Bruce H. Tobey

Bruce H. Tobey obituary, Gloucester, MA

Bruce H. Tobey

Bruce Tobey Obituary

Obituary published on Legacy.com by Greely Funeral Home on Feb. 21, 2026.
Bruce Tobey, Gloucester's longest serving mayor, died on Tuesday, February 17, at his home, surrounded by his family, after a long illness. He was 73 years old.

Bruce Tobey devoted his life to serving the community where he was born on January 19, 1953, to Robert D. Tobey and Lillian Foley Tobey. He attended Gloucester public schools, graduating from Gloucester High School in 1971, where he was president of his class. He went on to Wesleyan University, graduating in 1975, with a joint major in Russian and Soviet Studies. He was a proud member of Delta Kappa Epsilon Fraternity. He received his law degree from Suffolk University in 1978.

Throughout his college and law school years, Bruce worked on the Gloucester waterfront at the old dehyde plant, forging friendships that would last a lifetime.

He then enlisted in the U.S. Coast Guard, serving as a lieutenant in the Judge Advocate Generals Corps on Governor's Island in New York City. It was there that he met Patricia Wolleben who would become his wife in 1982.

Moving back to Gloucester with Pat, Bruce began his career in public service as the City Solicitor for Mayor Leo Alper. He was elected to the Gloucester City Council in 1988. While serving on the Council in 1991, Bruce was chosen by his fellow councilors to fill the unexpired term of Mayor William Squillace. He pledged not to seek election as mayor in that year's municipal election, running instead for the school committee.

Two years later, though, he did run successfully for mayor and served until 2002. His tenure was marked by numerous accomplishments including the long-delayed expansion of Blackburn Industrial Park, the completion of the controversial sewer extension into North Gloucester, the reclaiming of the Magnolia dump for soccer fields and the long anticipated completion of the Fisherman's Wives statue looking out onto Gloucester Harbor. Tobey had a knack for bringing together people with opposing interests and helping them create a common path forward for the good of the whole community.

During the observance of Gloucester's 375th Anniversary in 1998, Mayor Tobey spearheaded an ambitious sculpture show in City Hall, bringing together the works of sculptors both local and of international renown. Skeptics thought it too ambitious, but Bruce prevailed and the show was an extraordinary success.

While serving as Mayor, Bruce was president of the Massachusetts Municipal Association and chair of the Advisory Council of the National League of Cities. He served as chairman of the Commonwealth of Massachusetts Local Government Advisory Committee, the Commonwealth's Federal Stimulus Task Force and the Massachusetts Water Infrastructure Finance Commission, as well as on numerous advisory committees for the U.S. Environmental Protection Agency.

After stepping away from the mayor's office in 2002. Bruce went back to Suffolk University for an MBA in 2004. He then returned to public service in Gloucester, serving as an at-large councilor until 2014, when he entered the private practice of law, specializing in environmental law and wastewater management. He was a principal in Tobey Project Management and of counsel to the law firm of Pannone, Lopes, Devereaux and O'Gara. In 2023 he stepped back into public life as tri-chair of the 400th Anniversary of Gloucester's founding by the Dorchester Bay Company in 1623. Perhaps his proudest achievement of that commemoration was the nationalization ceremony at Tablet Rock where dozens of immigrants became United States citizens.

While his professional accomplishments were lengthy, it was the life he built with his wife Pat that brought him the most pride. He was a devoted father to his four daughters, and he never shied away from an opportunity to update colleagues and friends on their achievements. The stories he most recently loved to share were those of his 10 grandchildren. To them, he was lovingly referred to as "Junior" and he could do no wrong in their eyes. Whether it was dressing up for Halloween in homemade costumes, telling stories of his travels, watching them thrive in their personal pursuits, or simply sitting on the floor to indulge them in building their latest creation, he always embraced the silliness and joy that are so important to childhood. He was looking forward to welcoming two more grandchildren to the family this spring.

He was an avid gardener who had a knack for making even the smallest of spaces beautiful. On a sunny summer day, you could always find him on Good Harbor Beach. The third boardwalk will never be the same without him. While Gloucester was his home, he was an avid traveler who embraced any chance to explore another part of the world. A lifelong learner, his travels were often fueled by his love of history and he crafted itineraries that allowed him to better understand the people and events that shaped the environment.

Bruce Tobey is survived by his wife Patricia Wolleben Tobey, with whom he shared 44 years of marriage; their four daughters and their families: Emily and her husband Salvatore DiMercurio, their daughters Lilliana, Stella and Amelia; Dana Tobey and her husband Shawn Medeiros, their daughter Clare; Melanie Tobey and her husband Dominic Golini, their children Jackson, Henry, Mia and Leo; Pamela Tobey and her husband Christopher Lindberg, their sons Michael and Charlie; his brother Robert Tobey, niece Jennifer Tobey, cousins Everett and Tom Brown and numerous extended family on his wife's side.

He was predeceased by his parents and his sister Kathryn Tobey, sister-in-law Cynthia Tobey, sister-in-law Mary Wolleben and brother-in-law Charles McMahon.

There will be a celebration of Bruce's life in the summer, his favorite season. In lieu of flowers, contributions in his memory may be made to the American Cancer Society, American Alzheimer's Association, or National Multiple Sclerosis Association.

To plant trees in memory, please visit the Sympathy Store.

Sign Bruce Tobey's Guest Book

Not sure what to say?

February 24, 2026

Jack Reilly posted to the memorial.

February 23, 2026

Lisa Wasson posted to the memorial.

February 22, 2026

Wendy Brown posted to the memorial.

4 Entries

Jack Reilly

February 24, 2026

Pat and the girls. I am very sorry to hear this news. I have many fond memories of bruce going back to the Grange. Really smart very funny and oh man did he love his family. Very sorry

Lisa Wasson

February 23, 2026

Dear Pat and girls,
I´m so sad to see that Bruce has passed away. He was truly one of my favorite people during my years living in Gloucester. Always fun, always helpful, and always so devoted to you all. He was such a proud dad. And a great gardener!
Sending you hugs...
Lisa Wasson
(Mom of Liz, Sarah and Jay Nearis)

Wendy Brown

February 22, 2026

I'm so sorry for your loss
I just wanted to send my condolences to Bruce's family and friends. Rest in peace my friend

Sam Cleaves

February 21, 2026

Condolences to the family and such a big loss for Gloucester. I have many good memories of working under Bruce back in the 1990s as the city's conservation agent and then city planner. Rest in peace, Bruce.

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Greely Funeral Home

212 Washington Street, Gloucester, MA 01930

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Sign Bruce Tobey's Guest Book

Not sure what to say?

February 24, 2026

Jack Reilly posted to the memorial.

February 23, 2026

Lisa Wasson posted to the memorial.

February 22, 2026

Wendy Brown posted to the memorial.