Judi Milano

7/9/1940 – 3/10/2019

 “Heading over to Bradley Palmer to spend a morning riding with my husband or meeting girlfriends to head out on the trail is what I love.”

Judi (Pinto) Milano, 78, of Boxford, beloved wife of Joseph J. Dailey,  passed away March 10, 2019 in her home.

Judi’s love of life revolved around family, horses, art, and music.

For eleven years, she entertained audiences as Cowgirl Judi on the Rex Trailer TV show Boomtown. Judi would handle her trick horse, Goldrush, on-stage, at personal appearances, and in parades. After Boomtown, competitive 100-mile endurance riding became her challenge. Since then, she cultivated a passion for trail and carriage driving, as a member of Essex County Trail Association, Myopia Driving Club, and Green Mountain Horse Association.

A long-time Boxford resident, Judi was always ready to meet friends for a ride at Bradley Palmer State Park. Anyone riding regularly on the trails in and around Bradley Palmer Park knows Judi. She rode the trails daily for more than thirty years, building a knowledge of the complex trail network like few others.  Long-time friend, Sue Knowles, describes her as a trail-riding institution. 

Always interested in challenging herself, Judi decided to hone her talent as a watercolorist, studying with teachers in Marblehead. Her skill, eye for subject matter, and charming aesthetic appealed to many, and she soon was having shows and selling her work. Judi’s artistic abilities transcended generations: Her daughter and granddaughter are both artists, continuing her legacy.

Judi had a lifelong love of music. She fondly remembered her father singing Saint James Infirmary while buttering toast as she and her sister would join in two-part harmony while doing the dishes. Struck by the experience of researching and singing songs of the era for her father while he lay in hospice, Judi formed a singing duo called the Palomino Singers with her neighbor, Carol Johnson. They entertained area senior citizens with nostalgic songs they could relate to. Judi found these experiences to be very rewarding.

Judi leaves behind many horse-lovin’, stall-muckin’, guitar-pickin’, songwritin’, trail-ridin’, dog-walkin’, murder-ballad-singin’, lobster-eatin’, antique-shoppin’, ice-cream-lovin' friends and family who sorely miss her.

In addition to her husband she is survived by a daughter, Lauren Gillette and her husband Timothy Rotman of York, ME; a granddaughter, Isabella Rotman of Chicago; a brother, Stephen Pinto and his wife Donna of Newton; a sister, Susan Faenza and her husband Daniel of Meredith, NH and several nephews and nieces.

Private arrangements are under the direction of the Whittier-Porter Funeral Home of Ipswich. Memorial contributions in her name may be made to the Essex County Trail Association, Box 358, Hamilton, MA 01936.

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