The Town of Holliston announced on Mar. 27 that it will hold its first annual History Day on Saturday, May 2, 2026, at Blair Square. The event is intended to celebrate the town’s heritage and highlight the role of the rail trail in Holliston’s development.
According to organizers, History Day aims to foster community spirit by bringing residents together to reflect on Holliston’s past and its continuing evolution. This year’s theme is “Tracks Through Time: The Evolution of the Holliston Rail Trail.”
The celebration will focus on how the railroad has shaped Holliston since its arrival in 1848 and how the current Rail Trail continues to serve as a connection between the town and wider world. Planned activities include guided walking tours led by local experts along the rail trail, interactive exhibits featuring historic artifacts at Blair Square, and opportunities for all ages to engage with local history.
Organizers said they are excited about launching this new tradition for Holliston. “We are thrilled to announce a brand-new tradition,” according to their statement. “Join us this May for our inaugural History Day as we celebrate the rich heritage that makes our community unique.” They also encouraged residents to stay tuned for more details as May approaches.
Further information about specific events and schedules will be provided closer to the date. Community members are invited to gather at Blair Square on May 2 for what organizers hope will become an annual opportunity to connect with both history and neighbors.


