William Robert “Bob” MacGregor

KENNEBUNK – William Robert “Bob” MacGregor, 97, passed away peacefully on Jan. 2, 2024.

Bob had a huge presence and led an extraordinary life. Born in Vassalboro, he and his family soon moved to Malden, Mass. where he graduated from Malden High 1944. He then served his country in the U.S. Army, and was later a proud graduate of Tufts University 1949. After college Bob became a social worker, reaching out to the Dukes, a gang on the streets of Boston, Mass. He mentored these young men, counseled them and took them on adventures like hiking in the White Mountains.

While in Boston, Mass. he met Harriet Bassett, a preschool teacher, also serving the community. They became engaged at the Bull & Finch (the Cheers bar) and married soon after. Bob and Harriet moved to Danvers, Mass. and raised their family. He became a Juvenile Probation Officer at Salem District Court and rose through his career to be appointed Deputy Commissioner of Probation for the state of Massachusetts.

Upon retirement he headed to the mountains in his size 16 boots and hiked the AT, the Long Trail and “bagged” all of the 4000 footers in New England. He and Harriet continued to heed the call of service and joined the Peace Corps serving in Tunisia, Africa working in an orphanage. Later they made many trips to the Dominican Republic with the Intercultural Nursing Association, assisting in schools and clinics. In Maine, Bob worked on several houses with Habitat for Humanity.

As an accomplished carpenter, Bob always had a project. He spent three summers building a 26 foot sailboat in the backyard in Danvers, Mass. He then built a small cabin, using only hand tools, on Pleasant Lake in Otisfield, and in 1990, he built their new retirement home in New Gloucester where they moved to and lived for many years. Camp and home were filled with his custom furniture.

Bob was a lifelong learner and an avid reader of one or two books per week. He was deeply knowledgeable about American History, the Founding Fathers and the precarious nature of our democracy. He did the NYT crossword regularly, studied etymology and recently took up pool, yoga and watercolor painting.

Ultimately, Bob’s greatest project and legacy is his large and loving family. He leaves behind his loving wife of 71 years, Harriet; daughters Karen L. MacGregor and Jan (John) Miliano, son, Bill (Karen P.) MacGregor, son-in-law, Tom Johnson; and sister, Jean (Arthur) Hebert. He was “Grandbob” to many, including nine grandchildren; and 12 great-grandchildren.

Bob was predeceased by daughter, Kathy MacGregor (Tom) in 2005 and son-in-law, Peter Sargent (Karen L.) in 2014.

The family is grateful for the support and kindness from the outstanding staff and fellow residents at Huntington Common in Kennebunk.

At Bob’s request there will be no service, but certainly a good deed, a walk in the woods or embracing a new adventure would be a fitting way to honor him.

To share a memory or leave a message of condolence please visit Bob’s Book of Memories Page at http://www.bibberfuneral.com.

Arrangements are in the care of Bibber Memorial Chapel, 67 Summer St., Kennebunk, ME 04043.