Westport Fair 2026
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The Westport Fair is a five-day summer agricultural fair on Pine Hill Road in Westport, MA, established in 1955 by Voc-Ag instructor Thomas McGarr and principal Harold S. Wood, with the backing of the Westport High School Committee, to promote agriculture in the town and show off the projects local vocational students had completed. The fair bought its Pine Hill Road land in 1984 and has expanded there since, to a roughly 20-acre site with its own water tower and the relocated Central Village Post Office building. It runs live entertainment, a carnival, a craft building, tractor pulls and the Saturday chicken barbecue, and its competitive side covers dairy and beef cattle, sheep, pygmy and dairy goats, rabbits and cavies, plus baking, canning, vegetable and quilting contests.
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