John A. Cunningham

TOPSFIELD - Devoted father and grandfather, John A. Cunningham died on Tuesday June 20th, 2023 at his home in Topsfield, Massachusetts.

John was born on April 20th, 1948 to the late Thomas and Mary (Troyanovich) Cunningham in Peekskill, N.Y. He graduated from Peekskill High School in 1966 and SUNY Cortland in 1970 with a BS in Education. John also counted himself lucky that he was an attendee at the original Woodstock music festival in August 1969 in Bethel, NY. He lived and worked for years in Lake Placid, including managing staff during the 1980 Winter Olympics there. Upon moving to the Boston Area in 1985 John was a valued executive at Positions Incorporated for over 20 years until his retirement in 2009. Following his retirement, he worked part time and contributed greatly to the success of the Staples Copy Center in Danvers, MA. He was well known for exemplary customer service and strong work ethic. John was also instrumental in organizing his Peekskill High School 50th reunion for the class of 1966, working closely with the city’s historian.

John’s greatest joys were his children and grandchildren. He is survived by his treasured children Meghan D. Cunningham of Kihei, Hawaii and Dane (Carolynn) J. Cunningham of Bonita Springs, Florida. John will also be fondly remembered by his three cherished grandchildren Dahlia Katrine Tymoff and Ananias John & Rose Mary Cunningham.

He also leaves behind two brothers Thomas (Susan) Cunningham of Delmar, NY and Michael (Kathleen) Cunningham of Cicero, NY, along with his beloved niece and four nephews. He will be remembered and missed by his brothers for his wit, love of Peekskill, the Hudson River Valley, and the Adirondacks.

In the summers of his youth John spent time vacationing with his family in Wilmington, NY in the greater Lake Placid Region. He continued to return to the mountains for many years, vacationing with his own family, and enjoying the natural beauty of the Adirondack Region. John was also an unwavering fan of the Boston Celtics and a devoted gardener whose work will continue to be enjoyed by the residents of Littlebrook Village in Topsfield, Massachusetts for years to come.

Meghan will honor her father’s memory with frequent trips with her daughter to Ulua Beach aka “Grampy Beach” of Wailea, Hawaii, as will Dane by taking his young son everywhere with him, just as John did with him.

ARRANGEMENTS: Relatives and friends are invited to attend a Celebration of John’s life which will be held at the Holiday Inn & Suites, 2 John Walsh Blvd, Peekskill NY 10566 on Saturday, August 19th from 10 A.M. to 12 NOON. All are welcome. In lieu of flowers, donations can be made to the Peekskill Museum, 124 Union Ave, Peekskill NY, 10566. Assisting the family with the arrangements is O’Donnell Cremations – Funerals – Celebration, 167 Maple St., (Rte. 62) DANVERS. To share a memory or offer a condolence, please visit www.odonnellfuneralservice.com. 

To send flowers to the family or plant a tree in memory of John A. Cunningham, please visit our floral store.