September 2026 Fairs in Connecticut and Massachusetts: A Weekend-by-Weekend Guide
September is when the New England fair season is at full stretch, and Connecticut and Massachusetts carry more of it than anywhere else in the region. In a single four-week span you can get to a 100-plus-year-old agricultural fair, a one-day grange fair on a town green, an oyster festival and a garlic festival — often on the same weekend.
This is everything still ahead on our calendar for September 2026, sorted by weekend. Dates are from our event listings; for gate hours and admission prices, check each fair's own site — we don't print hours we can't source.
Labor Day weekend: September 3–7
The single biggest weekend of the Connecticut season, and it is a genuine scheduling conflict — three of the state's larger fairs run simultaneously.
Agricultural fairs
- Woodstock Fair — Sep 3–7, South Woodstock, CT
- Blandford Fair — Sep 4–7, Blandford, MA
- Spencer Fair — Sep 4–7, Spencer, MA
- Three County Fair — Sep 4–7, Northampton, MA
- Haddam Neck Fair — Sep 4–7, East Hampton, CT
- Goshen Fair — Sep 5–7, Goshen, CT
- East Middleboro 4-H Fair — Sep 5–6, Middleborough, MA
Craft and arts festivals
- Vineyard Artisans Labor Day Festival — Sep 4–6, West Tisbury, MA
- Labor Day Weekend Festival of the Arts — Sep 5–7, Brewster, MA
- Suffield on the Green Craft Fair — Sep 5–6, Suffield, CT
- Rotary Club of Falmouth Craft Fair — Sep 5–6, Falmouth, MA
- Labor Day Weekend Craft Festival — Sep 5–6, South Yarmouth, MA
- Bethel Holiday Weekend Craft Festival — Sep 5, Bethel, CT
Food and community
- Fairfield International Food Fest — Sep 5, Fairfield, CT
- Bread and Roses Heritage Festival — Sep 7, Lawrence, MA
The second weekend: September 10–13
If Labor Day weekend is the traffic jam, this is the weekend with the most variety.
Agricultural fairs
- Hebron Harvest Fair — Sep 10–13, Hebron, CT
- North Haven Fair — Sep 10–13, North Haven, CT
- Wapping Fair — Sep 10–13, South Windsor, CT
- Franklin County Fair — Sep 10–13, Greenfield, MA
- Sterling Fair — Sep 11–13, Sterling, MA
- Bethlehem Fair — Sep 11–13, Bethlehem, CT
- Ledyard Fair — Sep 11–13, Ledyard, CT
- Dartmouth Grange Fair — Sep 11–12, Dartmouth, MA
One-day grange fairs — Saturday, September 12
A cluster of small one-day town fairs all landing on the same Saturday. If you have never been to a grange fair, this is the day for it.
- Hillstown Grange Agricultural Fair — East Hartford, CT
- Granby Grange Agricultural Fair — Granby, CT
- Wallingford Grange Fair — Wallingford, CT
- Williamsburg Grange Fair — Williamsburg, MA
- Sheffield Fair — Sheffield, MA
- Norfield Grange Agricultural Fair & Market — Sep 13, Weston, CT
Festivals
- Norwalk Oyster Festival — Sep 11–13, Norwalk, CT
- Kefi Greek Festival — Sep 11–13, Norwalk, CT
- Salem Art Fair and Festival — Sep 11–13, Salem, MA
- Connecticut Maritime Heritage Festival — Sep 12–13, New London, CT
- Wethersfield CornFest — Sep 12, Wethersfield, CT
- St. Peter's Grace Apple Festival — Sep 12–13, Monroe, CT
- Brookfield Orchards Harvest Craft Fair — Sep 12–13, North Brookfield, MA
- Pride Worcester Festival — Sep 12, Worcester, MA
The third weekend: September 17–20
This is the weekend the season goes national — The Big E opens September 18 in West Springfield and runs to October 4, and Tunbridge World's Fair runs September 17–20 up in Vermont. Locally:
Agricultural fairs
- Berlin Fair — Sep 17–20, Berlin, CT
- Four Town Fair — Sep 17–20, Somers, CT
- Guilford Fair — Sep 18–20, Guilford, CT
- Orange Country Fair — Sep 19–20, Orange, CT
Craft festivals
- Old Deerfield Fall Arts & Crafts Festival — Sep 19–20, Deerfield, MA
- Fruitlands Craft Festival — Sep 19–20, Harvard, MA
- Townsend Arts & Crafts Fair — Sep 19–20, Townsend, MA
- Chatham Fall Craft Festival — Sep 17, Chatham, MA
Festivals
- Olde Mistick Village Garlic Festival — Sep 19–20, Mystic, CT
- Cheshire-Prospect Fall Festival — Sep 18–19, Cheshire, CT
- Seymour Pumpkin Festival — Sep 20, Seymour, CT
- Harwich Cranberry Arts & Music Festival — Sep 20, Harwich, MA
- Bloomfield Food Truck Festival — Sep 19–20, Bloomfield, CT
The last weekend: September 24–27
- Durham Fair — Sep 24–27, Durham, CT. Connecticut's largest.
- Belchertown Fair — Sep 25–27, Belchertown, MA
- Bristol Mum Festival — Sep 25–27, Bristol, CT
- Milford Oktoberfest — Sep 25–26, Milford, CT
- Stafford AppleFest — Sep 26, Stafford Springs, CT
- Celebrate Mansfield Festival — Sep 26–27, Storrs, CT
- Trumbull Arts Festival — Sep 27, Trumbull, CT
- Peabody International Festival — Sep 27, Peabody, MA
Running all month
Two long-run events overlap most of the above:
- Connecticut Renaissance Faire — through Oct 25, Lebanon, CT
- King Richard's Faire — through Oct 25, Carver, MA
Q: What fairs are on in Connecticut over Labor Day weekend 2026?
Three of Connecticut's larger agricultural fairs run simultaneously: the Woodstock Fair (Sep 3–7), Haddam Neck Fair (Sep 4–7) and Goshen Fair (Sep 5–7), plus a number of craft festivals. Just over the Massachusetts line, Blandford, Spencer and Three County Fairs all run Sep 4–7.
Q: When is the Durham Fair in 2026?
The Durham Fair runs Thursday, September 24 through Sunday, September 27, 2026, in Durham, Connecticut. It is the largest fair in the state.
Q: What is a grange fair?
A grange fair is a small agricultural fair run by a local Grange chapter, usually lasting a single day on a town green or grange hall grounds. Several run on Saturday, September 12, 2026, including Hillstown, Granby and Wallingford in Connecticut and Williamsburg in Massachusetts.
Q: Are there still craft fairs accepting vendors in September?
Application windows vary by event and are handled by each organizer directly. Our Massachusetts and Connecticut craft fair guides cover the application calendar, and each event listing links through to the organizer.
Related Reading
- Connecticut Fairs & Festivals 2026: Your Complete Guide
- Massachusetts Fairs & Festivals in 2026
- Durham Fair 2026: A Visitor's Guide to Connecticut's Largest Fair
- Hebron Harvest Fair 2026 Visitor's Guide
- Belchertown Fair 2026: A Visitor's Guide
- Old Deerfield Craft Fairs: Vendors and Visitors Guide
- Craft Fairs in Massachusetts 2026
Last updated: September 2026
