By Judith Dorato O’Gara

 For the second year in a row, Celebrate Holliston is presenting Holliston’s Annual Holiday Stroll - A Small Business Saturday celebration, taking place for the 19th year, on Saturday November 29, 2025, from 12 to 6 p.m.!  Visit Celebrate Holliston’s Holiday Stroll page for details: https://www.celebrateholliston.com/stroll.html.

Gina Stucchi, this year’s president of Celebrate Holliston, explains how Celebrate Holliston came to run the Holliston Holiday Stroll, formerly run by Diane Marrazzo, Donna Cady and John Paltrineri as members of the former Holliston Business Association. 

“For a few years, the Holiday Stroll almost completely went away,” says Stucchi, who explains Karla Alfred became involved, eager to build the event up once again. “The year before the 300th, we approached Celebrate Holliston and asked if we can take on the Holiday Stroll, so we took it over last year, for the 300th, and did a big event.” The effort, however, is a big undertaking for Celebrate Holliston, as it comes on the heels of the Celebrate Holliston field day, and it could use volunteers dedicated to it. She likes to think of Celebrate Holliston as the event’s “foster parents.”

“Hopefully, we can find a good place for this, as it should be businesses or an economic development committee, but it’s placed with Celebrate Holliston right now. We’re voting year-to-year to run the event,” she said.

“It’s a lot of work,” says Paltrineri, owner of Fiske’s, adding, “Donna and myself and Diane,

we did it 20+ years, and of course, it’s a tough time of year for us to do it.” Paltrineri explains more volunteers were needed. “Many hands make the work lighter, and all the planning is done months in advance. I think they’re doing a great job.”

Alfred, who’s lived in Holliston since 2011, says she stumbled across the Stroll at one point and loved it. She echoes Stucchi’s sentiment that the turnaround from wrapping up the field day and pivoting to the Stroll is a challenge. 

“It’s a free event for the public, and that’s what makes it magical,” says Alfred, “ and the idea is to highlight Holliston businesses.”

She points out the Holliston Lions, who handle holiday lights for the town, came up with the idea of getting holiday trees to assemble at Blair Square, with different nonprofit groups decorating them. Those trees will be on display at the tree-lighting. 

Many local businesses offer something special for the stroll. Last year, says Alfred, the library and police department held activities, but their participation had yet to be confirmed at press time. What is confirmed is below:

• Trolleys- this year- double decker trolleys will be running from 1-6 p.m. throughout downtown areas -guaranteed stops: Historical Society (12-4), Masons Hall, Blair Square (at least 2 more will be added throughout town)

• Celebrate Holliston’s Chili Contest will take place at Mt. Hollis Masonic Lodge (Masons Hall). Chili-makers must gather ingredients, pots and utensils and prepare 1.5 gallons of their best chili AT the hall, which will be open at 6:30 a.m. The public can sample the chili starting at noon, and the People’s Choice Award will be announced at the tree lighting. Visit https://www.celebrateholliston.com/chili.html .

• The annual tree lighting by Holliston Lions, with help from Holliston Girl Scouts, will be at 4:15 p.m. in Blair Square, where you can find Stroll information and booths by Trolley-level sponsors.

• The Giving Tree and Holiday Trees will be on display in Blair Square.

• A Vendor Market will take place at Holliston Town Hall, 12-4 p.m. (Although November 1st was the deadline to be included in printed materials, vendors will be accepted until November 15th.)

• Santa will be out and about!

• Snowy’s Scavenger Hunt is back for a second year!

The Holiday Stroll web page will continue to be updated as the date approaches. Find information at https://www.celebrateholliston.com/stroll.html and visit Celebrate Holliston on Facebook.