Featured
Events
The fun never stops in Greater Portland!
From daily tours to cruises, art exhibitions, music, and live performances.
Events with ongoing dates appear at the top, keep scrolling for new events.
Always cross-check event time/date with organizer’s website before booking.
27
Sep
through
5
Oct
Fryeburg Fair
Fryeburg
Maine’s largest agricultural fair. Beautiful setting in prime foliage season.…
2
Oct
Puerto Rican Wine Dinner at Angoor
Portland
Presented by Angoor Wine Bar
Join us for our PUERTO RICAN Wine Dinner, Puerto Rican…
2
Oct
Reconstruction’s Spirits
Portland
Presented by Victoria Mansion
New Orleans Séances, Afro-Creole Mediums, and the Battle for Equality
3‐5
Oct
Freeport Fall Festival
Freeport
Presented by Visit Freeport
Town-wide, three days – the best of New England artists & makers!
3
Oct
October First Friday Art Walk
Portland
Presented by Maine Historical Society
Visit the Maine Historical Society galleries after hours for free…
3
Oct
ArtsFest at USM
Portland
Presented by University of Southern Maine
Join us on October 3, 2025, for a day of…
4
Oct
Fall Fun Day
Gray
Presented by Maine Wildlife Park
View moose, bears, & more! Face painting, scavenger hunts, food trucks