Damariscotta’s PumpkinFest, Portland’s Harvest on the Harbor and western Maine scenic drives anchor a month of autumn events stretching into November KEY TAKEAWAYS Damariscotta PumpkinFest & Regatta runs October 9–12, 2026, with giant pumpkin art, races, contests and the signature pumpkin-boat regatta. Harvest on the Harbor returns to Portland October 15–17, featuring the Maine Lobster… Read the full news article
Maine turns October into a festival season of pumpkin boats, coastal food and peak foliage
