Fair
Westport Fair 2026
3,142 views
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.
Curious what else is happening?
Other public events whose dates overlap with this one.
More Fair Events
Related Blog Posts
Written about this event
Massachusetts Fairs and Festivals in 2026: Your Complete Guide
A month-by-month guide to every major fair and festival in Massachusetts for 2026 — from small-town agricultural fairs in the Berkshires to the Big E and Topsfield Fair.
Apr 18, 2026
September 2026 Fairs in Connecticut and Massachusetts: A Weekend-by-Weekend Guide
September is the busiest month of the New England fair season, and Connecticut and Massachusetts carry most of it. Every fair and festival of the month sorted by weekend, with the two weekends still ahead marked — the Big E, Old Deerfield, Durham and more.
Sep 4, 2026
Granite State Fair 2026: The Fair Most People Still Call the Rochester Fair
The Granite State Fair, formerly the Rochester Fair, runs across two separate September weekends in 2026 — September 17-20 and September 24-27 — with the grounds closed in between. Here's what's on, and why the split schedule catches people out.
Sep 4, 2026