Leave a Message

Thank you for your message. We will be in touch with you shortly.

Holiday Festivities in Fairfield County | Celebrate the Season in Style

Market Intel

The holiday season is upon us, and Fairfield County is bursting with festive cheer!
From charming tree lightings to magical concerts and holiday markets, there’s plenty of holiday fun to be found in our local communities with activities and events to get everyone into the holiday spirit.
Check out the list below to get your holiday season started!
***

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.

 ***

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.

 


Work With Deirdre

With an extensive network of industry contacts and in-depth knowledge of the local market activity, both on and off the MLS, She is a seasoned Real Estate Agent. She represents home buyers and sellers, from the first-time homebuyer to the experienced seller, often advising the same clients through multiple transactions.

Follow Me On Instagram