2026 holiday season
3 holiday markets, Christmas bazaars, and craft shows in Oak Bluffs 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 Oak Bluffs holiday fair is Featherstone Holiday Gift Show on Nov 7, 2026, and the last is Cook the Vineyard: 2026 Holiday Cookie Market on Dec 5, 2026. 2 are in November, and 1 in December. Venues this year include Featherstone Center for the Arts, Union Chapel, Inkwell Beach Club.
Oak Bluffs accounts for 3 of the 164 holiday fairs listed in Massachusetts. See the Massachusetts holiday craft fair list for shows within driving distance, or every Oak Bluffs craft fair for events outside the holiday window.
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Oak Bluffs has 3 holiday craft fairs listed between Nov 7, 2026 and Dec 5, 2026: Featherstone Holiday Gift Show (Nov 7, 2026); The Vineyard Artisans Fall Festival (Nov 27, 2026); Cook the Vineyard: 2026 Holiday Cookie Market (Dec 5, 2026).
This season's Oak Bluffs holiday fairs are at Featherstone Center for the Arts, Union Chapel, Inkwell Beach Club. 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 Massachusetts holiday page for shows in nearby towns.