Woodstock Fair
August 28 - September 1, 2025
Celebrating its 163rd year, this is the state's second-oldest agricultural fair!
Haddam Neck Fair
August 29 - September 1, 2025
The Haddam Neck Fair is celebrating its 105th year and is in one of the most beautiful parts of the state, not far from the Goodspeed Opera House and the CT River.
Goshen Fair
August 30 - September 1, 2025
Goshen gets down with some truly fun Fair activities: An adult spelling bee, a hay bale toss contest, and a pie-eating contest.
North Haven Fair
September 4-7, 2025
Known for bringing in some great live music acts, bring the kids to Old MacDonald’s Farm for a kids pie eating contest.
Bethlehem Fair
September 5-7, 2025
Bethlehem revels in all things old-fashioned.
Guilford Fair
September 19-21, 2025
My personal favorite! Once known for booking up-and-coming country music artists, they still stick one in during their three-day run every September. This year it's Houston Bernard on the last day of the Fair. Prior to that it's tribute bands, from Fleetwood Mac to - believe it or not - Guns 'n Roses. Plus, the food!
Durham Fair
September 25-28, 2025
Begun in 1916, the Durham Fair continues its tradition today as Connecticut’s largest agricultural fair. And talk about big names when it comes to live music. This year come sail away with none other than Styx!
Harwinton Fair
October 3-5, 2025
The Harwinton Fair offers good old-fashioned fun for all! See the Pig Races, Antique Tractor Show, Rabbit Costume Contest, Oxen Draw, and Civil War Displays. Enjoy a magic show and bluegrass music after visiting the barnyard animals. Stop by the Country Store for a memento of your special day!
Portland Fair
October 3-5, 2025
The Portland Fair gives Fair enthusiasts one of their last chances of the season to experience all the classic fair entertainment, food, exhibits, animals, and activities for the year.
Riverton Fair
October 10-12, 2025
Old-fashioned country fair on scenic Farmington River.