The Friends of Holliston Trails’ First Night Trail Walk will be back on December 31st, after a shortage of volunteers led to last year’s event being canceled. It’s been ten years since the group put on its humble first First Night event and the popularity keeps growing, with as many as 3,000 strollers from Holliston and surrounding towns.  

“The trail has been called the crown jewel of Holliston and this event invites people to explore the trail in a new way,” said FOHT President Gretchen Prieve. “Along the walk there’ll be lights, volunteers staffing fire pits for warmth, entertainment, decorations, and snacks,” she said.

The festivities, which also kick off Holliston’s 300th anniversary, run from 5:00 – 8:00, from Blair Square to Cross Street, with Phipps tunnel as centerpiece of the stroll. Boy Scout Troop 73 will be grilling up hot dogs and handing out hot chocolate in the tunnel. Young families often start at Cross Street to make the walk shorter; it’s about a mile from Blair Square.

The Unlikely Strummers, a community-based group of ukulele players, will be back this year, along with a lot more entertainment. 

“In Blair Square we are adding a DJ this year,” Prieve said. “And Erosbooth will bring energy to Blair Square like we’ve never seen with music, lights, and a 3D photo booth. Three Ring Creations is also new to Holliston this year with an LED juggling act to dazzle our youngest walkers.”

In addition to the entertainment, one of the biggest draws of the Trail Walk is to see how friends and neighbors do up their fire pits. Liz Woodhouse and her husband Eric (Slick) Woodhouse generally set up a fire pit and a tent with all sorts of baked goods, holiday cookies, hot chocolate and cider.

“We like to create a little family-friendly spot that parents and kids can enjoy as they mosey down to the tunnel,” Woodhouse said. “The holidays are so busy for everyone, but this event allows us to slow down and see some of our friends and neighbors. The rail trail provides so much to the community; it’s one of the reasons we moved here,” Woodhouse said.

Anyone can sign up to host a fire pit. Woodhouse said it’s a great way to get to know people in town.

The fire pits are also a great way for Holliston’s organizations and businesses to showcase what they do for the town. Master electrician Jon Sutherland owns JSE Corp. and lives along the trail. He sets up behind his house, between Exchange and Arch Streets.

“Not to be too competitive, but I run the best fire pit every year,” Sutherland said. “We have two fires going, including a barrel fire and a small grill. And we typically have about 30 people waiting to roast marshmallows for s’mores. This year I’m considering setting up a big top tent. I love doing it and look forward to it every year.”

You can also find pits hosted by Ed and Dorianne Daniels, owners of Vesta Real
Estate Group; Bob Savin, who owns Fitness Together gyms in Ashland and Southborough; and Mike Carvalho, who’s working to create a bike park in Holliston. Middlesex Savings Bank isn’t hosting a fire pit, but this year the bank provided a grant that’s helping to fund entertainment. “This is Holliston at its best. It’s a family-friendly, fun way to celebrate New Year’s Eve. Whether a participant walks the entire length of our event or just a short portion, they’ll experience the trail in a unique way,” said FOHT’s Prieve. Parking for First Night is available in the Blair Square parking lot, the Exchange Street municipal lot, Robert Adams Middle School, Placentino Elementary School and at Cross Street. Many local businesses (CVS, Depot Package Store, Casey’s, etc.) will be open for business on December 31 during the event, so the FOHT asks that you not park in their lots.