Judy Rosley, 86, of Sheffield

Judith Carol Rosley, the daughter of Sylvia Friedman and Jack Shapiro, passed away peacefully in her sleep Saturday, April 27, surrounded in her final days by the love and embrace of her friends and family. Quick-witted, playful, resourceful, kind and impossibly full-hearted, she was deeply loved and admired by those close to her.

Judy Rosley

Born amidst the Great Depression and growing up in Woodmere, New York, she was a proud big sister to her younger brother Joel, who she gleefully taught to play and love sports including tennis, baseball, yoga and bicycling. A beautiful fashionista and an artist, she cultivated and emanated style throughout her life as a designer, an antique dealer, a healer, a poet, a writer, a therapist, a dancer and a radio host. She married Hal Schwartz in 1955 and raised two brilliant children, Jill and Jonathan, who she exposed the world to through travel, culture, passion, understanding and an appreciation for art. She encouraged her children to be big dreamers and find joy in their lives.

She was always ahead of her time: an unabashed gift-giver; a scribe of long, illegible love notes; a generous soul; the life of the party; a lifelong learner; a student of the spirit; a host of fashion shows and themed parties; and a collector of silver linings. She was a deep conversationalist, an inquisitive interlocutor and a remarkable listener.

Judy later married Walter Rosley before welcoming two precious joys of hers, her grandsons Wyatt and Cooper. Her quest to spend quality time around them brought her from Manchester, Vermont, to Sheffield, Massachusetts, where she spent the last 15 years of her life. She spent long spring afternoons in lawn chairs watching her grandson Wyatt play baseball and lazy weekends on the couch reading poetry with her grandson Cooper. She indulged her grandsons’ interests, taking them on solo trips to explore their passions.

She marched to the beat of her own drum, but she leaves behind an army of likeminded loved ones including her brother Joel; her children Jill and Jonathan; her grandsons Wyatt and Cooper; and her adorers Hal, Nan, Ron, Steve, Doreen, Ruth and Ellie. She will be indescribably missed, but Judy Rosley’s legacy will live on for generations because of the impact she had on those around her with every ounce of her life and love.

A memorial service will be held Wednesday, May 1, at 3 p.m. at Congregation Ahavath Sholom, 15 North St., Great Barrington, MA 01230. All are welcome. In lieu of flowers, please send donations to the Parkinsons Foundation c/o FINNERTY & STEVENS FUNERAL HOME, 426 Main St., Great Barrington, MA 01230, which is caring for the arrangements. To send remembrances to the family, go to www.finnertyandstevens.com.