Massachusetts Fairs & Festivals in September 2026

40 upcoming events. Everything on the calendar for September 2026.

Showing 10 of 40 events

Photo of Old Deerfield Fall Arts & Crafts Festival event

Old Deerfield Fall Arts & Crafts Festival

Sat, Sep 19, 2026 - Sun, Sep 20, 2026

Old Deerfield, Deerfield, MA

Festival illustration

Cape Cod Brew Fest

Sat, Sep 19, 2026

Cape Cod Fairgrounds, Falmouth, MA

FestivalBeer Festival

Gun Show illustration

Marlborough Gun Show - September 2026

Sat, Sep 19, 2026

Best Western Royal Plaza Trade Center, Marlborough, MA

Gun ShowTrade Show

Event illustration

Harwich Cranberry Arts & Music Festival 2026

Sun, Sep 20, 2026

Harwich Community Center, Harwich, MA

Art Show illustration

stART on the Street Fall 2026

Sun, Sep 20, 2026

Park Avenue (Worcester), Worcester, MA

Art ShowCraft FairFestival

Photo of Fall Fest Vinyl Record Show — Dedham 2026 event

Fall Fest Vinyl Record Show — Dedham 2026

Sun, Sep 20, 2026

Holiday Inn Dedham, Dedham, MA

Trade ShowFlea Market

Flea Market illustration

Harry's Model & Die-Cast Show — Franklin (September 2026)

Sun, Sep 20, 2026

Franklin Elks Lodge, Franklin, MA

Flea MarketTrade Show

Photo of Belchertown Fair 2026 — Sep 25–27 in Belchertown, MA event

Belchertown Fair 2026 — Sep 25–27 in Belchertown, MA

Fri, Sep 25, 2026 - Sun, Sep 27, 2026

Belchertown Fair, Belchertown, MA

Photo of NorthEast Comic Con & Collectibles Extravaganza — September 2026 event

NorthEast Comic Con & Collectibles Extravaganza — September 2026

Sat, Sep 26, 2026 - Sun, Sep 27, 2026

Boxboro Regency Hotel & Conference Center, Boxborough, MA

Comic ConPop Culture Convention

Harvest Festival illustration

Soule Homestead Harvest Fair 2026

Sat, Sep 26, 2026

Soule Homestead Education Center, Middleborough, MA

Harvest FestivalFestivalCraft Fair

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