Berkshire Resort Set To Close
The Eagle article interviews Dorothy H. "Ticki" Winsor whose father started the resort. She has lived their for 62 years of her live and her children and grandchildren were born there. Many of the employees have been working at Eastover for decades. Increased operating costs and local and state regulations made it hard for the family to afford the upkeep of the 500-acre resort.
The resort accommodated guests in a variety of rooms from dorms to luxury suites in the mansion. It operated differently than most resorts offering weeks aimed at singles, families and other specific groups. It also did not have a liquor license so guests had to BYOB.
Eastover has been the site of many weddings and other events and served as the site of the Massachusetts Special Olympic Winter Games for more than 20 years. The cannon at Eastover is the one that the Boston Symphony Orchestra uses during its performance of Tchaikovsky's "1812 Overture" at Tanglewood every summer.