Holliston Holiday Stroll 2025

The Holliston Holiday Stroll is back for 2025! Come join the festivities! We will be listing participating businesses as they join the Stroll.

Snowy the Snowman is back with new hiding places and more prizes!

Santa will be handing out candy canes!

The Celebrate Holliston Chili Contest will be in full swing!

Blair Square will be decorated by the Light Up Holliston committee, complete with our Holiday Dreams tree, town organization trees, performances, Trolley Sponsor tents, and the annual tree lighting at 4:15pm.

Stay tuned for a schedule of events, official Stroll map with participating businesses, and more!

Also check out other Contests in Holliston.