Wachusett Mountain: an 1899 state reservation, skied since the 1930s

Lift-served skiing at Wachusett began after Christmas 1962, with two T-Bars eventually in operation, and a $45,000 base lodge opened for the 1964-65 season. On August 16, 1968, Ralph Crowley and Normand Letarte formed Wachusett Mountain Associates and won a five-year lease from the Commonwealth to operate the ski area, with a winning bid of $16,002, following the 1967-68 season. A major expansion began in 1982, including new chairlift installations; by the 1983-84 season the Summit Area had opened and the base lodge had been expanded to 24,000 square feet, which New England Ski History describes as making Wachusett "the largest ski area east of the Connecticut River in Massachusetts." Wachusett installed the Polar Express in 1994, described by that source as "Massachusetts' first high speed quad," cutting the ride time to the summit from about 10 minutes to about 5 minutes. In August 1995, a stand of 295-year-old oak trees was discovered in an area planned for trail expansion, and the planned expansion was abandoned as a result. A Sierra Club lawsuit over the mountain's old-growth forest resulted in a court injunction in 2000; the disputed Vickery Bowl terrain did not open until 2003, after what New England Ski History calls "years of red tape and protesting." Ralph Crowley, who had led Wachusett Mountain Associates since 1968, died on December 14, 1996, at age 71; by that time three of his children were managing the resort's operations.

David Ignatious Crowley Sr. died on November 20, 2024, at age 69, at his family's home in Princeton, Massachusetts, after nearly 50 years working in the ski industry; the resort's own tribute page credits him with growing Wachusett from a small local ski hill into a widely known mid-sized ski resort. Under his guidance, per that page, Wachusett won a national marketing award in 1999 for its internet-based sales and promotion campaign, and he originated mountain events including the "24-hour Ski Days" and the "World's Largest Ski Lesson," along with value-pass concepts including the Century Pass and a discount program known as the GPS Club.

Wachusett Meadow Wildlife Sanctuary, per Mass Audubon's own page, is a 1,220-acre former farmstead in Princeton with woodlands, wetlands, and meadows; its historic buildings and barns remain in use for educational programming, and resident sheep graze its pastures. Redemption Rock, per The Trustees of Reservations' own page, is a quarter-acre Princeton property whose granite ledge and inscription commemorate the 1676 release of Mary Rowlandson during King Philip's War; the site is a link in the 92-mile Mid-State Trail, open free daily from sunrise to sunset.