Barns, Bands & Big Fun: Your Guide to Connecticut’s Fair Season!
It’s Fair Season in Connecticut!
The past couple of weeks in Connecticut have shouted fall–crisp mornings, pumpkin-flavored everything sneaking its way onto the menu, and daylight disappearing sooner than my iced coffee order. While I’m not quite ready for the days to get shorter, I am starting to get excited about one of my favorite fall festivities: fair season!
All across the state, communities are gathering for weekends filled with rides, games, live music, and delicious fair food - fried dough anyone?! From classic agricultural showcases to contests and cultural celebrations, there’s something for everyone to enjoy.
Things start to begin in late August, when towns like Cheshire, Brooklyn, Terryville, and Chester host their local grange and country fairs. These smaller gatherings are full of small-town excitement (think pie contests, craft tents, tractor pulls, and neighbors catching up over ice cream cones). At the same time, big-name fairs like Woodstock, Haddam Neck, and Goshen draw huge crowds with midway rides, fireworks, livestock shows, and tons of live entertainment!
September is when fair season REALLY picks up though! The Wapping Fair in South Windsor is a family favorite, blending livestock exhibits with magic shows, rides, and rows of food vendors. A week later, the Four Town Fair in Somers -my personal favorite having grown up in Somers- brings the fun with its famous parade, contests, antique car show, rides, and mouth-watering fair food that keep people coming back year after year. Community gems like the Berlin Lions Agricultural Fair and the Norfield Grange Fair also add their own flavor to the calendar, reminding us just how many ways Connecticut knows how to celebrate.
By mid-September, the spotlight shifts to the Guilford Fair and then the Durham Fair—the state’s largest—where you’ll find everything from animal barns to nationally known musical acts. But don’t pack away your comfortable fair shoes too soon because October brings plenty more! The Harwinton Fair and Riverton Fair each have their own mix of history and family fun, while the Portland Agricultural Fair keeps traditions alive with rides, contests, and local food. You can also branch out beyond the classic fairs: celebrate heritage at the Highland Games of Scotland in Brooklyn or get into the fall spirit at the Milford Pumpkin Festival.
No matter where you are in Connecticut this season, chances are there’s a fair just around the corner. So grab your friends, pack some extra napkins (or baby wipes–I don’t travel without them!) for the fried dough, and get ready to make the most of this fair season!
And don’t forget—each week we’ll be sharing highlights and schedules from these fairs on our social media, so follow along to plan your perfect fair weekend!
