KENT, Conn.—Robert “Bobby” Clayton Smith died on Saturday, May 16, 2026 after his courageous battle with cancer came to an end at the home of his cousin, Tonya and Daniel Soule, in Kent.
Born on Sept. 2, 1956, in Sharon, he was the son of the late Eleanor Hart Smith and James Smith. Bob’s family resided in Sharon before purchasing and moving to the Bog Hollow Inn in Wassaic, N.Y., where he was a stellar bartender.
He graduated Housatonic Valley Regional High School Class of 1974 and served in the United States Navy. Bob worked at Tri Wall Container Co. in Wassaic, NY, and later as a self-employed painting contractor.
Bob lived life to the fullest. He inherited his love for hunting and fishing from his dad, Big Jim, who surely taught him everything he knew. With his Dad he built a camp in Danforth, Maine, that while being a time-consuming experience, was enjoyed and cherished by the entire family. He also enjoyed bowling, golf, horseshoes, all card games and was a serious and crafty dart player, affectionately named, “Bull’s Eye Bob.”
Bob enjoyed days on the softball field and played in various leagues. He had an unmistakable presence that made him a familiar face both on the field and around town. He affectionately bragged that he could kick anyone’s “butt,”—especially to his four nephews.
Even during his illness, Bob continued to enjoy gathering and socializing with friends and family. He watched the Yankees and NY Giants, usually with a Bob “opinion included.” He enjoyed watching television shows including the “Price is Right,” “Deal or No Deal,” “Jeopardy,” and the Grit TV network and was a frequent Keno and 13-21 lottery game winner.
Bob is survived by his brother, Bucky Calabro, of Poughkeepsie, N.Y.; uncle, Ralph Hart, and his wife, Dixie, of Melbourne, Fla.; aunt, Josephine Cullen, of Orlando, Fla.; brother-in-law, Bruce Osolin, of Goshen; and four nephews, Jamie and Jared Smith, and Kyle and Andrew Osolin; and numerous cousins.
He is also survived by his companion of 12 years, Kerry Coelho, who brought adventures, compassion, understanding, friendship and time together that never wavered. The family wishes to thank Kerry for the selfless love and support she brought to Bob’s life.
Besides his parents, he was predeceased by his sister, Rhonda Osolin and two brothers, Donald Smith and James “Gigi” Smith.
The family and friends extend special thanks to Danny and Toni Soule for all the comforts, support and love they gave Bob in the last year. He was quite happy and content in his surroundings and a place he called “home.”
Calling hours will be held from 11 a.m. to 1 p.m. on Friday, June 19, 2026, at Hufcut Funeral Home, 3159 Route 22, Dover Plains, NY. Funeral services will follow at 1 p.m. at the funeral home. Burial will take place at Valley View Cemetery in Dover Plains, NY.
Memorial contributions may be made to the Kent Volunteer Fire Department, P.O. Box 355, Kent, CT 06757 or online at https://www.kentfire.org/. To send the family an online condolence, please visit www.hufcutfuneralhome.com.