Holiday Festivities in Fairfield County | Celebrate the Season in Style
Market Intel
Market Intel
WESTPORT | A WINTER WONDERLAND
Westport Annual Tree Lighting Ceremony
Date: December 1, 2024
Gather with friends and family to watch the lighting of Westport’s iconic tree. With carolers, hot chocolate, and Santa on hand, it’s a magical evening for all.
Winter Market at the Westport Museum
Date: December 7, 2024
This family-friendly event brings the holiday spirit to downtown Westport. Enjoy a gingerbread village of local buildings, explore local vendor booths, enjoy the warming fire and hot chocolate, and much more.
Staples High School Candlelight Concerts
Dates: December 13 & 14, 2024
Experience the ethereal beauty of holiday music performed by talented students in a candlelit setting. A cherished tradition for over 80 years.
A Sherlock Carol at Westport Country Playhouse
Dates: December 17–22, 2024
A unique blend of detective intrigue and holiday charm, this theatrical performance offers a new twist on A Christmas Carol.
FAIRFIELD | FESTIVE FAMILY FUN
Brunch & Dance Party with Santa
Date: December 8, 2024
Celebrate the season with food, fun, and dancing, capped off with a visit from Santa Claus.
WILTON | HOLIDAY HERITAGE
Great Trains Holiday Show
Date: December 7, 2024
The Wilton Historical Society transforms into a wonderland of model trains. A delightful event for train enthusiasts and families alike.
Breakfast with Santa at Cannon Grange
Date: December 14, 2024
Treat the kids to breakfast and a visit with Santa in this charming, historic setting.
EASTON | SEASONAL CHEER
Holiday Tree Lighting
Date: December 8, 2024
Celebrate the season with a sing-along, crafts, hot chocolate and more.
REDDING | HANDS-ON HOLIDAY FUN
Holiday Felt Ornaments: A Beginner’s Craft Class
Date: December 13, 2024
Kick off your holiday season by learning to create beautiful felt ornaments at New Pond Farm - perfect for gifting or decorating your home!
DARIEN | HOLIDAY SHOPPING
Holiday Market at Darien Community Association
Dates: December 5–7, 2024
Discover unique gifts from local artisans and vendors at this festive market.
NEW CANNAN | A PICTURE-PERFECT STROLL
Holiday Stroll
Date: December 6, 2024
Take in the festive ambiance of downtown New Canaan, with beautiful decorations, live music, and plenty of holiday cheer.
WESTON | THE SPIRIT OF THE SEASON
Holiday Festival and Tree Lighting
Date: December 5, 2024
Celebrate the season with music, hot chocolate and holiday cheer.
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CELEBRATE THE SEASON YOUR WAY
From festive gatherings to heartwarming performances and hands-on workshops, Fairfield County has something for everyone.
Gather your loved ones, bundle up, and make memories to last a lifetime this holiday season.
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