October 2026 Fairs & Festivals in Maine
4 events happening across the state in October 2026.
AgriculturalFamily
Cumberland Fair
Greater Portland's agricultural fair, $15 gate, late September into October.
Sep 27 – Oct 3Cumberland
ArtisanCraftSeasonal
Freeport Fall Festival
27th annual juried arts and crafts festival in downtown Freeport.
Fri–Sun, Oct 2–4Freeport
AgriculturalFamily
Fryeburg Fair
Maine's largest fair, October 4-11, $15 gate, children under 12 free.
Oct 4–11Fryeburg
SeasonalFamilyArtisan
Damariscotta Pumpkinfest & Regatta
Giant pumpkin festival and pumpkin-boat regatta in Damariscotta.
Oct 9–12Damariscotta