Connecticut Fairs & FestivalsConnecticutFairs & Festivals

Windham County Fairs & Festivals 2026

4 events across 3 towns in Windham County, Connecticut.

Brooklyn Fair — Brooklyn, Connecticut
Featured
AgriculturalFamilySeasonal

Brooklyn Fair

One of America’s oldest continuously running fairs — ox draws, livestock, and a country midway.

Aug 27–30Brooklyn
Windham County 4-H Fair — Brooklyn, ConnecticutFree
AgriculturalFamily

Windham County 4-H Fair

A youth 4-H fair at the Brooklyn Fairgrounds — livestock, poultry, and project demonstrations.

Fri–Sun, Jul 24–26Brooklyn
Ekonk Community Grange Fair — Sterling, ConnecticutFree
AgriculturalCraftFamily

Ekonk Community Grange Fair

A one-day Quiet Corner Grange fair — baking and produce contests with a country breakfast.

Sat, Aug 8Sterling
Woodstock Fair — Woodstock, Connecticut
AgriculturalFamilySeasonal

Woodstock Fair

A big Labor Day Quiet Corner fair — livestock, demo derby, midway, and live entertainment.

Sep 3–7Woodstock