Woolsey was one of the original founders of the Foundation for MetroWest in 1995 and was Chairman of the Board from 1995-2000. He was a Founder and Principal of Consolidated Group Trust headquartered in Framingham, an employee benefits administration company with over 800 employees at the time of its sale in 1996. While residing in Massachusetts from 1969 to 2009 he was a Director and Board Chair of both the Metrowest YMCA and the Metrowest Chamber of Commerce, a Trustee of the Danforth Museum of Art and the Rivers School, a Director of the Massachusetts Board of Higher Education, Chair of the Board of Governors for the Copley (Art) Society of Boston and a Director of the Appalachian Mountain Club. He has held governing roles with NH Public Radio, the Lakes Region Conservation Trust, the Museum of the White Mountains and advisory roles with numerous other non-profit organizations since moving to New Hampshire with Bea.
