Westfield Fair Association, Inc. is a 501(c)(3) non-profit organization operating under the supervision of the Massachusetts Division of Fairs. We were founded originally under the name of the "Young People's Agricultural Association" in 1927. Later it was renamed the "4-H and Agricultural Society" and again changed in 1953 to be incorporated as "The Westfield Fair".

Originally held at the old Normal School grounds, it featured flowers, vegetables and sewing produced by grade school and young teen students. Next it was moved to the Westfield Women’s Club House, later the Armory on Rt. 20, and the Westfield High School. When livestock was added it became necessary to move the fair to a field at the Blanchard Farm. When the flood of ’55 struck on the weekend of the fair, and the Ferris wheel floated down stream to West Springfield, it was necessary to move again. The following year the Allen family of Wyben loaned the present property to the Fair Association, later deeding it to them. There were no buildings and cattle were tied to a rail fence. Food was served under a tent. The following year bleachers were added for those watching the oxen and horse pulls.

From its’ beginning to the present, the desire to be part of this fair association has been handed down from father to son, mother to daughter. Looking back through the original fair books, we can find the names of the grandparents and great-grandparents of many of the present members and officers of the fair today. There are many dedicated members working year round to be sure the fair runs smoothly.