Celebrate Holliston will host annual tradition one final time Nov. 28

The holiday spirit will return to downtown Holliston on Saturday, Nov. 28, as the Holliston Holiday Stroll celebrates its 20th year with trolley rides, local shopping, family activities and the annual tree lighting at Blair Square.

Organized by Celebrate Holliston, the free community event will run from 12-5 p.m., connecting several destinations throughout town and giving residents and visitors an opportunity to discover local businesses and kick off the winter season together. 

The milestone year will also mark the final Holiday Stroll managed by Celebrate Holliston, as the organization prepares to pass responsibility for the cherished community event to new leadership.

The decision comes after years of volunteer effort to keep the tradition alive. Thanks to downtown business owners including John Paltrineri, Donna Cady, and Diane Marrazzo, the tradition continued when the Holiday Stroll faced an uncertain future following the COVID-19 pandemic.

With the town preparing to celebrate its 300th anniversary in 2024, Celebrate Holliston took on the Stroll as part of the broader effort to bring the community together and preserve local traditions. According to Celebrate Holliston President Gina Stucchi, the organization subsequently voted each year on whether to continue managing the event.

According to Stucchi, following the town’s tricentennial celebration, a number of longtime Celebrate Holliston board members completed their terms and stepped away, leaving fewer people to handle the work involved in planning the Holiday Stroll.

“People really wanted to be part of the history, but last year we were desperate for volunteers,” she said, describing the challenges of sustaining the event with a small group of dedicated volunteers.

Although Celebrate Holliston’s leadership is preparing to step aside from managing the event, the organization hopes the tradition will continue under new leadership. For now, organizers are concentrating on delivering a successful 20th anniversary celebration without adding unnecessary complexity to the event. To make planning more manageable for the small group coordinating this year’s festivities, organizers are keeping the overall format simple, focusing on familiar attractions that have helped make the Stroll a beloved Holliston tradition for generations. 

Two vintage-style trolleys, Holly the Trolley and Ellie the Trolley, are expected to return, including one vehicle that is ADA-compliant. The transportation system allows visitors to move between participating locations without having to drive or walk between popular destinations.

A returning destination this year is Willow Brook Farm, where visitors can enjoy food trucks and possibly an animal encounter for children. Attendees will need to take a trolley or walk to the farm, as parking is unavailable.

The Holiday Market at Town Hall and activities at Mt. Hollis will provide additional opportunities for shopping and entertainment. Children, teens and adults will be able to participate in pie-eating contests at Mt. Hollis Lodge, while the Holliston Cultural Council plans to offer crafts and other activities. Additional crafts are typically available at participating downtown businesses where visitors will also find handmade gifts, seasonal treats, and specialty products.

This year’s Holiday Market at Upper Town Hall will again feature independent vendors selling crafts, food, gifts and specialty products. It will also feature entertainment, with Irish step dancing among the planned performances. 

Organizers are also encouraging visitors to watch the event schedule for information about Santa’s appearances. Rather than a traditional photo line, Santa is expected to make several stops throughout the day and participate in a book-reading activity. 

The popular Snowy the Snowman scavenger hunt will also return. Participants will be able to pick up game boards at the Holiday Market and search for Snowy in local shops, giving families an additional reason to explore participating businesses.

Holliston’s picturesque downtown will provide a charming backdrop as Holliston’s community theater group, the Washington Street Players, bring Charles Dickens’ “A Christmas Carol” to life with costumed characters entertaining visitors.

Visitors should consult the official schedule for the latest information about planned activities, performances and locations.

The Holliston Lions Club also plays a key role in the event by organizing the annual tree lighting and securing sponsorships for the downtown holiday lighting throughout the season. 

This year’s tree-lighting festivities at Blair Square will begin at 4 p.m., with the tree lighting scheduled for 4:30 p.m. The program traditionally features local musical performances and seasonal songs, bringing residents together to mark the start of the holiday season.

The tree lighting serves as a fitting conclusion to an afternoon of shopping, trolley rides and family activities, reinforcing the community connections that have sustained the Stroll over the decades.

As Celebrate Holliston prepares to manage the Holiday Stroll for the final time, questions remain about who will take responsibility for organizing the Stroll in future years. More than a shopping event, the Holiday Stroll brings the community together, strengthens connections among neighbors and businesses, and creates lasting memories. 

Visitors should check Celebrate Holliston’s website, www.celebrateholliston.com for the most up-to-date information including the event map, trolley information and updated schedule.