5 Winter Holiday Activities in and Around Westport, CT

5 Winter Holiday Activities in and Around Westport, CT


Westport, Connecticut, offers a delightful array of winter holiday activities that attract both residents and visitors alike. This charming coastal town, renowned for its scenic beauty and vibrant community, provides a picturesque backdrop for a variety of seasonal festivities. For those interested in homes for sale in Westport, CT, these activities not only enhance the holiday experience but also showcase the strong community spirit and family-friendly environment of the area. This guide highlights the best winter holiday activities in and around Westport, CT, perfect for making the season bright.

Festive Light Displays

One of the most enchanting aspects of the holiday season is the presence of brilliant displays of lights that illuminate the winter nights. Westport and its surrounding areas host several spectacular light shows that are sure to dazzle:

  • Festival of Lights at Sherwood Island: Just a short drive from the heart of Westport, Sherwood Island State Park transforms into a winter wonderland with its annual Festival of Lights. Visitors can drive through a magical setup of twinkling lights and festive decorations, making it a perfect outing for the whole family.

  • Norwalk’s Lantern Point Light Display: Nearby Norwalk offers an impressive light display at Lantern Point, where hundreds of handcrafted lanterns light up the area with holiday themes and imaginative designs.

Holiday Markets and Shopping

Holiday markets are a delightful way to find unique gifts and enjoy the festive atmosphere. Westport and its neighboring towns offer several markets featuring local artisans and vendors:

  • Westport Holiday Market: Located in the center of town, the Westport Holiday Market features local craftspeople and artists. It’s an excellent spot for finding one-of-a-kind gifts, from handmade jewelry to artisanal foods.

  • Fairfield Christmas Bazaar: A short drive away, Fairfield hosts an annual Christmas Bazaar that includes a wide range of vendors selling everything from holiday decorations to winter apparel. It's a great place to soak up the festive spirit while supporting local businesses.

Seasonal Performances

The arts play a significant role in Westport’s community life, with seasonal performances bringing cheer to all ages:

  • The Nutcracker at Westport Playhouse: This classic ballet is performed annually at the Westport Playhouse, featuring talented local dancers and breathtaking set designs. It’s a must-see for ballet lovers and those new to the art form.

  • Holiday Concerts at the Quick Center: Just a few miles away at Fairfield University’s Quick Center for the Arts, visitors can enjoy a variety of holiday concerts ranging from classical music to contemporary holiday hits.

Outdoor Winter Activities

For those who love the outdoors, Westport’s winter landscape provides plenty of opportunities to engage in seasonal sports and activities:

  • Ice Skating at Longshore Club Park: The ice rink at Longshore Club Park is a popular destination for families and skating enthusiasts. Offering skate rentals and hot cocoa, it’s a perfect spot to enjoy a day or evening on the ice.

  • Winter Walks at Earthplace: The trails at Earthplace offer a tranquil escape into nature, where visitors can enjoy guided winter walks and wildlife watching. It's an educational and refreshing activity suitable for all ages.

Community Holiday Events

Westport is a community that thrives on shared experiences, especially during the holidays:

  • Tree Lighting Ceremony: The annual tree lighting ceremony in downtown Westport is a highlight of the season. It features live music, hot beverages, and a visit from Santa. It's a wonderful event that brings the community together in celebration.

  • New Year’s Eve Fireworks at Compo Beach: To ring in the new year, locals and visitors gather at Compo Beach for a spectacular fireworks display over the water. This event is a festive way to say goodbye to the year and welcome the new one with friends and family.

Looking to Move to Westport or the Surrounding Areas?

The array of winter holiday activities in and around Westport, CT, not only makes the season special but also reflects the vibrant and close-knit community of the area. These festivities offer fun, joy, and a chance to make lasting memories, enhancing the appeal of living in this beautiful region. For those considering relocating to this part of Connecticut, the winter season highlights the best of what Westport has to offer.

For more information on homes for sale in Westport, CT, or to learn more about local community events and activities, reaching out to a knowledgeable real estate professional like Gina Hackett is highly recommended. Gina’s expertise will help guide you through the local real estate market and ensure you find a home that fits your lifestyle, with the added joy of community events that make every season in Westport unforgettable.



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Beyond buying and selling properties, Gina applies her deep knowledge of “all things Fairfield County” to work as an added resource for clients who are new to the area.

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