OBITUARY: Leo P. O’Connell III, 73

Below is an obituary from Nichols Funeral Home:

WILMINGTON, MA — Leo P. O’Connell III, of Laconia, NH passed away unexpectedly on January 29th, 2023 at the age of 73.

Leo was born on July 9, 1949, and was raised in Wilmington at the “family compound” along with extended family on Faulkner & Jones Avenue. Leo graduated from Wilmington High School Class of 1967. He went on to study at Bryant-McIntosh School of Aviation. He was an accomplished leisure pilot. Leo was first introduced to the canteen truck business by his uncle and thus began Leo’s Canteen running on the streets of Cambridge and Boston under the motto of “If You Don’t Buy From Me, We Both Starve”. He was a successful businessman, but his true calling was Lake Winnipesaukee. His love affair with the lake began as an infant with his grandparents at Lake Shore Park who eventually settled in Buzzell Cove in Moultonborough, NH where Leo enjoyed many years of summer bliss. The family memories built there propelled him to move to the Lakes Region permanently midlife to join the New Hampshire Marine Patrol. His exceptional navigation skills taught to him by his grandfather earned him a position aboard the M/S Mount Washington. Leo worked his way up the ranks over many years and eventually retired as Fleet Captain from the Winnipesaukee Flagship Corporation. Retirement did not sit well with Leo and in true lake life seasonal fashion, he worked numerous side jobs over the years to contribute to the local economy as well as feed his sense of purpose and strong work ethic. His favorite activities were boating, water skiing, snow mobiling, hitting the gym daily, family parties at Hunt Road, and traveling with Tink.

Leo was a devoted family man, diligent in being a good son, husband, father, grandfather, brother, uncle, cousin, and “your best friend”. He took tremendous pride in building special relationships with each of his children and grandchildren. He fervently supported all their passions and interests. To that extent, his heart was incredibly welcoming. He abolished the term “step” and created a beautifully blended family.

Leo was the son of the late Leo P., Jr. & Marie T. (Baldwin) O’Connell. He is survived by his devoted wife of 23 years, Lucille (DiCalogero) O’Connell. His adored children, Shelley Sainato, her husband David, and Judy O’Connell of Wilmington, the late Christopher O’Connell, Leo P. O’Connell IV and his wife Brandy of Cameron, NC, Heath O’Connell of Fairport, NY, Jason O’Connell and his fiancée Kierstin Houle of Victor, NY, Lyn Devito of Dracut MA, Christopher Harkins and his wife Lisa of Everett, Danielle Harkins and her fiancé Flavio Zumpano, of Windham, NH. His cherished grandchildren, Colin, Madelynne, Carolyn, Leo Patrick V, Hazelyn, Nathaniel, Gavin, Jona, Antonio, Kaylee, Alexis, and Juliana. Loving brother of Daniel R. O’Connell & his wife Carol of Meredith, NH, the late David D. O’Connell & his late wife Anne of Lynn, Kathleen M. Galeno of Georgetown, the late Nancy E. Roberts & husband David formerly of Maine, Marie T. O’Connell of Middleborough, the late Darlene O’Connell Fleming of Maine, John J. O’Connell & his wife Amy of Gilmanton, NH and the late Charles B. O’Connell of NH. Further survived by many nieces, nephews, cousins, the extended DiCalogero family, and all his “best friends”.

Family and friends will gather for Visiting Hours at the Nichols Funeral Home, 187 Middlesex Ave. (Rte. 62), Wilmington, MA, on Friday, February 3rd from 4:00-8:00 p.m. A Mass of Christian Burial will take place on Saturday, February 4th at 10:00 a.m. in St. Dorothy’s Church, Main St. (Rte. 38), Wilmington, MA.

In lieu of flowers please consider a donation in Leo’s memory to Local Heroes, Inc., P. O. Box 536, Wilmington, MA 01887.

To leave a message of condolence for the family please visit our website at

Leo P. O'Connell III

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