October News – Damariscotta PumpkinFest & Regatta and Harvest on the Harbor

Damariscotta PumpkinFest & Regatta

Maine’s quirkiest fall festival is the Damariscotta Pumpkinfest & Regatta, held October 9 to 12, 2026 on Indigenous Peoples’ Day Holiday Weekend. The festival features pumpkin weigh-offs, local artists transforming pumpkins into works of art which are on display throughout the village center, a parade, a pumpkin dessert contest, a pumpkin soapbox-style race, and a pie-eating contest. The highlight is the Pumpkin Boat Regatta, when costumed captains pilot 400-700-pound hollowed-out pumpkins down the river, racing one another in Damariscotta Harbor. Monday brings a pumpkin drop to end the festivities.

Harvest on the Harbor

Harvest on the Harbor returns from October 15 to 17, 2026, celebrating the best of Maine food, drink, and Maine-maker events. Highlights include The Maine Lobster Chef of the Year Competition and two sessions of the Maine OysterFest with the Maine Oyster Company, with Maine’s best oysters, drinks, and live music. 

Bar Harbor Ghost Tours

Settle into spooky season with Bar Harbor Ghost Tours, which created the original Bar Harbor Ghost Tour and the Haunted Mansion Tour and has been lauded by USA Today. What really sets this company apart is that it’s Indigenous-owned and operated, weaving local Indigenous stories from Maine’s Wabanaki tribes into the tour.

Grafton Notch Scenic Byway

Maine’s National and State Scenic Byways are a collection of picturesque driving tours throughout the state. As western Maine enters peak foliage season (see Maine’s official fall foliage site for more details), plan a fall road trip along Grafton Notch Scenic Byway for stunning vistas of orange-hued mountains set against striking blue lakes and rivers. Your route follows the Bear River through the Mahoosuc range up to the New Hampshire border; as you return to Newry, continue down Route 2 to Bethel for a taste of one of Maine’s up-and-coming stars of the culinary scene.

On Deck in November

Downeast Cider + Cheese Festival: The Downeast Cider + Cheese Festival in Ellsworth on November 13 and 14, 2026 celebrates Maine’s cider and cheese makers and the agricultural traditions behind their work. Cider once played an important role in the local economy and was shipped far beyond the region; learn about apple heritage and enjoy a curated tasting of ciders and cheeses.

Gardens Aglow: One of Maine’s most spectacular holiday events returns in November. Gardens Aglow is an annual festival of lights at the Coastal Maine Botanical Gardens in Boothbay. At nearly 325 acres, the Coastal Maine Botanical Gardens is New England’s largest public garden, with close to a mile of saltwater frontage. Inspired by nature’s cycles, this year’s Gardens Aglow theme, “Gathered In Maine,” is a “glowing” journey through the seasonal traditions, landscapes, and natural connections that bring us together. The garden has more than 750,000 LED lights strung among its gardens, offering the largest light display in the state. This year’s Gardens Aglow runs from November 14, 2026 through January 2, 2027.