KENT, Conn.—Kent kicked off the holidays in style this weekend with back-to-back celebrations started on a cold but clear Friday night, Nov. 28, when a crowd gathered at town hall to light the community tree and listen to Christmas music offered up by the Kent School Concert Choir, led by director of choirs Chris Wynkoop.

Santa shares a special moment with Olivia and Harper Triplett during Friday’s lighting of the town’s Christmas tree at town hall. Photo by Kathryn Boughton
Hope Willis and her canine friend were in a holiday mood Friday as they waited for Santa to arrive to light the community Christmas tree Friday at the town hall. Photo by Kathryn Boughton

The chill was chased by cups of hot chocolate and plates of cookies provided by the Fife ‘n Drum restaurant and the tree-lighting honors were done by Santa, himself. 

Fife ‘n Drum owner Elissa Potts served up hot chocolate and cookies during the annual town tree lighting ceremony at town hall Friday. Photo by Kathryn Boughton

The Jolly Old Elf didn’t bring his support staff on his flying visit to Kent. Left without his fleet-footed team, he arrived on a fire truck thoughtfully provided by the Kent Volunteer Fire Department. Children swarmed around him as he dismounted from the vehicle and made his way toward the tree for the countdown before throwing the switch that lit the lights.

Little people swarmed around Santa after his arrival at the community Christmas tree lighting Friday at town hall. Photo by Kathryn Boughton
Members of the Kent School Concert Choir, led by director Chris Wynkoop, in white sweater, provided holiday music Friday. Photo by Kathryn Boughton

The mood shifted Saturday afternoon, Nov. 29, when the town threw its Sip, Sparkle and Stroll event, an adult party for those over 21. About 550 revelers presented tickets, gathered their glasses and made their way along Main Street where they stopped at participating businesses for bubbly libations, both alcoholic and non-alcoholic, and sipped while they shopped. 

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Kent’s Main Street glowed with holiday lights Saturday during the Chamber of Commerce’s Sip Sparkle and Stroll. Photo by Kathryn Boughton

The streets sparkled with Christmas lights, including 100 handcrafted stars wrapped in glittering lights and placed in front of the businesses. Music played over loud speakers at either end of the street, while hometown boys Rory Dolan and Sean Bemand played Christmas tunes on Falcon Field.

Matt and Daniela Rosado and Jessica and Daniel Jackson stopped by the information center sponsored by the Kent Land Trust on Main Street to warm their hands and chat with Melissa Cherniske and Connie Manes, who offered fruit-infused water and s’mores along with advice about the event. Photo by Kathryn Boughton
Barbara Boccuzzi and Jacqueline James came to Kent from Bridgewater and New Milford Saturday night to enjoy Sip, Sparkle and Stroll, the Chamber of Commerce’s Christmas event. They found much to admire at Terston. Photo by Kathryn Boughton
Leeya Beeten, accompanied by Miles and Raven, dances to the music provided by Sean Bemand and Rory Dolan on Falcon Field Saturday night. Photo by Kathryn Boughton

The season is now well and truly underway. Next weekend brings the Kent Volunteer Fire Department’s Parade of Lights. The parade is open to all and line up is at 5 p.m.; the parade kicks off at 6 p.m. To reserve a spot, call 860-488-1239.

Following the parade the public is invited to the firehouse at 28 Maple St. for food, a fire pit and visits with Santa. And that same weekend, the fire department will hold its Stuff-a-Truck event Saturday and Sunday, Dec. 6 and 7, at the firehouse, 28 Maple St.

Concerts are planned for Dec. 12, 13 and 14 when St. Andrew’s Church holds its Music in the Nave series, inviting residents to take part in the annual Messiah Sing-in at 8 p.m., Friday, Dec. 12, at the church. On Saturday and Sunday, the Kent Singers present their holiday concert, “All This Time,” an homage to the Festival of Lessons and Carols, at 3 p.m., also at St. Andrew’s.

Kent Memorial Library was abuzz with visitors during Saturday’s Sip, Sparkle and Stroll. Photo by Kathryn Boughton

Kathryn Boughton has been editor of the Kent Dispatch since its digital reincarnation in October 2023 as a nonprofit online publication. A native of Canaan, Conn., Kathryn has been a regional journalist...

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