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Fall and Halloween Events and Fairs in the Portland Area

By Kristina Wilson, Macaroni KID Portland August 24, 2022

The Portland area has TONS of fun and family-friendly Fall and Halloween events and fairs that are not to be missed! From County Fairs to Pumpkin Trains, we've got you covered with our list of Portland area Fall and Halloween events and fairs.  Find a list of events coming up this fall and a link for more information. 

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Fall and Halloween Festivals and Events


2 HOUR FARM PASS WITH CORN MAZE
August 19 - October 31


Sunflower Festival 
September 3,4,5,10,11


Fall Frolic Festival
September 17


Pumpkin Patch Trolley
September 23,24,25,30 October 1,2,7,8,9,10,14,15,16


Pumpkin Valley Farm Fall Festival
Open Saturdays and Sundays from September 24-October 30


Community Friendly Connection Fall Fest
September 24


Cumberland Fair
September 25-October 1


Freeport Fall Festival
September 30-October 2


Wells Harbor 13th Annual Family Jamboree
October 1


The Fryeburg Fair
October 2-9


Saco Main Street Pumpkin Harvest Festival
October 22


Pumpkin Train
October 22,23,29,30


Happy Trolleyween!
October 28-30


Little Monsters Ball
October 29