Robert "Woodie" Woodbury's Obituary
Robert “Woodie” Woodbury, 83, passed away peacefully on May 25, 2026, in Bonita Springs, Florida. Born on February 10, 1943, in Bangor, Maine, to Henrietta and Harold Woodbury, Robert lived a life defined by dedication to his family, his career, and his passions.
Bob grew up in Orono, Maine, where he graduated from Orono High School in 1961. A talented athlete, he was later honored with induction into the Orono High School Athletic Hall of Fame in 2019. Following high school, he attended MCI Prep in Pittsfield, Maine (1962), and pursued higher education at the University of Maine - Orono, earning a Bachelor of Science degree in 1966 and a Master of Education degree in 1967.
Bob's professional career began at Friend’s Academy in Glen Cove, Long Island, New York (1966-67). However, the call home brought him back to Maine after just one year. He accepted a position at Belfast Area High School (1967-68) before moving on to Old Town High School (1968-74). At Old Town, Robert became the youngest Class LL League coach at the time—a remarkable achievement. He served as Faculty Manager and basketball coach for four years while also holding an assistant coaching position for basketball at Husson University in Bangor 73-74.
In 1974, Bob began what would become his lifelong role as Athletic Director at Sandwich High School in Sandwich, Massachusetts. During his 25-year tenure (1974–1999), he made a lasting impact on the school’s athletic program. He first coached boys’ basketball from 1974 to 1976, then later returned to coach girls’ basketball when the school needed a coach. There, he found his true calling, leading his teams to more than 200 wins and mentoring many athletes who went on to compete at Division I universities. Under his leadership, Sandwich High School moved from the Cape & Islands League to the more competitive South Shore League, helping raise the program’s level of success. The athletic program also grew from 10 teams to more than 25, winning numerous championships. Budget restraints resulted in Bob bringing “Billy Burr’s Carnival” aka Sandwich Town Fair as a money maker for student atheletics. This became an annual event. Among his proudest achievements were bringing football to Sandwich High School and introducing pickleball in physical education classes well before it became widely popular.
Outside of his professional career, Bob was an entrepreneur who founded Woodbury Lawn Service—the first of its kind based in Sandwich. He also remained active in sports through pick-up games and slow-pitch softball, playing long enough to share the field with his two sons.
After retiring in 1999 following a near-fatal heart attack, Bob embraced life with his beloved wife of 64 years, Gloria Sherburne Woodbury. Together they cruised the East Coast aboard their boat, the "Gloria Dawn," before relocating from Cape Cod to Florida. They also explored 36 states and parts of Canada on their matching Honda Goldwing trikes. Later in life, Bob discovered a passion for macro photography. Self-taught and highly skilled, he produced stunning photographs and delighted family and friends with his creative photoshopped” cartoons.
Bob is survived by his devoted wife Gloria; Brother Jon C Woodbury (Barbara), Sons: Jon D Woodbury (Suzanne) and their children Hunter (Taylor) and Cole (Tory); Robert D. L. Woodbury (Jennifer) and their children Mason and Jillian; and Daughter Melissa Woodbury (Timothy Cauley) and her son Cody Sheehan. several nieces and nephews. He was predeceased by his parents Henrietta and Harold Woodbury.
A loving husband, father, grandfather, great-grandfather, loyal friend, gifted athlete, accomplished photographer, and mentor to many students and athletes—Robert’s legacy is one of dedication and joy. His memory will continue to inspire all who had the privilege of knowing him.
May his memory bring comfort to those who loved him.
A Celebration of life will be held on June 28, Sandwich Hollows Golf Club, Sandwich MA Noon to 3PM. In Lieu of flowers donations may be made to a Youth League of your choice.
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