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2026 holiday season
3 holiday markets, Christmas bazaars, and craft shows in Westport from Nov 7, 2026 through Christmas Eve.
Every craft fair and market from November 1 through Christmas Eve is listed, since that is when holiday shopping happens. 🎄 Holiday marks the 2 whose name says holiday.
The first Westport holiday fair is CraftWestport on Nov 7, 2026, and the last is Cookie Walk & Holiday Gift Market on Dec 12, 2026. 1 is in November, and 2 in December. Venues this year include Staples High School, 75 Church Ln, United Methodist Church of Westport & Weston.
Westport accounts for 3 of the 122 holiday fairs listed in Connecticut. See the Connecticut holiday craft fair list for shows within driving distance, or every Westport craft fair for events outside the holiday window.
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Westport has 3 holiday craft fairs listed between Nov 7, 2026 and Dec 12, 2026: CraftWestport (Nov 7, 2026); THE MARKET - A Charitable Holiday Gift Market in Westport (Dec 5, 2026); Cookie Walk & Holiday Gift Market (Dec 12, 2026).
This season's Westport holiday fairs are at Staples High School, 75 Church Ln, United Methodist Church of Westport & Weston. Each listing has the address and hours.
Most holiday shows close vendor applications one to three months out, so apply early. Open a listing for its application link, and see the Connecticut holiday page for shows in nearby towns.