2026 holiday season
3 holiday markets, Christmas bazaars, and craft shows in Middletown from Nov 21, 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 1 whose name says holiday.
The first Middletown holiday fair is ALL THINGS SIS! Market on Nov 21, 2026, and the last is Kids Markets at Carol Sing At The Mansion on Dec 21, 2026. 1 is in November, and 2 in December. Venues this year include Giuseppe's Place, 44 Maynard St, The Wadsworth Mansion at Long Hill.
Middletown accounts for 3 of the 56 holiday fairs listed in Connecticut. See the Connecticut holiday craft fair list for shows within driving distance, or every Middletown craft fair for events outside the holiday window.
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Middletown has 3 holiday craft fairs listed between Nov 21, 2026 and Dec 21, 2026: ALL THINGS SIS! Market (Nov 21, 2026); Jingle All the Way- Holiday Vendor Event 12/13 (Dec 13, 2026); Kids Markets at Carol Sing At The Mansion (Dec 21, 2026).
This season's Middletown holiday fairs are at Giuseppe's Place, 44 Maynard St, The Wadsworth Mansion at Long Hill. 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.