John Joseph Lupo

John Joseph Lupo, 52, of Winchendon, Massachusetts, passed away on February 24, 2026, at Hartford Hospital after a brief illness.

Born in Waltham, Massachusetts, on March 8, 1973, he was the son of John E. Lupo and Kathleen Dwyer.

John was a self-made entrepreneur who spent much of his time traveling throughout New England and the East Coast, making countless friends along the way. He loved Jelly Roll, the Dropkick Murphys, the Boston Bruins, and spending as much time as he could on his Harley-Davidson. He had a unique sense of humor that could always be counted on to put a smile on someone's face. He was fiercely devoted to his friends and family and loved them with all his heart.

In addition to his beloved daughter, Rhiannon Lupo, he is survived by his sons, Maximus Lupo and Dominik Lupo; his grandchildren, Zaydian Mejia, Zilayais Spaulding, Marlo Spaulding, and Oliver Jones Lupo; his sisters, Kerianne Dwyer, Kathleen M. Dwyer, and Rochelle Hennessey; numerous aunts and uncles; his beloved niece, Teagan Stewart; and his best friends, Shayne Benning, Joshua Hickman, and Emma Simmoneau, who were family in every sense of the word.

He was predeceased by his stepfather, Neal Dwyer; his uncle, Daniel Young; and his aunts, Judy Avron and Mary Beth Lupo.

A graveside service will be held on May 9th at 11 a.m. at Pine Grove Cemetery, located on Patriots Road in Templeton, Massachusetts 01468. The cemetery entrance is on Patriots Road directly across from Sandy Pine Road. A Celebration of Life will follow from 2 to 7 p.m. at the American Legion Post #193, 295 School Street, Winchendon, Massachusetts 01475.

Donations in his memory may be made to a fund established for his children and may be sent to his mother, Kathy, via Venmo @IrishHuntress-2 or Cash App $kathydwyer5.

Arrangements are under the direction of John J. Ferry & Sons Funeral Home, 88 East Main Street, Meriden, CT 06450.