10 Maine fall events
worth the drive.
Maine's biggest fair, a river regatta raced in carved pumpkins, and thousands of lit jack-o'-lanterns on the L.L.Bean campus. Beyond Boothbay Harbor, this is what we'd put on the calendar.
All 10, at a glance.
| Event | Where | 2026 dates | Admission |
|---|---|---|---|
| Livermore Falls Apple Pumpkin Festival | Livermore Falls | Sep 26 | Free |
| Common Ground Country Fair | Unity | Sep 25–27 | Free 12 & under; ~$15–20 adult |
| Cumberland Fair | Cumberland | Sep 27–Oct 3 | Gate fee, check site |
| Freeport Fall Festival | Downtown Freeport | Oct 2–4 | Free |
| Fryeburg Fair | Fryeburg | Oct 4–11 | $15 adult, free under 12 |
| Damariscotta Pumpkinfest & Regatta | Damariscotta | Oct 9–12 | Free |
| Shaker Hill Apple Festival | Alfred | Mid-September weekend | Free |
| Camp Sunshine Pumpkin Festival | Freeport (L.L.Bean campus) | Oct 16–18 | Free (benefit) |
| Saco Pumpkin Harvest Festival | Saco | Oct 24 | Free |
| Great Maine Apple Day | Unity | Late October (weekday) | By donation |
Dates as published on each event's own site as of September 2026. Confirm before you go; Shaker Hill's exact 2026 date was not yet posted at the time of writing.
Which Maine fall events are best for young kids?
The Camp Sunshine Pumpkin Festival is the most magical: thousands of lit jack-o'-lanterns across L.L.Bean's paved, stroller-friendly campus, and it benefits a real charity. Damariscotta Pumpkinfest is the most photogenic, with giant pumpkins raced as boats down the river, and it's a short drive from Boothbay Harbor for a weekend that combines both. Common Ground Country Fair is the calmest option: no cars in the main lot, a free shuttle, and a low-stimulation pace compared to a midway fair.
What families ask us.
What are the best fall festivals in Maine in 2026?
Ten real, dated events, from the Fryeburg Fair, Maine's biggest agricultural fair, in early October through Great Maine Apple Day in late October. The Fryeburg Fair and the Camp Sunshine Pumpkin Festival have the broadest family appeal.
Which Maine fall festivals are free?
Damariscotta Pumpkinfest, the Saco Pumpkin Harvest Festival, the Freeport Fall Festival, the Camp Sunshine Pumpkin Festival, and the Livermore Falls Apple Pumpkin Festival don't charge admission. The Fryeburg Fair, Cumberland Fair and Common Ground Country Fair all charge a gate fee.
Is there a fall event near Boothbay Harbor?
Damariscotta Pumpkinfest & Regatta is the closest match, a short drive from Boothbay Harbor, where giant pumpkins are carved and raced as boats on the river. It pairs naturally with a Boothbay Harbor weekend.
Do dates for these events change year to year?
Yes, especially the smaller town festivals. Confirm the date and hours on each event's own site before you go.
When is the best time to see fall foliage in Maine?
Northern and western Maine usually peak in late September into early October, and the Midcoast around Boothbay Harbor peaks in the first two weeks of October. That lines up well with the Fryeburg Fair and Damariscotta Pumpkinfest. Our New England fall guide has the full peak-by-region table, and Maine with kids covers Portland and Acadia.