Holiday Happenings in Westport, CT (2024)

Holiday Happenings in Westport, CT (2024)

  • 11/19/24

The weather has been unseasonably warm, but with Thanksgiving just around the corner and the holidays are quickly approaching.  Here in beautiful Westport, CT, the magic of the holidays is already in the air. Westport has a wonderful lineup of events to make your holiday season unforgettable, from festive family activities to cultural celebrations and enchanting performances.

Sweeten Your Holidays with Wakeman Town Farm's Thanksgiving Pie Sale In Support of Earth Animal's 17th annual Mitten Project to benefit CTFoodShares

Don't forget to order your delicious Thanksgiving pies from Wakeman Town Farm! Support CT FoodShare while enjoying a delectable treat. Place your order by Friday, November 22nd, and pick up your pies on Monday, November 25th. (Link: Thanksgiving Pie Sale)

Don't Miss the Westport Holiday Stroll!

Kick off the holiday season with the Westport Holiday Stroll on Saturday, December 7th. Stroll through the charming downtown streets, admire the beautifully decorated storefronts, and indulge in holiday shopping. Keep an eye out for Gilbert the Party Pig, dressed as a reindeer and spreading holiday cheer! The Riverside Realty Group is proud to sponsor Gilbert and this festive event.

In addition to the Holiday Stroll, here are a bunch of other great holiday events around town:

Light Up Your Holidays:

  • Westport Annual Tree Lighting Ceremony (December 1st): Kick off the holiday season with the official lighting of Westport's beautiful Christmas tree! This festive event features carolers, hot chocolate, and a special appearance by Santa Claus. It's the perfect way to usher in the holiday spirit and create lasting memories. (Details: Westport Annual Tree Lighting Ceremony)
  • Winter Market (December 7th): Immerse yourself in the holiday spirit at the Westport Museum's Winter Market. Explore a charming gingerbread village showcasing local landmarks, browse unique gifts from local vendors, warm up by the fire with a cup of hot chocolate, and capture the magic with a photo with Santa! This free, family-friendly event is the perfect way to kick off your holiday cheer.

Musical Delights:

  • Staples High School's 84th Annual Candlelight Concerts (December 13th & 14th): Immerse yourself in the warm glow of candlelight as you experience the Staples High School's 84th Annual Candlelight Concerts. This beloved tradition features the school's talented choral groups performing a selection of seasonal classics. Be sure to get your tickets early, as these concerts tend to sell out quickly! Tickets go on sale at 9 am Monday, Novemeber 25th. (Details: Staples High School's 84th Annual Candlelight Concerts)

Celebrating Traditions:

  • Cultural Fellowship (December 12th): Embrace the diverse tapestry of winter celebrations at the Westport Museum's Cultural Fellowship. Enjoy a cozy atmosphere with a warming fire, festive music, and delicious treats. Learn about a variety of cultural traditions celebrated in Westport and beyond, including Indigenous winter festivities, Hannukah, Kwanzaa, Lunar New Year, Christmas, and many others. This free event is a wonderful opportunity to experience the richness of different cultures and traditions.

Festive Fun for All Ages:

  • Gingerbread Cookie Decorating (December 14th): Unleash your creativity and indulge your sweet tooth at the Westport Museum's Gingerbread Cookie Decorating event. Decorate your very own gingerbread cookies with a friend or family member, choosing from a delightful selection of candy and icing. This fun and festive activity is a perfect way to bond with loved ones and create delicious seasonal souvenirs.
  • Holiday Wreath Workshop (December 1st): Craft the perfect holiday decoration at the Westport Museum's Holiday Wreath Workshop. Learn the art of wreath making from experienced instructors and create a beautiful and festive wreath to adorn your home for the season. (Link: Holiday Wreath Workshop)

A Theatrical Treat:

  • A Sherlock Carol (December 17th - 22nd): The Westport Country Playhouse presents a unique holiday twist - "A Sherlock Carol." This captivating performance combines the classic tales of Sir Arthur Conan Doyle's "The Adventure of the Blue Carbuncle" and Charles Dickens' "A Christmas Carol," creating a brand new mystery perfect for all ages. Immerse yourself in the world of Sherlock Holmes during the festive season and enjoy a heartwarming and suspenseful performance.

Beyond This List:

Don't forget to explore the additional activities offered throughout December in Westport! Here are a few more to consider:

  • Westport PAL Ice Rink at Longshore
  • Cozy up at Westport’s inviting cafés like Terrain or Studio Cafe at The Tailored Home
  • Visit Sherwood Island State Park, where you can take in the tranquility of nature during the colder months. For a peaceful stroll along the river, head to the Library Riverwalk and Garden, or explore the newly updated Riverside Park, offering fresh perspectives and inviting spaces for a winter walk.

Make Your Holidays Sparkle in Westport!

Westport offers a charming and festive atmosphere to celebrate the holidays. With a variety of events to choose from, you're sure to find the perfect way to create lasting memories with your loved ones. So bundle up, embrace the holiday cheer, and enjoy the magic of the season.

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