12 upcoming listings — live music, theater, markets, drag, comedy and more, each with a time, a venue and a street address.
What's coming up
Pumpkinboat Building Sat 10 Oct 2026, 9:00 AM — Meetup Downtown Damariscotta (Pumpkinfest & Regatta) · 40 Main St, Damariscotta, ME 04543 · Free
Pumpkinfest Kid's Zone Sat 10 Oct 2026, 10:00 AM — Meetup Downtown Damariscotta (Pumpkinfest & Regatta) · 40 Main St, Damariscotta, ME 04543 · Free
Pumpkinfest Dessert Contest Sat 10 Oct 2026, 10:00 AM — Festival Downtown Damariscotta (Pumpkinfest & Regatta) · 40 Main St, Damariscotta, ME 04543 · Free
Pumpkinfest Buskers Sat 10 Oct 2026, 11:00 AM — Live music Downtown Damariscotta (Pumpkinfest & Regatta) · 40 Main St, Damariscotta, ME 04543 · Free
Giant Pumpkin Parade Sat 10 Oct 2026, 2:00 PM — Festival Downtown Damariscotta (Pumpkinfest & Regatta) · 40 Main St, Damariscotta, ME 04543 · Free
Pumpkin Derby Sun 11 Oct 2026, 9:00 AM — Festival Downtown Damariscotta (Pumpkinfest & Regatta) · 40 Main St, Damariscotta, ME 04543 · Free
Mr. Drew and His Animals Too Sun 11 Oct 2026, 11:00 AM — Meetup Downtown Damariscotta (Pumpkinfest & Regatta) · 40 Main St, Damariscotta, ME 04543 · Free
Pumpkinboat Regatta Sun 11 Oct 2026, 12:00 PM — Sports Downtown Damariscotta (Pumpkinfest & Regatta) · 40 Main St, Damariscotta, ME 04543 · Free
Pumpkinfest Pie-Eating Contest Sun 11 Oct 2026, 3:00 PM — Festival Downtown Damariscotta (Pumpkinfest & Regatta) · 40 Main St, Damariscotta, ME 04543 · Free
Tour de Gourd 5K and Walk Mon 12 Oct 2026, 8:00 AM — Fitness Downtown Damariscotta (Pumpkinfest & Regatta) · 40 Main St, Damariscotta, ME 04543 · Free
The Pumpkin Drop Mon 12 Oct 2026, 11:00 AM — Festival Downtown Damariscotta (Pumpkinfest & Regatta) · 40 Main St, Damariscotta, ME 04543 · Free
Kids' Free Movie Matinee: Minions - The Rise of Gru Mon 12 Oct 2026, 2:00 PM — Live show Downtown Damariscotta (Pumpkinfest & Regatta) · 40 Main St, Damariscotta, ME 04543 · Free
Listings are seeded from venue and organiser calendars. See them on the map.