Early Warning Forecast: Litchfield Holiday Events ‘Blizzard’

Litchfield’s marquee holiday celebration, the annual Holiday Stroll & Tree Lighting, will take place on Sunday, Dec. 3 (details to follow) – and it’s just one of many festive holiday events taking place this year.

Here’s an “early warning” list that we’ll add to as more things and details are announced. Also stay tuned for a separate post on special holiday shopping promotions and events like Shop Small Weekend from Black Friday (Nov. 24) through Cyber Monday (Nov. 27)

Oliver Wolcott Library Festival of Trees, Sat., Nov. 25, 5-8:30

Holiday events, Litchfield, 2023

Tickets are now available for the 2023 Festival of Trees, Oliver Wolcott Library’s magical evening of celebration. Purchase tickets online ($85 until 11/17) . The gala fund-raiser includes lavish hors d’oeuvres, wreaths and trees, and much more. “Kick off your holiday season with the party everyone in Litchfield talks about,” OWL says

Litchfield Park & Rec Holiday Bazaar, Nov. 25, 9-2

Holiday events in Litchfield 2023

Jingle Bell Run, Dec. 2, 10 a.m.

Holiday events 2023 in Litchfield

Holiday Stroll  & Tree Lighting, Sunday, Dec. 3

hoilday events in Litchfield 2023

The town’s annual Holiday Stroll & Tree Lighting takes place in the afternoon and features caroling, shopping, events at Litchfield Historial Society, horse-drawn hay rides, the arrival of Santa and Mrs. Claus, and more leading up the the lighting of the holiday tree on the Green just after dark. Stay tuned for details on this year’s event.

Glad Tidings We Sing: Waterbury Chorale Concert at St. Michael’s, Dec. 8, 7:30

holiday events 2023 in Litchfield CT

The Waterbury Chorale performs a concert at St. Michael’s Episcopal Church with 70 plus singers, a brass ensemble, organ, piano, violin, percussion and steel drums. Tickets are $25.

Breakfast With Santa, Brandywine Living at Litchfield, Dec. 9

holiday events 2023 in Litchfield CT

Save the Date to have a lovely Pancake Breakfast with Santa. Bring a gift for Santa to give your child/children. All proceeds will go to the Susan B. Anthony Project, just in time for the holidays. The cost is $10 for adults; children ages 12 and under are free. More information to follow.

Holiday Trees at Bantam Fire Company

holiday events 2023 in Litchfield CT

Breakfast With Santa and Holiday Trees at Bantam Fire Company

holiday events 2023 in Litchfield CT


Milton Resolution Road Race, Jan. 1

holiday events 2023 in Litchfield CT