Massachusetts hosts 102 fall fairs and festivals from September through November 2026, including Chilmark Community Church Wednesday Flea Market, Brewster Labor Day weekend Festival of the Arts and Three County Fair. Autumn is prime fair season here — harvest fairs, agricultural shows, apple and pumpkin festivals, and the last big country fairs of the year.
Highest-rated fall events in Massachusetts
- Milton Arts and Crafts Market — Milton · Sep 27 · 5★ (15 reviews)
- Tewksbury Fall Night Out — Tawksbury · Oct 13 · 5★ (14 reviews)
- Rehoboth Fall Crafters Marketplace — Rehoboth · Oct 17 · 5★ (8 reviews)
- Salem Food Truck and Craft Beverage Festival — Salem · Sep 19–20 · 5★ (5 reviews)
- South Coast Harvest Festival — Westport · Sep 25–27 · 5★ (5 reviews)
September (45)
- Chilmark Community Church Wednesday Flea Market — Chilmark · Sep 2 · 4.7★ (3 reviews)
- Brewster Labor Day weekend Festival of the Arts — Brewster · Sep 4–6
- Three County Fair — Northampton · Sep 4–7 · 4.2★ (577 reviews)
- West Tisbury Vineyard Labor Day Artisans Festival — West Tisbury · Sep 4–6 · 4.8★ (229 reviews)
- Bridgewater End of Summer Farmers Market and Craft Fair — Bridgewater · Sep 5
- Chilmark End of Summer Flea Market — Chilmark · Sep 5
- Falmouth Harbor Craft Fair — Falmouth · Sep 5–6 · 4★ (2 reviews)
- Lee Art in the Park — Lee · Sep 5–6 · 4.5★ (2,802 reviews)
- New England Labor Day Weekend Renaissance Festival — Carver · Sep 5–7 · 3.6★ (524 reviews)
- Rutland End of Summer Makers Market — Rutland · Sep 5
- Sandwich End of Summer Fine Arts and Crafts Show — Sandwich · Sep 5
- Williamstown End of Summer Farmers Market — Williamstown · Sep 5
…and 33 more — see all September events.
October (32)
- Brewster Fall Craft Fair — Brewster · Oct 3–4
- King Richards Fall Faire — Carver · Oct 3–4
- Pepperell Fall Fest — Pepperell · Oct 3 · 4.4★ (67 reviews)
- Williamstown Fall Saturday Farmers Market — Williamstown · Oct 3
- Westford Fall Market — Westford · Oct 4 · 4.3★ (841 reviews)
- Bridgewater Fall Saturday Farmers Market and Craft Fair — Bridgewater · Oct 10
- Danvers Falliday Fun Event — Danvers · Oct 10
- Sandwich Autumn Fine Arts and Crafts Show — Sandwich · Oct 10
- Waltham Fall Craft Fair — Waltham · Oct 10 · 4.5★ (46 reviews)
- West Tisbury Vineyard Fall Artisans Festival — West Tisbury · Oct 10–11
- Williamstown Autumn Saturday Farmers Market — Williamstown · Oct 10
- Lowell Haunted Makers Market — Lowell · Oct 11 · 4.8★ (40 reviews)
…and 20 more — see all October events.
November (25)
- Leominster Fall Craft Fair — Leominster · Nov 1 · 4.3★ (845 reviews)
- Acton Handmade Harvest Market — Acton · Nov 7 · 4.5★ (77 reviews)
- Harwich Holiday Craft Fair — Harwich · Nov 7 · 4.8★ (173 reviews)
- North Adams Farmers Market — North Adams · Nov 7
- The Fall into Holidays Fair — Wilmington · Nov 7
- The FiberFest — West Springfield · Nov 7–8 · 4.5★ (9,518 reviews)
- Williamstown Holiday Farmers Market — Williamstown · Nov 7
- Woburn Bridal Affair — Woburn · Nov 8 · 2.3★ (10 reviews)
- New England Craft and Specialty Food Fair — Topsfield · Nov 13–15 · 4.3★ (2,482 reviews)
- Sandwich Fall Antique Show — Sandwich · Nov 14 · 4.5★ (99 reviews)
- West Springfield Holiday Sampler Craft Fair — West Springfield · Nov 14–15
- West Winter Fest — Plymouth · Nov 14 · 4.1★ (82 reviews)
…and 13 more — see all November events.
Frequently asked questions
How many fall festivals are in Massachusetts?
102 fall fairs and festivals take place across Massachusetts from September through November 2026.
What is the best fall fair in Massachusetts?
By Google reviews, Milton Arts and Crafts Market in Milton is among the best-rated, holding a 5★ rating from 15 reviews.
