Dolores Anna Bailey

Dolores Anna Bailey, a radiant spirit whose kindness embraced all fortunate enough to know her, passed away peacefully on February 9, 2025, in Holden, Massachusetts. Born on September 8, 1930, in the quaint town of Pittsfield, Massachusetts, Dolores was a beacon of warmth and humor throughout her life.

As a devoted homemaker, Dolores dedicated herself to nurturing her five children. Showcasing a remarkable talent for culinary arts that became her true passion. Her kitchen was not just a space for cooking, but a gathering place where family and friends rejoiced in lavish feasts, each dish a testament to her unwavering love. She skillfully blended the roles of mother and caregiver with her zest for life, ensuring that the hearth remained a place of comfort and joy.

In pursuit of her dreams, Dolores ventured into the realm of professional hairdressing, later establishing a salon within her home. This decision was emblematic of her character—she relished the company of her family and community, intertwining her professional aspirations with her deep-seated love for those around her. The salon became a sanctuary not only for beauty but also for community engagement, where laughter and camaraderie flourished.

Dolores's passions extended beyond the kitchen. She was an avid Bridge player, known for her sharp wit and adeptness at the card table. For years, she hosted weekly gatherings, inviting friends to partake in both the game and the lively banter that accompanied it, a testament to her ability to create lasting bonds through shared experiences.

She is mourned by her five devoted children, Scott, Todd, and Wayne Bailey, and two sisters, Jody Dicroce and Jill Barack, who carry forward her legacy of love and kindness. Additionally, Dolores was blessed with numerous grandchildren and great-grandchildren, whose lives will be forever touched by her nurturing presence and infectious laughter.

Dolores Anna Bailey was predeceased by her beloved husband, Willard Bailey (Woody), her mother, Mary Pivero, and her brother, Ralph Pivero. Together, they leave an enduring imprint on the hearts of all who knew them.

In celebrating her life, we remember Dolores as a vibrant soul whose spirit illuminated the lives of many. Her kindness, humor, and culinary delights will forever be cherished by her family and friends, echoing in the laughter and love shared around the tables she so lovingly prepared.

A celebration of her life will be announced in late spring.