Massachusetts Fairs and Festivals in 2026: Your Complete Guide

Massachusetts has one of the richest fair traditions in New England. From small-town agricultural fairs in the Berkshires to the legendary Big E in West Springfield — the largest fair in the northeast — the state offers something for every kind of fairgoer from midsummer through fall.

This guide covers the major Massachusetts fairs and festivals happening in 2026, organized by month. Whether you're looking for livestock shows and tractor pulls, craft beer and fried dough, or handmade goods and live music, there's a fair within driving distance of wherever you are in the state.

Summer Fairs (July – August)

Fair season in Massachusetts starts in mid-July and ramps up quickly through August. The western half of the state leads the way, with small agricultural fairs that feel more like Vermont than Boston.

July

The Westport Fair (July 15–19) near the Rhode Island border is a classic agricultural fair with oxen pulls, horse shows, and a packed midway. On the same weekend, the Hampshire County 4-H Fair (July 18) in Cummington gives families a small, welcoming introduction to the fair circuit. The month wraps with the Barnstable County Fair (July 20–25) on Cape Cod — one of the few fairs in the state where you can smell salt air from the midway — and the Hampden County 4-H Fair (July 25) on the Big E grounds.

August

August is peak fair month in Massachusetts. The Bolton Fair (August 14–16) in central Massachusetts is a local favorite — a traditional agricultural fair with demolition derbies, baking competitions, and a strong 4-H presence. The nearby Middlefield Fair (August 14–16) and Martha's Vineyard Fair (August 13–16) run the same weekend, giving you options from the Berkshires to the islands.

Later in August, the Littleville Fair (August 7–9), Heath Fair (August 21–23), Westfield Fair (August 21–23), and Hardwick Fair (August 21–23) all compete for your weekend. The massive Marshfield Fair (August 21–30) runs for ten days on the South Shore and draws some of the biggest crowds in the state.

The month closes with the Cummington Fair (August 27–30), the Shelburne Grange Fair (August 29), the 3 County Fair in Northampton (August 29), and the Middlesex County 4-H Fair (August 28–30).

Fall Fairs (September – October)

September and October bring the biggest events of the year, with cooler weather, foliage, and the state's marquee fairs.

September

Labor Day weekend features the Blandford Fair (September 4–7) in the Hilltowns and the Spencer Fair (September 4–7) in central Massachusetts. The Spencer Fair is one of the state's largest, with a packed midway, harness racing, and a demolition derby that regularly sells out.

Mid-September brings the Sterling Fair (September 11–13), the 177th Franklin County Fair in Greenfield (September 10–14), and the Belchertown Fair (September 25–27). The Belchertown Fair is a gem — a true community fair with agricultural exhibits, a parade, and an old-fashioned atmosphere that bigger fairs have lost. Read our full Belchertown Fair guide for details on what to see and how to plan your visit.

October

The Topsfield Fair (October 2–12) is the state's oldest continuously running agricultural fair, dating back to 1818. Ten days of competitions, food, rides, and the famous giant pumpkin weigh-off make this the premier Massachusetts fair outside of the Big E.

And speaking of the Big E — the Eastern States Exposition takes over West Springfield for 17 days in September and October. It's technically a multi-state fair representing all six New England states, but it's on Massachusetts soil and no Massachusetts fair guide would be complete without it. For tips on navigating the Big E, see our complete Big E guide, food guide, and budget guide.

Craft Fairs and Specialty Events

Beyond traditional agricultural fairs, Massachusetts hosts excellent craft fairs and arts festivals throughout the year.

The Old Deerfield Craft Fairs run three shows annually at Old Deerfield and the Eastern States Exposition grounds — a Spring Sampler (March 7–8), a Fall Festival (September 19–20), and a Holiday Sampler (November 7–8). These are juried craft shows with high-quality artisans and make excellent alternatives to the agricultural fair circuit.

The Brookline Village Arts Festival (May 2), South Shore Arts Festival in Cohasset (June 20–21), and Coolidge Corner Arts Festival (June 6) bring art and craft fairs to the Boston metro area.

Planning Your Massachusetts Fair Season

Massachusetts fairs cluster heavily in August and September. If you're trying to hit several, plan around geography — the western Massachusetts fairs (Cummington, Blandford, Heath, Shelburne) are all within an hour of each other, making a Berkshires fair weekend easy to plan. The central Massachusetts fairs (Bolton, Spencer, Sterling, Hardwick) are similarly clustered.

For tips on making the most of fair season across the region, check out our New England fair road trip guide, our guide to what to wear to a fair, and the New England fair food bucket list. Families should also look at our picks for the best New England fairs for kids.

If you're a vendor looking to set up at Massachusetts fairs, start with our beginner's guide to becoming a craft fair vendor.