Portland Maine Events October 2025. Browse our events calendar and save your favorites. Run with us sunday, october 5, 2025, 7:45 a.m.

Let’s take a journey through some of the best fairs and festivals that make fall in maine truly special. You’re in for an incredible wine education experience as you sail through beautiful casco bay, in maine’s most colorful season, with scenic views of maine lighthouses, islands, and waterways, and fall foliage colors in the backdrop.