Holliston's 20th Holiday Stroll Is Celebrate Holliston's Last. Here's the Route, Stop by Stop

"People really wanted to be part of the history, but last year we were desperate for volunteers." That is Celebrate Holliston President Gina Stucchi, speaking to Holliston Town News about the town's Holiday Stroll. On Saturday, Nov. 28, the Stroll turns 20, and it will be the last one Celebrate Holliston manages.

The event is free and runs from 12 to 5 p.m. It ends with the annual tree lighting at Blair Square. Each piece of the afternoon belongs to someone else. A riding farm hosts the food trucks. Shoppers browse vendor tables in Town Hall. The pie-eating contests happen at a Masonic lodge. A historical society opens a Federal-era house, and the Lions Club lights the tree. Celebrate Holliston's real job has been to join all of that into a single route, and that is the job looking for a new owner in 2027.

How the Stroll Reached Year Twenty

The Stroll nearly ended once already. According to Holliston Town News, downtown business owners John Paltrineri, Donna Cady and Diane Marrazzo kept it going when its future was uncertain after the COVID-19 pandemic.

Celebrate Holliston took it over during the run-up to the town's 300th anniversary in 2024. The paper reports that the group's board voted each year on whether to keep managing it. After the tricentennial, several longtime board members finished their terms and stepped away, which left fewer people to do the planning.

To keep year twenty manageable for a small crew, organizers are holding the format steady and sticking with the attractions people already know. The group hopes someone new will pick the tradition up for future years.

The Route, Read as Washington Street Addresses

The Celebrate Holliston Stroll page lists five trolley stops: Willow Brook Farm, the Holliston Historical Society, the Holiday Market at Town Hall and Mt. Hollis, downtown Holliston, and Blair Square. The Holiday Market stop takes in two buildings, Town Hall and Mt. Hollis Lodge, and the last two stops sit together in the center. Ordered by street number from highest to lowest, the places behind those five stops mark out the stretch of Washington Street the trolleys cover.

1. Willow Brook Farm, 1070 Washington Street. This is an equestrian facility with riding lessons, summer camps, an IEA riding team and therapeutic riding. Its website lists more than 30 lesson horses, indoor and outdoor arenas, and trail access. On Stroll day the farm hosts food trucks and possibly an animal encounter for children. There is no parking there, so you need to take a trolley or walk.
2. Holliston Town Hall, 703 Washington Street. Upper Town Hall holds the Holiday Market again this year. Independent vendors will sell crafts, food, gifts and specialty products, and Irish step dancing is among the planned performances.
3. Mount Hollis Lodge, 657 Washington Street. Mt. Hollis is a Masonic lodge, A.F. & A.M., and its first communication was held on March 6, 1865. It hosts the pie-eating contests for children, teens and adults, and the Holliston Cultural Council plans crafts and other activities there.
4. Holliston Historical Society, 547 Washington Street. The Historical Society is based at the Asa Whiting House. Colonel Asa Whiting built the Georgian Federal house around 1812, close to the road. It was moved back to where it stands now in the early 1930s. The barn dates to 1817, and the Society bought the house and barn in 1967.
5. Downtown and Blair Square. Downtown is where the shops come in, and it is where the afternoon ends.

Town Hall and the lodge are 46 numbers apart and work as one stop. The farm at 1070 and the Historical Society at 547 sit at opposite ends of the route. Two vintage-style trolleys, Holly the Trolley and Ellie the Trolley, are expected back, and one of them is ADA-compliant. They are what lets a family see the horses, the market and the tree lighting in one afternoon without moving the car.

Downtown Has Its Own Game Board

Downtown has the loosest structure of any stop, and also the most moving parts. The Snowy the Snowman scavenger hunt is back. You pick up a game board at the Holiday Market and then look for Snowy in local shops. On the organizer's page, the hunt is an add-on for brick-and-mortar businesses, capped at 12 locations. The same page sells vendor booths in Upper Town Hall and listings or ads on the event map. So the Stroll's own sign-up forms connect a market in a civic building to a dozen storefronts down the street.

Participating downtown businesses usually offer more crafts, plus handmade gifts, seasonal treats and specialty products. Last year, according to a Celebrate Holliston photo in Holliston Town News, a "Holiday Labubu" greeted visitors at Purely You Spa.

The Washington Street Players, Holliston's community theater group, will be downtown again in costume as characters from Charles Dickens' "A Christmas Carol." Santa will make several stops during the day and take part in a book reading instead of sitting for a photo line, so his appearances are listed in the event schedule.

Blair Square Belongs to the Lions

The last stop has its own organizer. The Holliston Lions Club runs the tree lighting and lines up sponsors for downtown's holiday lights all season. The Blair Square program starts at 4 p.m. and the tree is lit at 4:30. Local musicians and seasonal songs are part of the program by tradition.

That timing shapes the afternoon. The Stroll officially ends at 5, so the tree lighting falls inside the last hour, and anyone at the farm at 1070 Washington Street needs a trolley back toward the center in time. Celebrate Holliston will post the final schedule, trolley details and event map at celebrateholliston.com.

The Same Volunteer Groups, Before and After Nov. 28

The Stroll is the most visible event on Holliston's late-fall calendar, but most of the groups behind it have events of their own on either side of it.

The Holliston Historical Society is running its second annual Holiday Door Décor Contest. Holliston residents can submit photos of their decorated doors through Dec. 13, and winners will be announced Dec. 18, as Holliston Town News reported.

Holliston Newcomers & Neighbors is collecting Thanksgiving cards to go out with senior meal deliveries. The deadline is Sunday, Nov. 15, and cards can be dropped off at 922 Highland St., the Holliston Reporter reported.

Holliston Public Library at 752 Washington St. has a run of events on its calendar:

The Veterans Appreciation Coffee is on Thursday, Nov. 12, the day this post goes up. At 752, the library is on the same Washington Street corridor as the trolleys, between Town Hall and Willow Brook Farm.

In August we wrote about how the rail trail became Holliston's evening Main Street. The Holiday Stroll does something similar for one Saturday a year on Washington Street, and after Nov. 28 Celebrate Holliston will no longer be the group running it. You can find more about the town on our Holliston neighborhood page.

Steve Leavey has worked in Holliston and the surrounding MetroWest towns for many years, and part of knowing this market is knowing which streets, farms and civic buildings hold the town's traditions together. If you are thinking about what your home on or near Washington Street is worth, or how a sale might fit around the holiday calendar, Request a Complimentary Market Consultation.