A Fair Tradition Since the 1800s
Early Beginnings
The Sterling Fair traces its roots back to the early 1800s when it was organized by the Sterling Cattlemen’s Association. Local farmers pooled their resources to create an agricultural fair held on Sterling Common, utilizing the town hall and three local churches. For generations, the fair celebrated farming, community, and rural life before eventually ending in the late 1950s due to a shortage of volunteers.
A Bicentennial Revival
In 1981, as part of Sterling’s Bicentennial celebration, the fair was revived as a municipal event operated by the Town of Sterling. The first modern fair was held behind the fire station at the Memorial area. Just one year later, it moved to Houghton School, where the fair continued to grow in both size and popularity.
Finding a New Home
By the late 1990s, the fair had outgrown its location. In 1999, with construction underway for the new Chocksett School, Sterling Air owner Jimmy Simpson and airport landowner Henry Ciborowski generously offered the use of Sterling Airport. Their support ensured the fair could continue and provided the space needed for future growth.
Powered by Volunteers
Today, the Sterling Fair is one of the largest free fairs of its kind in New England, welcoming between 30,000 and 40,000 visitors each year. Despite its size, the fair operates on a lean budget and has no permanent home. Everything is made possible by volunteers—from the 20-member Fair Committee who work year-round to the more than 50 volunteers who dedicate countless hours before, during, and after the fair.