On Saturday, November 28, Holliston holds its 20th Holiday Stroll. The free event runs from noon to 5 p.m. Trolleys will run between the farm, downtown, Town Hall and Mt. Hollis, and the afternoon ends with the Lions Club tree lighting at Blair Square. It will also be the last Stroll run by Celebrate Holliston, the volunteer group that has organized it since the town's tricentennial.
The Stroll has changed hands before, and each time a different group of people kept it alive. This year's tree lighting takes place in a square that Celebrate Holliston helped pay to rebuild. So the group's final Stroll also shows off one of the larger things it gave the town.
Why this is Celebrate Holliston's final year
Holliston Local Town Pages reported in late October that Celebrate Holliston took on the Stroll as part of its push to bring people together ahead of the town's 300th anniversary in 2024. According to Celebrate Holliston President Gina Stucchi, the board voted every year after that on whether to keep running it. After the tricentennial, Stucchi told the paper, several longtime board members finished their terms and stepped away, which left fewer people to do the planning.
"People really wanted to be part of the history, but last year we were desperate for volunteers."
That is how Stucchi put it to Local Town Pages. The same article says that with a small crew handling the 20th, organizers are keeping things simple and sticking to the attractions people already know. The group hopes someone new will take the Stroll on, but who will run it in 2027 is still an open question.
The last time it nearly stopped, shop owners restarted it
The Stroll has been through this before. Local Town Pages credits downtown business owners John Paltrineri, Donna Cady and Diane Marrazzo with keeping it going when its future looked uncertain after the COVID-19 pandemic.
In November 2023, the Holliston Reporter covered the comeback. "It's time," Paltrineri told the paper. He had recruited fellow volunteers Karla Alfred, Steve Apesos and John Drohan to help. That year he lined up 20 businesses for Small Business Saturday, and each one set out donation jars for the Community Action Fund and the food pantry. At 4 p.m., carolers gathered in front of Fiske's and walked to Town Hall for the tree lighting.
That 2023 lighting at Town Hall broke with tradition, according to the Reporter. In earlier years, the lighting had been at Blair Square, around a tree donated by Rep. Carolyn Dykema, and the renovation of the square had taken that tree out. This year the lighting is back at Blair Square, and the square it returns to was rebuilt with help from the group now stepping aside.
The square Celebrate Holliston helped build
A town-appointed Blair Square Committee was asked to redesign the space with two goals in mind: fix drainage, and create a safe gathering place that could serve many uses. Town Meeting approved Community Preservation money for the project in May 2022. The designers' account in Landscape Architect says the project was built with CPA and ARPA funds and finished just before Memorial Day 2023.
Private donations went toward the pavilion. Friends of Holliston Trails began a $45,000 matching campaign in May 2022. In January 2023, Celebrate Holliston announced it would match that with $45,000 of its own, for a combined $90,000 toward the pavilion. Peter Barbieri, a Celebrate Holliston board member, told the Reporter at the time that the group expected Blair Square to "become a focal point for the Town activities."
The town's project narrative spells out what the redesign planned:
- the rail trail moved west to keep cyclists apart from the gathering areas
- an event lawn and a permeable-paver plaza
- a covered pavilion
- Milford Pink granite seating, benches and a bubbler
- new trees, shrubs and planting beds, plus wayfinding signs
Holliston Cable Access Television filmed a ribbon cutting at the square on October 22, 2023. That was the same fall Paltrineri's volunteers brought the Stroll back.
The afternoon, stop by stop
Two vintage-style trolleys, Holly and Ellie, connect the stops, and one of them is ADA-compliant. The official Stroll page lists five stops.
| Trolley stop | What's planned for 2026 |
|---|---|
| Willow Brook Farm | Food trucks and possibly an animal encounter for kids. The farm has no parking, so walk or take the trolley. |
| Downtown Holliston | Participating shops with handmade gifts, seasonal treats and crafts, plus the Snowy the Snowman scavenger hunt |
| Holliston Historical Society | A listed trolley stop on the route |
| Holiday Market at Town Hall and Mt. Hollis | Independent vendors and Irish step dancing at Upper Town Hall. Pie-eating contests for kids, teens and adults at Mt. Hollis Lodge, plus crafts from the Holliston Cultural Council. |
| Jack's Auto | The drop-off for the Blair Square festivities |
The Upper Town Hall market is set up for local businesses and makers who don't have a storefront on the trolley route. Pick up a Snowy game board at the market, then look for the snowman in local shops. There won't be a traditional photo line with Santa. Instead, he's expected to make several stops during the day and take part in a book reading. The Washington Street Players, Holliston's community theater group, will be downtown in costume as characters from Charles Dickens' "A Christmas Carol," which the MetroWest Boston Visitors Bureau's holiday events roundup calls "Stroll with Scrooge."
Shops come up with their own touches, too. A photo from last year's Stroll shows a "Holiday Labubu" greeting visitors at Purely You Spa.
How the day winds down at Blair Square
The Holliston Lions Club runs the tree lighting. The club also lines up sponsors for the downtown holiday lights that stay up through the season. Here is how the afternoon ends:
- Noon to 5 p.m.: trolleys, shops, the market and Mt. Hollis activities
- 4 p.m.: tree-lighting festivities start at Blair Square, usually with local musicians and seasonal songs
- 4:30 p.m.: the tree is lit
Trolley timing, the event map and any schedule changes will be posted on celebrateholliston.com, and organizers ask visitors to check there for the latest. If the experience of the last few years holds, whether there's a 21st Stroll depends on who reaches out to Celebrate Holliston before next fall. The group's contact page and its email, [email protected], are listed on that same site.
Our team loves the Saturday after Thanksgiving in Holliston, when shop owners, volunteers and neighbors all fill the same few blocks. If your family is also thinking about a move in 2027, Darlene & Company can work out the timing of a sale and a purchase so you can still make it to the next Stroll. Get your free home valuation and move plan.
