Middlesex County Fairs & Festivals
13 events in Middlesex County, Connecticut for 2026.
★ FeaturedDurham Fair
Connecticut’s largest agricultural fair — livestock, giant vegetables, midway, and concerts.
Deep River Ancient Muster
The world’s largest fife-and-drum muster — colonial corps, a tattoo, and a parade.
4.8(18)Clinton Summer Fair
Clinton Summer Fair will be held on August 7-8, 2026.
Shoreline Wine Festival
A late-summer Connecticut wine festival in Clinton — local wineries, food trucks, and music.
Chester Fair
A River Valley late-summer fair — 4-H shows, a famous pie contest, and tractor pulls.
4.6(290)Haddam Neck Fair
A Labor Day River Valley fair — livestock, oxen draws, a midway, and live entertainment.
4.8(101)Killingworth Artisan Market
Killingworth Artisan Market will be held on September 12, 2026.
5(5)Middlefield Transcend Fest
Middlefield Transcend Fest will be held on September 18-20, 2026.
4.5(794)Durham Agricultural Fair
Durham Agricultural Fair will be held on September 24-27, 2026.
Portland Agricultural Fair
A River Valley October fair — livestock, tractor pulls, and farm competitions.
4.8(830)Old Saybrook Arts and Crafts Festival
Old Saybrook Arts and Crafts Festival will be held on October 3-4, 2026.
Clinton Holiday Craft Fair
Clinton Holiday Craft Fair will be held on December 5, 2026.
4.3(1908)Vermont Spring Home Show
Vermont Spring Home Show will be held on April 10-11, 2027.