Holderness, NH- Charles Woolsey S. Conover II, 89, passed away peacefully at his beloved Squam Lake home in Holderness, New Hampshire, on September 11, 2026, surrounded by loved ones. The youngest of Woolsey Sr. and Anne R. Conover's three children, he was born in New Haven, CT, on March 25, 1937, and raised along the tidal marshes of the East River in Guilford, CT. He graduated from the Hopkins Grammar School in New Haven in 1955 and Princeton University in 1959, after which he embarked on a successful business career in the insurance industry. The love of his life, Beatrice Kittridge, came along when he interned at Connecticut General Insurance during the summer of 1958. They married on October 1, 1960, and had two sons, Charlie (1963) and Bill (1967). After chapters in West Hartford and Simsbury, CT, and in Pittsburgh, PA, the family moved to suburban Boston, MA, in 1969.

In 1971, Woolsey made the pivotal decision to join a start-up firm called Consolidated Group Trust (CGT), specializing in health insurance for employees of small businesses. Due in large part to his tireless efforts, CGT survived the economic downturn of the late 1970s and early 1980s and took off in the 1980s and 1990s. In 1976, he and Bea built a summer home in Holderness, kindling the ardent love for New Hampshire's mountains and lakes that he passed on to his children and grandchildren.

Woolsey retired relatively young in 1996 and turned his business talents toward philanthropy-a core value instilled in him as a child by his mother-by helping found the Community Foundation for Metrowest in 1995; that organization has since awarded grants totaling over $37 million to more than a thousand nonprofits in the suburbs west of Boston. While his philanthropic activity blossomed through the 1990s and 2000s in the areas of children & family services, New Hampshire environmental conservation, and the arts, he also found time to hone his gifts for oil painting, finding an artistic mentor and lifelong friend in David Ratner. His muse was the rural countryside of New Hampshire's Lakes Region; he loved nothing better than to paint a mountain or lake scene and give the artwork away to the person who would cherish it most.

In 2002, Woolsey and Bea moved permanently to "Lakewood," the home they built on the shores of Squam. There they indulged their passions for family, friends, philanthropy, outdoor activities, entertaining, and travel... along with his skeptical but constant love for the Boston Red Sox. Exceedingly proud of his sons' careers and families, Woolsey closely followed the pathways of his four beloved grandchildren. "I want to live long enough to see where each one of them is headed in life," he would exclaim. Bea's health struggles in recent years were a great blow, but he persevered with optimism, love, and good cheer. As his own health failed beginning in December, 2025, he never wavered in his life's purpose: "I have more people to help, more people to love."

Woolsey is survived by Bea, his devoted wife of almost 66 years, and by his older brother, Scott (he was preceded in death by his older sister Clare). He is also survived by sons Charlie (Sharon) and Bill (Deb); grandchildren Beatrice (34), Arthur (31), Emma (31), and Nellie (26); and two great-granddaughters, Sage (4) and Ruthie (2 months). He leaves behind a vast constellation of friends around Boston, Holderness, and across the country, so many of whom stood in firm and loving support for him. His and Bea's incredible caregiving team constantly extolled his warmth, kindness, and generosity.

A celebration of life for Woolsey will be held on Saturday, October 10, at 2:00 p.m., at the Plymouth Congregational UCC (4 Post Office Square, Plymouth, NH).

In lieu of flowers, memorial contributions may be made to Camp Hale, a program of United South End Settlements which was near to Woolsey's heart. Gifts will help ensure that future generations of children can experience the joy, growth, and sense of belonging that Camp Hale has provided for more than 125 years. Donations may be made online at https://pro.gofundme.com/give/568376#!/donation/checkout or by mailing a check payable to Camp Hale to:

United South End Settlements

Attn: Camp Hale

48 Rutland Street

Boston, MA 02118

Please include 'In Honor of Woolsey Conover' in the memo line.