ROCKPORT — Bob Rosenberg was born in New York City on December 16, 1940. With his parents, and later his younger brother Paul, he lived in Dayton, Ohio, Great Neck, New York, Miami Beach, Florida, and Boston, Massachusetts. His mother, Esther (Mickey) Rosenberg was a homemaker, and his father, Benjamin, was a first-generation American from a long line of Eastern European Orthodox rabbis, whose professional career was in Jewish philanthropy.   

Bob graduated from Miami Beach High School in 1958. The classmates had a lasting love for each other and memories of their halcyon days in the Florida sun. Bob attended many reunions and stayed in contact with them and members of his Keystone fraternity. Bob was voted “Most Handsome” in his senior class, which remained a point of pride.

Throughout his childhood and teen years, Bob spent summers at Buckskin Camp for Boys, just outside of Ellsworth, Maine. He spoke often and glowingly of his happy memories of camp, and was proud to have achieved the distinction of Junior Maine Guide on his first attempt. 

Bob graduated from Cornell in 1963, and attended Northwestern University Dental School where he completed his DDS. He married Karen Waterman of Chicago in 1967, and joined the United States Air Force. The couple moved to Newburgh, NY, where Bob practiced dentistry in the service, and had a daughter, Tory. After his honorable discharge they moved to the Boston area, and he earned a graduate degree in orthodontics from Tufts University. 

In 1973 Bob married Joan Gordon, and together they moved to her hometown of Rockland, Maine. There he opened an orthodontic practice on the corner of Beech and Broadway.  The family lived above the office until they moved to Pen Bay Acres a bit later, and still later to their residence on Chestnut Street in Camden. They had three daughters—Erika, Hilary, and Whitney, who were raised in the Maine way — skiing, sailing, and fostering a lifelong appreciation for the beauty of Maine. 

Bob treated patients in Rockland, Camden, and Belfast for over fifty years--in some families he put braces on multiple generations—retiring at age 81. He considered it an ethical imperative to accept all forms of payment and insurance, consistent with his belief in social justice and the Jewish value of Tikkun Olam, meaning “repair of the world.” He was a life-long Democrat and a member of Adas Yoshuron Synagogue in Rockland for over 50 years. 

A perennial athlete, Bob was a member of the swim team in high school, and became a serious runner after college, completing 12 marathons, including Boston, and later cycling. He rode in the Trek Across Maine 26 years in a row. He became an accomplished ballroom dancer. Bob was an active Rotarian with over 25 years of perfect attendance in West Bay Rotary. He loved to play cribbage with his family, poker with his buddies, and bridge with local friends. He was handsome, romantic, and funny. He loved art, beautiful (particularly classic) cars, and music—especially Van Morrison, Dire Straits, the Rolling Stones, classic country, and 50s rock and roll. 

In 1994, he met Hillary Waterman and they married in 2000. In their 32 years together, they shared interests and passions including reading, skiing, Jewish study, travel and language learning, cycling, love of their pets, the beach, learning the ukulele, ballroom dancing, food, especially ice cream, and wine. He loved his step-daughter, Katy and called her a daughter along with his own. 

In 2019 Bob was delighted to learn of and be reunited with another daughter, Carolyn, bringing the total to an even half dozen, and the two enjoyed seven years getting to know and appreciate each other. 

Bob died at Maine Medical Center in Portland on June 16, 2026, surrounded by his family and his much-loved little dog, Rocky, after a period of acute illness. He was exactly eighty-five and a half, and still making plans for the future—in recent months, he had expressed a desire to bike across Italy (for the second time), and also return to the dance floor.

He is survived by his devoted wife Hillary Waterman, and the daughters of whom he was so proud: Carolyn Garson of Pennsylvania (with wife Mary Remer and daughter Anna Garson); Tory Waterman of Chicago; Erika Dixon (with husband Dan and son Edmund) of Orono, Maine; Hilary Rosenberg (with children Payson Smith and Piper Smith) of California; Whitney Rosenberg of Portland, Maine; and step-daughter Kathleen Rose of Portland, Maine.

He leaves his brother, Paul Rosenberg and sister-in-law Harriet Moss of Boston, as well as cousins around the country. Special lifelong friends include Dave and Suzan Theriault, Bill and Susan Barbour, and Eddie and Carol Miller, from the Rockland area, and Arthur Lane of Florida.

Bob maintained strong ties with so many classmates and friends, old and new, from all of the years and communities of his active and engaged life—a rich life, robustly savored, and well lived—a life he was not ready to depart, and from which those who loved him were not prepared to lose him. He will be forever missed and remembered.