The Topsfield Fair began in February 1818 with the founding of the Essex Agricultural Society headed by Timothy Pickering. In 1820, the society held its first event, a cattle show. The intent was to have an arena in which local farmers could engage in friendly competition as well as exchange ideas and methods about agriculture. Early events at these shows included cattle shows, oxen pulls, and plowing matches. From the years of 1820 to 1895 the fair was held in a variety of locations across Essex County. In 1895, the Fair began a 15-year residence in Peabody when it bought a 50-acre plot. In 1910, the Fair moved to its current location in Topsfield, a 150-acre experimental farm that had been given to the society in 1856. Most of the agricultural and exhibition barns that are a part of the present day Topsfield Fair were erected in between 1921 and 1925. In its 200-year history, the fair has only missed the years of 1943–1945 where it was halted due to World War II.

Although not part of the original fair, the midway has become one of the major attractions of the Topsfield Fair. The midway has been a major part of the fair since 1950 when Fiesta Shows was contracted to bring rides and entertainment to the fair. Major attractions include carnival rides aimed towards all ages, carnival games, and food. The rides that are used at the fair typically are broken up into four sections by Fiesta Shows – Kid Rides, Family Rides, Major Rides, and Spectacular Rides and aim to cater to people of all ages. Rides typically cost between 3–5 tickets depending on the size and thrill of the ride which can be purchased from Fiesta Shows. In addition the Fair sells pre-sale tickets at discounted rates. Carnival games at the fair are typically "pay until you win" games such as darts, ring toss, and duck pond, or competition type games such as the water gun game.

Food at the fair is provided both by Fiesta Shows as well as local retailers and community members. Fiesta Shows runs a variety of traditional fair food stands including a hot dog and hamburger, fried dough stands, french fry stands, sausage stands, and a fried candy stand. In addition to the food provided by Fiesta shows local restaurants and communities provide a variety of more tradition New England fall food. One booth in particular run by the First Congregation Church of Topsfield has been serving turkey dinners since before 1920. In 2015 the church served over 2,500 dinners raising funds for charity. Other local food includes Whoopie pies by the Topsfield Bakeshop, a baked potato booth, and boy scout run food stands. Overall there are nearly 300 vendors selling food and other items at the fair.

According to Wikipedia

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