Robert J. Chester

Robert J. Chester died peacefully in his sleep after a short illness on Nov. 20, 2025, at the age of 92.

Born May 24, 1933, as the youngest of seven children, “Bob” spent his early years in Brooklyn. He served in the U.S. Army during the Korean War. After his marriage in 1957, he became a fixture in Carle Place for 30 years, where he enjoyed a robust social life among his many close friends with dinner parties, vacations, golf, fishing on the North Fork and weekday “liar’s poker” lunches at the Cherry Lane restaurant.

He was president of the American Legion, Kiwanis, Chamber of Commerce and Carle Place school board. He received an award from the fire department after rescuing a local family during an active fire in 1965.

After a career in insurance sales, he spent his retirement years in Cutchogue, moving to Riverhead after the death of his beloved wife, Wanda, in 2012.

Bob was known for his wit, sense of humor, love of cigars and Black Russians. He had a happy and positive outlook on life and cracked jokes until the very end.

Deeply mourned by his three children: Diane (Carmine) Arpaia, Christine (Glenn) Dawson, and Robert Chester; and six grandchildren: Carmine (Stephanie), Mark, and Michael Arpaia, as well as Sophie Dawson, Alice (Denis) Brown, and Sarah (Sam) Lawrence; plus three great grandchildren: Abigail, Eden and Leah.

Visitation services will be held at Tuthill-Mangano Funeral Home at 406 E. Main St. in Riverhead, on Sunday, Nov. 23, 2025 from 3 to 6 p.m. The  funeral mass will be Monday, Nov. 24, at 10 a.m. at St. Isidore R.C. Church in Riverhead. A private burial will follow at Calverton National Cemetery.

Memorial donations to East End Disability Associates are appreciated.

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