Westport Christmas Events 2026
Your guide to the best Christmas events in Westport and nearby
As the holidays draw near, the shores around Westport transform, offering a familiar, comforting glow. The season here brings together a charming mix of local gatherings, from bustling markets filled with handcrafted gifts to dazzling light displays that illuminate the winter nights. You'll find community tree lightings, cheerful concerts, and theatrical performances that capture the spirit of the season.
This year, look forward to the return of the Westport Holiday Stroll, a beloved local tradition, alongside unique events like the lively NRNY Holiday Market. Closer to home, the Winter Market promises another delightful way to embrace the holiday cheer.
Browse Christmas Near Westport by Category
Christmas Markets
Holiday craft festival with artisan vendors.
Christmas Shows
Literary mashup of Dickens and Doyle with Sherlock Holmes.
Christmas Lights
Annual tree lighting ceremony with Santa's fire truck arrival.
Christmas Parties
1920s glamour in a historic estate
Unique & Unusual Christmas Events
Annual tree lighting and holiday parade
Editor's Picks
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Westport Holiday Stroll
Downtown holiday market with over 100 participating businesses and Santa's headquarters.
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A Sherlock Carol
Literary mashup of Dickens and Doyle with Sherlock Holmes.
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Westport Winter Market
Downtown holiday market with gingerbread village and Santa visits.
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Gingerbread Cookie Decorating
Two gingerbread cookies per ticket for decorating.
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The Holiday Wish Express
· Stamford
Largest indoor holiday wonderland in the Northeast
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Light the Lights – Winter Festival
· Danbury
Annual tree lighting ceremony with Santa's fire truck arrival.
Westport Christmas Events Map
See every Christmas event, light display, and market on one map.
Christmas Events in Nearby Cities
Christmas Events Road Trips & Weekend Getaways
Bigger holiday scenes worth the drive
Westport Christmas FAQ
What are the biggest annual Christmas events in Westport?
The biggest annual events include the Westport Christmas Market and the Westport Santa Dash, both held in December. These events bring the community together with festive shopping, races, and holiday entertainment.
What holiday traditions are unique to Westport?
Westport’s holiday traditions include its vibrant Christmas Market featuring local artisans and festive beverages, as well as community races like the Santa Dash that combine holiday spirit with fitness and fun.
Which neighborhoods are best for Christmas lights in Westport?
The Historic Westport District and surrounding residential neighborhoods are known for their charming and well-decorated Christmas lights, offering both walkable and drive-through viewing options.
Where can I find Christmas markets and local makers in Westport?
The Historic Westport District hosts the main Christmas Market, where you can find a curated selection of local makers, artisan vendors, and festive food and drink stalls during the holiday season.
What are the best free or budget-friendly holiday activities in Westport?
Free neighborhood light displays, strolling through the Westport Christmas Market, and attending community events like caroling and visits with Santa offer budget-friendly ways to enjoy the season in Westport.
What are good picks for families with kids in Westport?
Families can enjoy the Westport Christmas Market’s kid-friendly activities such as letters to Santa, holiday crafts, and the Elf Dash race for children, making it a festive and engaging experience for all ages.
Today's Trending Event
One of today's most-visited holiday events from across the country.
Canad Inns Winter Wonderland
📍 Winnipeg , MB , Canada
Western Canada's largest drive-through light show.
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