Gay Annette Sherman Weintz of Essex, CT, left this earth on April 22nd, 2024. She was 55
years old.
Gay was a brilliant woman with renaissance passions and skills, a whimsical way in her life and
expression, and someone who sought joy and embraced it as it came. Born on July 17, 1968, in Warwick, RI, Gay grew up in Deep River, CT.
She was a graduate of Valley Regional High School and Boston University, going on to earn a Master’s in Education
from Lesley University.
Throughout her life, Gay had a strong sense of determination and constant desire to learn and
try new things. After one college semester at the University of Padua, she returned home
speaking fluent Italian. Professionally, she was always ready to take on a new challenge - she
worked on the Spirit of Massachusetts schooner out of Boston Harbor, served as a transplant
coordinator at Boston Children’s Hospital for a world-renowned liver transplant surgeon, and an
Italian translator at Boston’s Logan Airport; she taught 5th and 6th grade in Martha’s Vineyard
and Pensacola, FL, and developed award-winning curriculum for Gannett’s Newspapers in
Education. She pursued excellence in everything she did.
Gay was also a vintage jewelry expert, appraiser and historian who ran a successful online
store, Vintage Under the Sea for over 10 years, attending auctions, antique fairs and appearing
on shows including “If This Brooch Could Talk” on iCRV Radio to share her knowledge. Her
pieces were worn on several seasons of the period series “Mad Men” set in the 1960s and by celebrities.
Gay also curated a large and stunning collection of Christmas tree pins, her
favorite type of brooch. Behind every piece was a story—a story that Gay was fascinated to
learn while helping others feel a little more beautiful and confident.
She loved music, reading, travel, spending time outdoors and time with her son. Gay’s true
heart lay with the ocean. Whether she was sailing, swimming, boating, or taking a walk on her
namesake beach at Gay Head (Aquinnah) on Martha’s Vineyard, the water was her happy
place. She was also a beautiful storyteller and writer, lending her unique voice to poems, short
stories, and song lyrics.
A long-time resident of the Tri-Town area, Gay was a kind friend and loving supporter of the
community. In high school, she made prom dresses for a few of her classmates, barely finishing
her own in time. Many of Gay’s friends spoke of her wicked sense of humor and constant
willingness to offer help and support to anyone facing hard times. Gay was honored to be a
member of the “Ivoryton Witches,” performing the Witches Dance every year at the Ivoryton
Village Pumpkin Festival and had much fun marching her pet pig Hershey in the town’s 4th of
July parade.
Gay’s greatest accomplishment is her 19-year-old son, Chauncey. She was a Mom first and
foremost and always made him her priority. This shows in Chauncey’s character, and Gay will
continue to be there for him via her family, her extended family of friends, and those she
supported in a myriad of ways in her life. Her joyful laugh and beaming smile will be sorely
missed by all who knew her.
Gay is survived by her beloved son, Chauncey Sherman Smith, sister Bethany Durkin and
Robin Sherman-Harper, brothers-in-law Kevin Durkin and James Harper, and nieces Galen,
Olivia, Lucy and Jude. She is predeceased by her mother, Ann Helen Sherman, father Richard
Anthony Sherman, and brother Richard Mark Sherman.
A Celebration of Gay’s life will be held at Deep River Congregational Church on May 18th at
2 p.m., followed by light refreshments and fellowship in the Parish Hall. The service will be
livestreamed at https://deeprivercc.org/livestream/. In lieu of flowers, you may donate to a
GoFundMe established to help support Gay’s son; details can be found on her Facebook page, facebook.com/gaysherman.
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