If you ask Bill Doolittle where he’s from, he might answer with a question first. A bit of local trivia: he was born in the United States, but not in a state. Washington, DC – a fitting beginning for someone whose life has never followed a predictable path.
His father, a Woodmont native, met his mother at American University after World War II. By the mid-1950s, they had settled in Milford with what would become a bustling household of five children, their parents, and a grandfather under one roof. “A typical, large family of the 50s,” Doolittle recalls. “We made Milford home.”
His two sisters, Peggy and Patty, and two brothers, John and Richard, have led successful lives filled with teaching, serving, growing, and guiding. At the center of it all were his parents – especially his father, an educator who became principal of the Lenox Ave School in Devon and later served on the Milford Board of Education.
Following in his father’s footsteps, Bill taught fifth grade for seven years in Redding before he moved into the private sector helping lead companies like PHH, Kinko’s, Global Experience Specialists, and Bombardier through expansions and turnarounds. At Kinko’s, he built an 800-person commercial sales organization from scratch before it was acquired by FedEx for $2.3 billion. At his final company, he lead the design and fabrication of trade show exhibits for global events including the Vancouver and London Olympics and the Harry Potter World Tour. During his career, he and the family relocated thirteen times.
Despite numerous experiences that took them all over the globe, Bill and his wife, Pam, always considered Milford their foundation. “While we did leave in 1982 and return officially in 2013, Milford has always been home for my family – Katie and Nathan, Jimmy, Alexis, Gabriel and Sebastian,” he says.
Bill describes Pam as the rock of his family and his life. They met at the First Church of Christ, where both families have worshipped for generations. Years later, they were married there. Last year, they celebrated their 50th wedding anniversary.
Beyond business and service, Bill is a man of many talents and interests. He has been a vocalist with The Vocal Majority, a nationally recognized a cappella ensemble that has sung for Presidents and locations around the world, recorded with the Mormon Tabernacle Choir, opened a restored theater for Microsoft co-founder Paul Allen, and produced over 20 albums – now on display in Bill’s third-floor loft. He’s also an avid golfer, a trumpet player, and a man whose office doubles as a museum of a life well-traveled.
Amidst such a storied past, Bill often reflects on what it means to have started out and returned to Milford:
“Folks from Milford reminisce about their growing years, the influence Milford has had on their lives, and how they enjoy coming ‘home,’” he says. “It’s really a special place for that.”
Now, Doolittle remains in motion. He and Pam live on the beach at East Broadway, in a home built on a property her grandfather purchased after the Hurricane of 1938. He continues a more personal fight. “My passion right now is continuing the ‘stomp the monster’ health challenge I have been fighting since 2007,” he says, referring to his long battle with Parkinson’s and Stage III prostate cancer. He works out five days a week, visits Memorial Sloan Kettering regularly, and reaches out to others newly navigating similar diagnoses — offering the kind of encouragement only someone who has walked the road can give.
That commitment shows up in the work he continues to do. As a trustee of the First Church, he served as a project manager on the restoration of its 200-year-old Meeting House steeple — a $500,000 effort completed last summer. He managed it all, including many climbs up the scaffolding to the weathervane. “My fingerprints are still embedded in some of the steelwork,” he says.
To some, it might look like an impressive bucket list. But Bill frames it differently. “I believe it is more of an obligation rather than curiosity,” he says. “For all the city has provided for me and my extended family for so many years.”
Still, what surprises him most is not the breadth of his experiences, but the speed of them. “I’m frequently reminded not to let my 28-year-old brain get in the way of my 75-year-old body,” he jokes.
Bill’s life, layered with decades of movement, service, and memory, reads like a living archive of Milford itself. A “Renaissance Man” for the modern era, Bill is proof that a life fully lived leaves fingerprints everywhere – on steelwork, on stages, and on the people lucky enough to know him.
"A typical, large family of the 50s...We made Milford home.”