09/04/2026
☺️ Labor Day weekend is here, and we're soaking up every last bit of summer! From classic agricultural fairs and Greek food to corn mazes and cider donuts, here’s what’s happening around Connecticut:
🎡 Woodstock Fair (September 3–7) – Woodstock, CT
The Woodstock Fair celebrates its 165th year this Labor Day weekend! As Connecticut’s largest and second-oldest agricultural fair, it’s packed with livestock shows, a petting zoo, free stage shows, a midway, agricultural exhibits, strolling entertainers, and plenty of delicious fair food.
🇬🇷 Odyssey Greek Festival (September 4–7) – Orange, CT
Take a trip to Greece without leaving Connecticut at the 44th annual Odyssey Greek Festival! Enjoy live Greek music and dancing, cooking demonstrations, church sanctuary tours, kids’ activities, and plenty of authentic Greek dishes including gyros, souvlaki, spanakopita, moussaka, and baklava. New this year, relax in the festival’s Taverna with Greek wine or beer and live music!
🌽 Corn Maze & Cider Donut Festival (September 5–6) – Middlefield, CT
Kick off the unofficial start of fall at Lyman Orchards tomorrow and Sunday! Celebrate the opening of the 2026 corn maze, themed around 250 Years of the USA, while enjoying pick-your-own fruit, goat cuddling, wagon rides, square dancing, live music, and family activities. And of course, don’t miss the cider donuts—including a special cider donut sundae and even a cider donut hole co****le toss!
🐴 Goshen Fair (September 5–7) – Goshen, CT
Spend Labor Day weekend at the Goshen Fair, a celebration of Connecticut’s agricultural roots! Check out livestock judging, draft horse and oxen pulls, woodcutting and truck pulls, live entertainment, a midway, rides, exhibits, and classic fair food. You can also join in on quirky competitions like the frozen T-shirt contest, hay bale toss, apple fritter eating contest, and skillet throw!
How are you spending this long weekend? Let us know in the comments!
📍Videos taken in New Haven, CT