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9 family Halloween events near Portland, ME with 2026 dates confirmed on their official sites, across 7 towns. The earliest to open is Pumpkin Patch Trolley & Trolleyween, on September 25. 2 list free admission.
Free three-day charity pumpkin festival in Freeport with hundreds of glowing jack-o'-lanterns carved by local schools, a 5K and fun run, and a different family program each day.
No-scare Halloween day on the dunes: kids trick-or-treat along the trails, make sand art and ride a Halloween train, with the rest of the park open too.
Not-so-scary indoor Halloween for young kids: trick-or-treat stations through the museum's exhibits, pumpkin crafts, a dry ice show and a treat bag and snack to take home.
Rides on restored early-1900s trolleys out to a pumpkin patch on autumn weekends, then Trolleyween on the season's final weekend with trick-or-treat stations around the mostly outdoor museum campus.
Long-running agricultural fair north of Portland with livestock shows, a midway, harness racing, demolition derby and a giant pumpkin and squash weigh-off.
Two autumn Saturdays at the state wildlife park in Gray, with food trucks, inflatables and treats alongside the park's native Maine animals and trails.
Free three-day festival across downtown Freeport with more than 200 New England artists, makers and food producers, live music on several stages and free activities for kids.
Maine's big October agricultural fair in the western foothills, with livestock shows, pulling contests, harness racing, a carnival midway and nightly shows.
Downtown Saco's annual fall festival with a pumpkin patch, pie-eating contest, pony rides, a carnival area, live music and dozens of local vendors.
Camp Sunshine Pumpkin Festival, Cumberland Fair, Fall Fun Days at Maine Wildlife Park, Freeport Fall Festival, Fryeburg Fair, Halloween at the Desert of Maine, and 3 more. Each has its 2026 dates, hours and prices on its own page.
The earliest in this guide is Pumpkin Patch Trolley & Trolleyween on September 25, 2026.
Camp Sunshine Pumpkin Festival, Cumberland Fair, Fall Fun Days at Maine Wildlife Park, Freeport Fall Festival, Fryeburg Fair, Pumpkin Patch Trolley & Trolleyween, and 1 more are rated 1 of 5 ghosts: not scary.
Yes: Camp Sunshine Pumpkin Festival and Freeport Fall Festival list free admission on the official site.
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