Cover photo for Robert "Rob" Happy's Obituary
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1955 Robert 2020

Robert "Rob" Happy

June 28, 1955 — June 18, 2020

RUTLAND – Robert P. Happy, 64, beloved husband of Kimberly Happy, passed away in his wife’s loving arms on June 18, 2020, after an 8 month hard fought battle from complications of open-heart surgery. Robert was born in Worcester and was the son of Paul W. and Barbara Brandt Happy.

Robert was a graduate of W. Boylston High School, and earned his bachelor’s degree from Westfield State and a Masters Degree in criminal justice from Anna Maria College. He is a registered Native American Cherokee Indian. Bob served as a police officer for 36 years, beginning his career in W. Boylston and serving over 30 years in Sterling, retiring in 2013 as a highly regarded Police Sergeant.

As a teenager, Bob had a great passion for ice hockey and played in several leagues. He grew up as a neighbor to Wachusett Country Club in W. Boylston, caddying at a young age and growing a love for golf. Bob played golf on his W. Boylston High School team, winning championships. He continued his love for both sports as an adult playing golf with his best buddies, Bill, Pat and Dave and sometimes spending more time in the woods coming out with pockets full of treasured golf balls. Bob cherished the opportunity to join the State Police in competing against the retired Boston Bruins. He remained an active player with the Rusty Blades. He was a member of the W. Boylston Congregational Church.

Robert will be lovingly missed by his wife, Kimberly J. (Toupin) Happy; his parents, Paul W. and Barbara Brandt Happy of Sterling; his sister, Paula R. (Happy) Gilmore and her husband Bruce Gilmore; his step children, Ryan and Emmersyn; his six children, Derek, Garrett, Danielle, Marc, Paul and CJ; three grandchildren; his mother and father-in-law, Bill and Joan Toupin; in-laws, Jackie, Steve, Darcy, John, Scott and Christine; his adored nieces and nephews; and his beloved cat, Abigail and Maltese dog, Romeo.

Bob and his wife enjoyed life together going to the gym, hiking, walking and spending time in Brewster. He found great pleasure in digging clams with his wife and in-laws, Bill and Joan. He cherished his time with them on Cape Cod. He was always certain to fill his bird feeders every day as he enjoyed their sweet songs. Bob found his “happy” place around wonderful family and friends, everyone falling in love with his most endearing smile and bellowing laugh…

Robert’s life will be celebrated privately. Funeral arrangements are under the care of Miles Funeral Home, 1158 Main Street, Holden. www.milesfuneralhome.com

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