GREENFIELD — Building off the longstanding tradition of the tree lighting ceremony and the days when Santa would visit the now-closed Wilson’s Department Store, the Greenfield Business Association (GBA) has been adding to the holiday cheer with its annual Jingle Fest.

This weekend, the event returns for its 11th year, and organizers are getting as many businesses and community members involved as possible, according to GBA Director Hannah Rechtschaffen.

The three-day festival kicks off on Friday, Dec. 6, with the traditional tree lighting ceremony at 5 p.m. at Veterans Mall, featuring music by the Twice As Smart children’s choir.

The Greenfield Holiday Pop-up Market at the Pushkin Gallery starts on Friday from 4 to 8 p.m. and will continue throughout the weekend, with more than 30 participating vendors from 11 a.m. to 6 p.m. on Saturday, Dec. 7, and from 11 a.m. to 3 p.m. on Sunday, Dec. 8. Artists and artisans include Branch + Beak, Silver Owl Design, The Shiny Bunny, Fletch, Hannon Made, Thrifty Gifty, The Happy Dead, raskl, Artful Impressions, Nurselog Creations, Blossom Winks Face Painting, Sacred Smokers, Radical Rose Botanicals, Dagu Woodcraft, J.B. Smith Designs, Bonny Grant Pottery, Homestone Jewelry and more.

The GBA is collaborating with the Hawks & Reed Performing Arts Center to expand Saturday’s pop-up market to include performers, plus a gift-wrapping station. Other businesses and restaurants will be joining in on the festivities. Rechtschaffen said one of her goals is to get businesses involved that wouldn’t ordinarily be open during this time on the weekends as a way to concentrate activities and make everyone feel involved in the community, especially during such a festive time.

“A lot of them run specials.” Rechtschaffen said. “Main Street Bar and Grille has cocktail specials with holiday cocktails. Everyone comes together so that every store you pop into feels extra festive.”

Also on Saturday is the third annual Amazing Race, held in collaboration with the Greenfield Recreation Department. The Amazing Race, where teams can race around Greenfield tackling challenges and competing for prizes, will take place from 1 to 3 p.m.

“We mix it up every year, but some challenges will be the same,” said Recreation Director Christy Moore. “Some of the teams have clever names. We have the ‘Holly Jolly Ranchers’ and the ‘Blizzard Baddies.’ It’s a fun time.”

Teams are required to sign up beforehand as space is limited. Moore mentioned witnessing families pushing strollers last year, with the first-place winners of 2023 being a participating team from Stoneleigh-Burnham School.

While getting ready for the race, attendees can visit Franklin County’s YMCA for a hot chocolate bar and to spend some time with Frank, the Greenfield Police Department’s comfort dog, from 9 to 11 a.m. on Saturday. There will also be a special appearance by The Grinch.

Meanwhile, the Garden Cinemas will offer a free screening of “Santa Claus is Coming to Town,” along with free books for children, at 10:30 a.m. on Saturday.

To learn more about Jingle Fest, visit the event’s Facebook page at tinyurl.com/Jinglefest2024. To register for the Amazing Race, visit greenfieldrecreation.com/index.html.