Tom Fletcher was a complicated man, brimming with deep curiosity and a keen sense of humor. His generosity was legendary. He loved babies, toddlers, little kids — he was in his element when hanging out with children. Tom was a highly skilled raconteur; he could tell a story like nobody else, and he was the subject of many outrageous sagas, too.
Tales about Tom could fill an entire book. The world may be a calmer place, but it feels a lot less interesting now that he’s gone. RIP, Tommy.
“Tom was one of the most generous people I’ve ever met,” said his companion, Julia Jordan, “He gave money to the homeless often. Once, during one of our many trips to New York City, we came across a homeless father and son. Tom handed the son money and told him to take his father out to lunch. The boy looked at Tom with such joy and gratitude.
“Tom’s generosity shone through whenever I was with him. One night, we were out listening to Irish music. Tom reached in his pocket to tip the musicians. When he discovered he only had a $100 bill, he went ahead and tossed the hundred into the tip jar. The look of surprise and delight on the faces of the band members was priceless.”
Tom’s legacy looms large in Woodstock. His son David credits his charismatic father for gifting him the people skills and boldness required to open a restaurant, Medo. David hopes to use Tom’s spirit to help grow the community his father loved.
David’s father was always reliably generous in restaurants as well. Whether there were two or ten in the party, Tom would invariably pick up the bill long before anyone else realized it was there.
The Fletcher Gallery opened in 1992. The highly successful gallery featured artists from all over the Hudson Valley. Fletcher Gallery ran for 28 years and was one of the centerpieces of downtown Woodstock.
Tom’s brother Ralph visited him a year or two after Tom opened Fletcher Gallery. He remembered noticing a sense of confidence and optimism in his brother, and mentioned it to him. “I feel like I’ve come into my own,” Tom acknowledged.
Ralph felt that sentiment rang true. “Woodstock was Tom’s true home, a place that — most of the time — brought out the best in him,” Ralph said..
As an art entrepreneur, Tom held exhibitions of many kinds of “Woodstock” art. He had a positive attitude. He genuinely loved new discoveries and long-neglected local talent. He could be depended upon to bring enthusiasm to whatever he did.
In addition to art, Tom was passionate about gardening, nature, the ocean, the night sky, and poetry. He published a book of original poetry, “Falling Through the Earth,” in 1991.
“The day before Tom passed, we took one of our usual walks in the woods,” recalled Julia Jordan, a photographer. “It was a particularly gorgeous day. The setting sun bathed the greens of the leaves, and the moss on the rocks in a warm light. I noticed a small toad and pointed it out to Tom. He picked it up, looked at it, then gave the toad a gentle kiss.
“Of course, this wasn’t the first time I’d seen him do something like this. ‘Tom,’ I asked, ‘why did you kiss that toad?’ As he set it softly down, he replied, ‘Because I love him, he’s so cute.’ And that was the sweet heart of Tom. He will be greatly missed.”
“Live the questions,” the poet Rainer Marie Rilke advised. Tom never stopped living the questions about God, love, the cosmos, the meaning of life, etc. He was always ready to engage in dialogue, occasionally argument, about these iconic matters.
Thomas Fletcher died in Woodstock on September 30, 2023. He was 66. Tom is survived by his son, David Fletcher; his companion, Julia Jordan; former wife Sharon Capra; his siblings: Ralph JoAnn (Portalupi), Jim, Joe (Christine), Elaine Vega (John Novo), Kathy Fletcher (David Simpson), Carolyn Fletcher (David Blue), as well as many adoring nieces and nephews.
Tom’s parents were Ralph and Jean Fletcher. The fourth of nine children, Tom was born in Weymouth, Massachusetts in 1956. In 1975 he graduated from West Islip (NY) High School. When Tom was 17, his brother Bob was killed in a drunk-driving accident, an event that rocked the entire Fletcher family.
For many years Tom struggled with health issues, including alcohol and drug addiction. This would lead to his untimely death.
A celebration of his life will take place at 1 p.m. at the Byrdcliffe Colony, Woodstock, on November 4, Tom’s birthday.
Join the family! 
