 1966, Alice operated her first restaurant, called the Back Room–this is the one that the song was written about and it was located at the site of the current Theresa’s Stockbridge Cafe in downtown Stockbridge. Then from 1971 - ?, she ran her second restaurant, Take Out Alice, in a former package store which is now a private home at 43 Glendale Rd in Housatonic. Then she bought Avaloch from Ross in September 1975 and ran it through the summer of 1978. I have met many lovely people who worked and partied at the hotel in the Alice era. By the end I think she was sick of the place and left the area forever, relocating to Provincetown where she died in November 2024. I was lucky enough to get to meet her for the first time two days before she died and saw for myself a small glimpse of the fiery energy that made her famous.

In 1979 the inn was purchased from the bank by Alan Carr, who ran it under the name Portofino for three years and I know very little about this period so far.

In 1983 it was bought by a couple from New York — the Smiths. The Smiths operated the tavern as the McIntosh Tavern and moved the pool to its current, beautiful location. In 1995, after 12 years of ownership, they were looking to sell so they hired a broker-friend from New York, Joel Catalano, whose wife, Sharon Walker, loved the property so much that she and Joel ended up buying it themselves.

In 2021, after 25 years, Joel & Sharon sold the hotel to Max and James Khaghan, two brothers from New York. They reimagined the tavern as the Ostrich Room, upgraded to more modern decor, installed fast Wi-Fi, and — crucially — connected the buildings to the town sewer!

And in April 2024, Claire bought the hotel from them and became obsessed with its history in the process!

Many thanks to Sharon Walker, James K, Cornelia Gilder, Amy Lafave, and above all Alison Adams for helping me piece together what I know so far. Thanks to the many others whom I have interviewed or who have swung by the hotel to tell tales. I look forward to continuing to learn from all of you! If you have other information or especially photographs, please email me at info@appletreeinnlenox.com.

Last updated January 2025.