Fun Is Just Around the Corner at the Windsor Fair. Are you searching for an event to relieve your summer boredom? A trip to the Windsor Fair will do the trick. The Windsor Fair is opening again next summer, and you won't want to miss out on all the fun we have planned. Our fair is more than 50 acres of amusement. Your friends and family will enjoy a fun day together while visiting our many attractions. You can even participate in some of our events. From daily shows to a large animal exhibit, everyone can find something to love at the Windsor Fair. Our 2019 season runs from Aug. 25 to Sept. 2. Visit us as soon as we open to enjoy all that the Windsor Fair has to offer.