John Woodruff

St. Petersburg - John Woodruff (November 23, 1941- July 5, 2025) was an artist, a father, a veteran, and a mean tennis & racquet ball player. But he can best be described as a free spirit who often said his "wanderlust" was the force that kept him exploring new places, meeting new people and making friends everywhere he went. He spent most of his life as a portrait artist and whether his subject was a famous celebrity or a stranger on the street, he treated them all with the same friendly charm.

John was born in Syracuse, New York to Henry & Jane Woodruff. He was the middle child between older brother Sherman and younger brother Jason. They grew up in Nutley, New Jersey which is where John first discovered his great passion for art.

John graduated from Nutley High School and attended Syracuse University before joining the Marines in Paris Island, North Carolina.

After the Marines, John grabbed his easel and brushes and set up shop on Atlantic Beach, North Carolina where his life changed forever.

It was on Atlantic Beach where John met his first wife Jyoti Parry and they soon had twin boys, Jase & Jon. They headed back North to be near family and it was there that John really honed his artistic craft.

John started painting portraits on Bleeker Street in New York City in the late 1960s at a time when the street was filled with artists, poets and musicians who had come to New York City to chase their artistic dreams. Jyoti remembers- "It was on Bleeker Street where John really learned so much from other talented artists and became a great artist himself."

John's "wander lust" took him to many new places throughout the years, but in the 1990s he settled down in Mashpee, Mass when he married Amy Rice and they had a daughter, Amber.

John and Amy founded Woodruff's Art Center in Mashpee and Amy describes John as a local legend. Amy remembers- "John was a mentor to everyone. He taught art to adults and gave free lessons to kids. He let the kids paint the walls and even his van! Everyone loved him."

John spent much of his later years living on Maui where his son, Jon, also lived. He was a fixture painting portraits on the streets of the surfer town Paia and at Charley's Bar there.

After a move to Florida, John's health got in the way of his painting and racquet ball. He still kept his positive outlook though until the very end. He died peacefully surrounded by love.

We can only imagine Jonn is still sitting behind his easel with brushes (and maybe a Mike's Harder Lemonade) waiting for his next subject. Paint on, John! Paint on!