Middlesex County Fairs & Festivals 2026
Listed here: 7 events, all ended for 2026.
EndedAgriculturalFamilySeasonal
Durham Fair
A late-September agricultural fair. Livestock, giant vegetables, midway, and concerts.
Sep 24–27Durham
EndedAgriculturalFamilySeasonal
Portland Agricultural Fair
A River Valley October fair. Livestock, tractor pulls, and farm competitions.
Fri–Sun, Oct 2–4Portland
EndedAgriculturalFamilySeasonal
Haddam Neck Fair
A Labor Day River Valley fair. Livestock, oxen draws, a midway, and live entertainment.
Sep 4–7Haddam Neck
EndedAgriculturalFamilySeasonal
Chester Fair
A River Valley late-summer fair. 4-H shows, a pie contest, and tractor pulls.
Fri–Sun, Aug 28–30Chester
EndedFood FestivalMusic
Shoreline Wine Festival
A Connecticut wine festival in Clinton. Local wineries, food trucks, and music.
2026 date not confirmedClinton
EndedFreeAgriculturalFamily
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
EndedFreeCulturalMusicFamily
Deep River Ancient Muster
A fife-and-drum muster at Devitt Field. Colonial corps, a tattoo, and a parade.
2026 date not confirmedDeep River