The first Randolph Fair was held on October 15, 1858, beside the road on Route 44. The vegetables, fruits, and grains were shown in the schoolhouse. The admission price in 1858 was 10 cents per person and 10 cents per horse and buggy. One story in the minutes of the society was the terrible traffic jam which occurred when horses and buggies were tied to the fence on the drive coming into the fair, and no one could get past them to come into the fair.