Connecticut Fairs & FestivalsConnecticutFairs & Festivals

Middlesex County Fairs & Festivals 2026

6 events across 6 towns in Middlesex County, Connecticut.

Durham Fair — Durham, Connecticut
Featured
AgriculturalFamilySeasonal

Durham Fair

Connecticut’s largest agricultural fair — livestock, giant vegetables, midway, and concerts.

Sep 24–27Durham
Deep River Ancient Muster — Deep River, ConnecticutFree
CulturalMusicFamily

Deep River Ancient Muster

The world’s largest fife-and-drum muster — colonial corps, a tattoo, and a parade.

Sat, Jul 18Deep River
Shoreline Wine Festival — Clinton, Connecticut
Food FestivalMusic

Shoreline Wine Festival

A late-summer Connecticut wine festival in Clinton — local wineries, food trucks, and music.

Sat–Sun, Aug 22–23Clinton
Chester Fair — Chester, Connecticut
AgriculturalFamilySeasonal

Chester Fair

A River Valley late-summer fair — 4-H shows, a famous pie contest, and tractor pulls.

Fri–Sun, Aug 28–30Chester
Haddam Neck Fair — Haddam Neck, Connecticut
AgriculturalFamilySeasonal

Haddam Neck Fair

A Labor Day River Valley fair — livestock, oxen draws, a midway, and live entertainment.

Sep 4–7Haddam Neck
Portland Agricultural Fair — Portland, Connecticut
AgriculturalFamilySeasonal

Portland Agricultural Fair

A River Valley October fair — livestock, tractor pulls, and farm competitions.

Fri–Sun, Oct 2–4Portland