Top Holiday Events in Westport

The holiday season in Westport, Conn., is a magical time filled with festive events that bring the community together. From creative workshops to charming markets, Westport transforms into a hub of holiday cheer, offering activities for all ages. Families can enjoy hands-on experiences, like decorating gingerbread cookies, while couples and friends can stroll through winter markets or join in on caroling traditions. Whether you’re a longtime resident or visiting for the first time, Westport’s holiday events provide the perfect way to celebrate the season, making unforgettable memories with loved ones in this beautiful New England town.

Join the festive fun at Breakfast with Santa on December 14 and 15 from 9:30 to 10:30 a.m. Enjoy a delicious buffet-style breakfast featuring scrambled eggs, pancakes, bacon, sausage, bagels, fruit, and donuts, all served with coffee and hot cocoa. Kids can color festive pages to take home, adding to the holiday joy. This family-friendly event is hosted by Stew Leonard’s, which is known for providing fresh and quality food experiences.

On December 6, enjoy Linda Eder’s incredible vocal range across Broadway, Pop, and Jazz. Known for her role in Jekyll & Hyde, she brings holiday favorites and original songs to life, promising a memorable evening. Her performances are praised for their emotional depth and versatility, captivating audiences with every note. Don’t miss this opportunity to see one of America’s most celebrated voices in an intimate setting.

December 8 brings a joyful afternoon of seasonal music, with proceeds benefiting Ability Beyond. This concert celebrates the spirit of the season and supports vital programs for people with disabilities. The casual and fun atmosphere makes it perfect for all ages, featuring contemporary holiday songs that will have everyone singing along. It’s an event that combines great music with the joy of giving back to the community.

Join the Ridgefield Conservatory of Dance on December 13 for their enchanting Nutcracker performance. Celebrate 60 years of dance excellence with a magical evening of Tchaikovsky’s classic, complete with a pre-show reception featuring treats for all ages. The production features a talented cast of students, professionals, and guest performers, creating an unforgettable holiday tradition. The dazzling costumes and set design bring this timeless story to life, making it a must-see for families.

Experience a festive blend of Irish Christmas carols, lively dance, and contemporary songs on December 18. Known for their PBS-TV special, the Celts offer a unique mix of modern holiday hits and traditional Irish music featuring standout artists like Emerald Rae and Patrick D’Arcy. Each performance showcases new songs and dance numbers, ensuring a fresh and exciting experience year after year. It’s a family-friendly event filled with joy and vibrant Celtic traditions.

Presented by the Westport Downtown association and Dan Woog’s 0660 Blog this year's event will be held Sat Dec 7th and will  feature participating retailers and restaurants offering deals and promotions, activities for children (face painting, s’mores, Santa photos, and more), and performances by the Staples High School Orphenians on Upper Main Street, Lower Main Street, corner of Post and Main outside Anthropologie, and Sconset Square. The Elm & Main complex or 136 Main Street will serve as the headquarters of Holiday Stroll with Santa, DJ, photo booth, and much more.

The Holiday Winter Market on Elm Street (Sigrid Schultz parking lot) will feature a variety of vendors for your shopping pleasure. (See participating vendors below). The Westport Police Department will host a toy drive, so please bring a new toy. A vintage firetruck courtesy of the Westport Fire Department will be on-site to delight children.

Get into the holiday spirit with Gingerbread Cookie Decorating at the Westport Museum for History & Culture. One ticket provides you with two gingerbread cookies and plenty of candy and icing to make your creations come to life. Enjoy decorating with friends, family, or your favorite person in this festive setting. Museum staff will be on hand to offer tips and decorating suggestions, making it a delightful and creative experience for all ages. Take home your decorated cookies as a sweet holiday keepsake!

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