Westport Christmas Events & Things to Do 2025
Your complete guide to the best christmas events in Westport and surrounding areas
Westport welcomes the festive season with cultural warmth along the Saugatuck Center and Main Street, offering Holiday lights and seasonal adventures around beloved landmarks like the Westport Library. Catch the Westport Holiday Stroll, A Sherlock Carol, or Gingerbread Cookie Decorating for festive events and holiday attractions that pair coastal charm with cozy activities. Explore holiday markets, seasonal performances, and waterfront strolls that make the town a bright, family-friendly destination this Christmas season.
Find the best Westport Christmas happenings this year!
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Christmas Markets
35 eventsIndoor winter village holiday market
Christmas Shows
15 eventsAmerican Christmas music concert with audience carols
Christmas Lights
12 eventsLargest indoor holiday wonderland in the Northeast
Christmas Parties
5 events1920s glamour in a historic estate
Christmas Activities
33 eventsTraditional community Christmas parade with Santa.
Editor's Picks (6)
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NRNY Holiday Market
(New Rochelle)
Indoor winter village holiday market
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Light the Lights – Winter Festival
(Danbury)
Official lighting of a 40-foot holiday tree and Santa's fire truck arrival.
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The Holiday Wish Express
(Stamford)
Largest indoor holiday wonderland in the Northeast
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Westport Holiday Stroll
Downtown holiday market with over 100 participating businesses and Santa's headquarters.
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Greenwich Reindeer Festival & Santa's Workshop
(Greenwich)
Live reindeer and Santa photos at a nursery.
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Westchester's Winter Wonderland Drive-Thru Holiday Light Extravaganza
(Valhalla)
1.2-mile drive-thru holiday light show with app integration.
Events Happening Soon (6)
Westport Christmas Events Map
See every Christmas event, light display, and market on one map.
Also Near Westport
Christmas Events Road Trips & Weekend Getaways
Worth the drive for more holiday events near Westport!
Westport Christmas FAQ
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.
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.
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.
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.
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.
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.