Skiing at Eastover Resort in the 1960s
Eastover Resort
Lenox, Massachusetts
Status: Lost/Defunct
First Season:1954-55
Last Season:1990s
Vertical Drop:165 feet
Standing Lifts:
Past Lifts:1 double, surface lifts
Left: Skiing at Eastover Resort in the 1960s
Recent News:
Located in Lenox in the Berkshires of Massachusetts, the Eastover Resort was once home to an alpine ski area.

Fahnestock Mansion and Duncan School for Boys

The origins of the Eastover Resort date back to 1910, when a brick mansion was constructed in Lenox as a summer home for Harris Fahnestock. Following the sale of the property in 1941, it became home to the Duncan School for Boys until 1944.

In 1946, George Bisacca purchased the 500 acre property and developed a recreational resort centered around the mansion. The Eastover Resort opened in 1947.

Eastover Develops Skiing

A significant investment was made in winter in 1954-55, when a new rope tow and indoor swimming pool were advertised. By the time 1956-57 rolled around, Eastover featured two rope tows. Snowmaking may have also been added around this time.

A major expansion took place in 1964, when Bisacca decided to step up Eastover's skiing operation. 14,000 cubic yards of filled were hauled in, resulting in the development of the Shenandoah and Tally-Ho trails. Serving the expanded area was a new 1,500 foot Hall double chairlift, as well as a 700 foot rope tow. A 2,000 foot toboggan run was also offered.

End of Skiing

Bisacca's daughters Ticki and Susan took over the resort following his death in 1983. As the 1990s approached, the ski area's operations may have become increasingly sporadic. While the chairlift was still advertised as late as 1998-99, it may have ceased operating as early as 1995-96.

Circa 2002, the double chairlift was sold to nearby Bousquet. Bousquet also offered free skiing for Eastover guests for a few seasons.

In March of 2004, Ticki and her daughters bought out her sister Susan and continued to operate the resort. After five years of ownership, economic problems, as well as an unsuccessful search for a buyer, resulted in the family closing the resort in November of 2009.

The H.G. October Mountain Group purchased the property in early 2010 and reopened it later that year.

There are no known plans to redevelop the Eastover Resort ski area.

Click on lift name for information and photos
Standing Lifts

Past Lifts
Chairlift - Double - Fixed

Visitor Memories
"My Dad worked there when he retired from the Mass state police. He was close with George and lived on site in the cabin at the bottom of small ski slope with Loring. I remember the toboggan run with the right hand turn (before they straighten it out). The faculty softball game. Tally Ho with revolving stage. I remember they bought a bunch of school buses and built a train for the parade every year in Lenox. It was a great place for me to visit with my Dad. I actually spent time with the McNinch family across the street. I believe Bob married one of the daughters. We would swim in the pond at the house. I loved the civil war museum and the "tunnel" loaded with memorabilia. Eastover will never be the same. It was a BLAST!!!! "
Michael Boutiette, May. 9, 2021
"Went there in the 60’s with a large from Philadelphia,Pa. and what a fantastic time we all had. Wish I could hear from other folks who were there when we were there. What great memories I have of Eastover."
Al Moschella , Feb. 23, 2021
"A true holiday find. That I haven’t come across since. Any senior East overs I should. Or would like to know about,,,,,,,,,,"
Mary Mylett, Jan. 12, 2021
"I was introduced to Eastover on the weekend of July 4th 1979. It was nothing but food and fun and partying all weekend and going to the Tally Ho Barn to listen to the bands on the revolving stage from 8pm-3am ..... GREAT MEMORIES."
Peter Mucci, Oct. 15, 2020
"I had great times at the resort from 1967 to 1971. Dancing with live music Horse barn was converted to a huge dance hall Horseback riding golf walking trails water sports swimming pool. Group meals. The Calvary charge by the confederates. Two nites with room and meals $28. Plus drove past Norman Rockwell’s studio every weekend for 5 years and never stopped to buy a $10 painting now worth in the millions😀"
Gene Fontanella, Aug. 22, 2020
"I worked there from 1952 until 1956. Worked in the kitchen under Chef Harry Sharpin for two summers, then was a waiter for three summers. Best job I ever had. In 2017 I published a book about Eastover titled From May to September See it on Amazon. Wish someone would do a screenplay from it.... "
jim lynch, Aug. 27, 2019
"July 4, 1988 , Came from Boston , to go relax and party there, the staff used to go for beer and booze runs so no one would have to drive, met my wife there who was from neighboring Newton, been 30 years , but memories there , I will never forget, sorry to hear your closing , loved this place THANK YOU "
Paul Curran , Aug. 18, 2019
"Worked there on the grounds crew during the summer of 1957. I was one of those southern college kids that came there for a great summer. Had a great summer and would meet the beer man at the end of work days and get a 6 pack of Reingold beer. He would keep a tab and would collect on paydays. On Saturdays we played bell hop and would meet the train and bring all the good looking northern girls to the mantion. On the evenings we were encouraged to dance with them and entertain them. Sure was fun. We always participated in all the civil war stuff George put on. I stayed in a cabin with 2 fraternity brothers from University of Tennessee. It was a great time. Carl Redmon, 2019. "
Carl Redmon, Apr. 28, 2019
"I learned to ski and ice skate at Eastover. Our family went ever year from 1969-1982. The owners kids became friends and it was a super anticipated trip every year for a reunion with all the same families . Hopefully one day I’ll get to come back from the west coast and visit ."
Rob Vuona , Mar. 1, 2019
"I had the biggest crush on Loring! Our group, the Skunks, teased me incessantly about it. My friend and I win a costume contest dressed as “Black and Blue”, the theme song. She all in blue and I in black leotards. In the barn was where I first heard the Kingston Trio sing “Svotch and Sida”. And remember the alcohol was in the honor system?"
Laureen Campbell, Jul. 28, 2018
"My husband And I were married there in 1995. We went back every year to celebrate our anniversary. We made many friends on our stays at eastover. We were very heartbroken when they decided to close down. "
Nancy Millett , Jul. 3, 2018
"Me and my frends from Brooklyn n.y. went there in the late 60 great memories especially when Loring sang his favorite song also the sing alongs at happy hour the hay rides so many memories met really great friends sorry to see that great things change all the best to everyone who were lucky to go there "
Joseph Caggiano, Jun. 9, 2018
"Worked there while atteding Lenox Memorial High in the mid seventies one of the best times of my life."
Stanley Hayes, Feb. 19, 2018
"first visit was our honeymoon in June, 1949. Met friends then and are still friends though our numbers are dwindling. remember Claude as our waiter. "
bill leonard, Mar. 2, 2017
"I was just cleaning out some old boxes and came across an Eastover brochure from the ‘70’s and decided to “Google” Eastover to see if it was still in operation. My buddies & I from Jersey used to visit Eastover on singles weekends most every winter and always had a blast. The winter sports were fun but the drinking and dancing in the Barn and the folk groups in the Tally Ho building were the best! I still remember singing about “Poor Old Charlie” and the MTA in the converted horse stables. So many great memories. Sad to see it is no longer a ski resort. "
Mike Nicoletti, Dec. 29, 2016
"I remember going to Eastover on a singles w/e. In 1972 or 73 and meeting a young staff member named Caryl not sure of the last name, this was at the Tally-Ho barn. It was a lot of fun, glad to see you are still doing business. Best regards; Rob "
Rob Pitts-Robertsson, Dec. 27, 2016
TOM CAVANAUGH, Dec. 9, 2016
"I have great memories of 1988 I met my husband Michael Zorbo he was the landscaper.I also had i great time with all my friends from New Jersey.Michael passed away last September and I miss him every day but I have great memories of him."
Jean Zorbo (frischknecht), Oct. 14, 2016
"In 1960, Eastover was the very first vacation I ever took as a young working woman (pre-college). My best friend and I were 18 and took the train, stayed on the third floor, loved the costume contests...I can't tell you how many bottles of champagne we won. I was Elvis one year and George's wonderful dog was "Hound Dog." I remember the great Red Robinson band and one of their favorite songs, "Black and Blue." Greased watermelons in the pool along with other relays. All the handsome college boys waiting tables for the summer. And, of course, the most fantastic mountain setting. An unforgettable time and place. "
Mary Flynn, Sep. 9, 2016
"Went there in the early60's.What a great place.Would party all weekend."
Arthur Jaskowiak , Aug. 18, 2016
"Eastover brings back soooooooooooo many great memories, especially on the Halloween and St. Patrick's weekends. Would travel there from New Jersey with my friend and meet up with a group of tire salesmen from Connecticut. The staff truly worked hard. Would love to know what that group from Connecticut are doing today. "
Debbie Bellas, Jun. 7, 2016
"Eastover was special to me. I am a graduate of St Joseph High School in Pittsfield and we did our after prom party there. What a great time we had for so many years. "
John Bashara, Mar. 19, 2016
"To those who knew Peps Gugino for the 50 years he went to Eastover I want to let you know that my uncle passed away on Tues Mar 8,2016 at the age of 98 3/4 years old. Eastover was his joy. He made such good life-long friends. To them I want to say thank you for bringing such happiness in his life.Eloise"
Joseph Gugino, Mar. 14, 2016
"I had a marvelous time at Eastover a very long time around the late 40's, early 50's. All the girls fell in love with George Bisacca, of course, and he and his wife were very indulgent of our crushes! It was a small, intimate group that was family. Nice!"
Thelma Santoro, Dec. 30, 2015
"omg!eastover!!!! hahahaa! 4x with different groups of friends the halloween weekends were by far my favorite memories how the poor staff ever put up with us and many others haha! we always had loads of fun loads of drinks loads of men ! hahaa! to many funny fun memories even skinny dipped! !!! thank you for the fun memories that my kids will never know of !!! ha!"
jean keough, Nov. 25, 2015
"Eastover will always be a special place for me. I was there once with our family of seven in February of 1968. The mansion was cavernous to me and the memories come back after reading what other people have written. I remember the large group meals and having hot chocolate each morning. I can still picture the museum in the basement. I also remember swimming in the indoor pool just off the learning slope. I think there was a window just inside the building which allowed us to look into the pool like an aquarium.(Accurate?) As kids we went to bed early so our parents could go join the adult festivities. Most importantly, I put on skis for the first time at Eastover. My three days on the bunny slope evolved into a lifelong hobby and trips with my own family to ski resorts across New England and Utah. My time there was short but I thank Eastover for the memories."
Jeff Kaplan, Jul. 22, 2015
"We enjoyed Eastover Resort for about 10 years in the 70's. We have many memories about the dancing, partying and just have a great wild time. We came as a group of about 20 from Falmouth MA. Just many great memories we could not forget."
Edward Parfumorse, Jun. 21, 2015
"I spend many winters vacationing a Eastover in the late 70s.As a tween, I found myself playing in the civil war room or sliding down the hill on the old wooden tobogan. I still have picture showing me getting pulled up the rope tow becoming the newest member of the polar bear club - only those who vacationed there would understand. It is and always will be my Grand Budapest. Thank you for the fond memories."
Christopher Casey, Apr. 11, 2015
"I was a guest all year because my father was a very close friend with George Bisacca. I was their almost every weekend either feeding the buffalo or gathering their remains for my fathers garden. George was a great man and taught me how to ride his famous tobaggan run standing up! William Night was the operator of the tram which brought up the hill to a cozy lodge with plenty of hot chocolate. The inside pool & sauna were waiting after. The Civil War museum downstairs was truly an experience in which I will never forget. My High School Prom (St. Joseph High School) was held at Eastover. Thanks to my father who worked at the Berkshire Eagle who annually had their Christmas party held at this resort. I am in my 60's now and nothing but fond and wonderful times & memories that George, family and staff provided me & my family for so many years. It is hard to find such resorts with make you feel at home as The 'Eastover Resort'. William R. Meade"
William Meade, Mar. 29, 2015
"I have fond memories working at Eastover during the summers in the 1960's while in college. I remember Tiki and Susan very well and worked in the kitchen for Mickey. "
Emery Baker, Mar. 10, 2015
"My husband and I met at eastOver in the late 60's. My friends and I have such great memories of so many fun times spent there. Thanks for the memories..."
Phyllis Miedler, Feb. 13, 2015
"Worked there in summers of 57' and 58, was a great time between years in college. Hated to come home at end of summer . Great memories."
Charlie Harris, Oct. 29, 2014
"My family (including aunts,uncles and cousins) went to eastover every Christmas from about 1959 to 1969. Favorite memories include the taboggan run,horseback riding, and swimming. As a young teen we had incredible freedom. We hung out on the Rathskeller, listened to music and stole soda that was always under lock and key also I remember burgers and hot dogs late at night in the barn only great memories"
Phyllis Hoffman, Jul. 6, 2014
"Our family went there for over 30 years total...this included 2 generations of our family ...if I HAD to choose 2 memories....they would be these....we welcomed Y2K there(both generations represented) and helped it go out with a bang at Oktoberfest 2009. My dad Zeke loved the place and when we lost Eastover it was like losing him all over again some 18 years later!"
William Marsden Jr, Jul. 5, 2014
"Where do I begin, so many memories, good times and yes, insanity. It was our weekend of things you never did at home around your kids, it was all the things you told them not to do. So many nights singing, partying, just having unsupervised FUN!!!! We went every year at least one time per year for many years, some of our group are no longer with us, but oh those happy times. Thanks for the memories"
Donna Pugsley, May. 26, 2014
"Eastover was a yearly winter family event when we were kids in the late 60's, early 70's. Our family consisted of tons of cousins, aunts and uncles on my mother's side of the family. These memories are still talked about today. We would go from Monday to Friday and enjoy skiing, horseback riding, ice skating and tobagganing. We also remember sleigh riding down Shenandoah at night in the pitch dark while our parents were inside hanging at the bar. We would come in from the cold and travel through the hall of pictures to find our parents. We also talk about the rooms we stayed in and the free soda. So much fun and so many amazing memories were made!!"
Katherine Russo Kearney, Mar. 12, 2014
"Went on a ski weekend with the company I worked for 'Western Electric'. Was the best time of my life, especially when you are with someone you care about very much. The dancing was great, the music was great, everything was great. I particularly remember the toboggan slide and afterwards trying to get back to the top of the hill, such fun. Just wondering if your archives have group pictures stored away for the following years 1958, 59 and 60. Best time of my life."
Isabella Romeo, Aug. 30, 2013
"My husband & I came with a large group for at least 20 yrs for a winter weekend away--we skied, did tobogganing, swam in the pool, went outside in our bathing suits in January, ate, drank, danced from 4-6 every night, rested & went back for more dancing from 9pm-2am--loved the turning stage with the north & south flags flying from each band, the cannon that Loring & George set off every Saturday night, the laughter, fun, blazing fireplaces, small band in the stables singing songs we all knew in a cozy atmosphere, the pictures, the food eaten with friends, etc etc. We liked it so much we brought our kids up for a summer & a winter weekend together--then when we had 9 grandkids we brought them & their parents to Eastover every year for 8 years till the year our favorite "
Jeanne Thomas, Jul. 20, 2013
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External Links
  • Eastover Resort - official site
  • Eastover Resort - New England Lost Ski Areas Project
  • Last updated: November 6, 2016

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