With a tip of the cap to sartorial sophistication and genteel tradition, guests at Jackson Walnut Park School’s (JWPS) upcoming annual spring gala will show off their Kentucky Derby style while raising funds to support the school’s growth.
JWPS, the only institution in the Boston area offering Montessori early childhood education and a Catholic elementary program sponsored by the Sisters of St. Joseph of Boston, will host its “Hats & Hearts” Gala on Saturday, May 2, 2026. The highly anticipated event will bring together families, alumni, and supporters for an evening of celebration, storytelling, and philanthropy in support of the school’s continued growth and impact — all with a touch of Southern sophistication.
Inspired by the elegance and excitement of the Kentucky Derby, guests are encouraged to wear their finest hats, fascinators or bow ties while enjoying delicious cuisine, lively music, and live and silent auctions. Proceeds from the gala will fund key school initiatives, including new playground equipment and outdoor basketball and tennis courts. These improvements will enhance the student experience and support the school's long-term goals.
Highlights from the evening will feature remarks from distinguished alumni who will share reflections on their formative years at JWPS and the enduring influence of its close-knit community and values-based education.
The “Hats & Hearts” Gala underscores Jackson Walnut Park School’s commitment to fostering academic excellence, character development, and a strong sense of belonging. Through shared stories and collective generosity, the evening will celebrate the school’s legacy while helping to shape its future.