Middlesex County Fairs & Festivals 2026
7 events across 6 towns in Middlesex County, Connecticut.
Featured
AgriculturalFamilySeasonal
Durham Fair
Connecticut’s largest agricultural fair — livestock, giant vegetables, midway, and concerts.
Sep 24–27Durham
FreeAgriculturalFamily
Middlesex & New Haven County 4-H Fair
A century-old 4-H fair at the fairgrounds — youth livestock and home-arts judging.
Fri–Sun, Jul 31 – Aug 2Durham
Food FestivalMusic
Shoreline Wine Festival
A late-summer Connecticut wine festival in Clinton — local wineries, food trucks, and music.
Sat–Sun, Aug 22–23Clinton
AgriculturalFamilySeasonal
Chester Fair
A River Valley late-summer fair — 4-H shows, a famous pie contest, and tractor pulls.
Fri–Sun, Aug 28–30Chester
AgriculturalFamilySeasonal
Haddam Neck Fair
A Labor Day River Valley fair — livestock, oxen draws, a midway, and live entertainment.
Sep 4–7Haddam Neck
AgriculturalFamilySeasonal
Portland Agricultural Fair
A River Valley October fair — livestock, tractor pulls, and farm competitions.
Fri–Sun, Oct 2–4Portland