Darien's 'Spirit Of The Season' Is Back For 2025: Here Are The Details

DARIEN, CT — The town of Darien will kick off the holiday season with a series of community celebrations throughout late November and December, featuring festive lights, caroling, Santa visits, and a menorah lighting ceremony.

Organized by the Darien Chamber of Commerce, Darien Parks and Recreation, and the Darien Sport Shop, the "Spirit of the Season" events are designed to bring residents together in the heart of town for holiday cheer and charitable giving.

Saturday, Nov. 29 — Town-Wide Holiday Lights and Shop Small Saturday

Residents are invited to experience downtown Darien under festive holiday lights while supporting local and small businesses. The Darien Chamber of Commerce will lead an effort to encourage residents to shop small.

Sunday, Nov. 30 — Annual Tree Lighting (4:30 p.m.–5:30 p.m.)

The annual tree lighting at the Darien Sport Shop will feature holiday music, hot chocolate provided by the Boy Scouts, and mini candy canes from Parks and Recreation. Santa will make a special appearance at 5 p.m. aboard a fire truck.

Saturday, Dec. 6 — An Old Fashioned Holiday (2 p.m.–5 p.m.)

Darien Parks and Recreation will host this event at Tilley Pond Park, offering caroling by the Darien High School Tudor Singers, crafts, cookie decorating, a holiday market, and ice sculptures, including a live ice-sculpting demonstration. Families can also enjoy photo opportunities.

Wednesday, Dec. 17 — Hanukkah Celebration and Menorah Lighting (6 p.m.)

A community menorah lighting will take place in Grove Street Plaza. The event includes songs, food, giveaways, and kids’ crafts. A six-foot-tall menorah will continue to be lit each night of Hanukkah at 6 p.m. by a different Jewish family from Darien.

Santa’s Letter Box

Children can drop off letters to Santa and the North Pole at the Darien Sport Shop or the Darien Parks and Recreation Office. The final day to submit letters is Dec. 10 to allow time for Santa to respond before Christmas.

Hanukkah Giving

Residents attending the Hanukkah celebration are encouraged to bring an unwrapped toy for donation. This year’s toy drive will benefit the Open Doors Shelter.