Events Calendar

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Events

The fun never stops in Greater Portland!

From daily tours to cruises, art exhibitions, music, and live performances.

Events with ongoing dates appear at the top, keep scrolling for new events.

Always cross-check event time/date with organizer’s website before booking.

Ferris Wheel. Photo credit: Serena Folding
27
Sep
through
5
Oct
Fryeburg Fair
Fryeburg

Maine’s largest agricultural fair. Beautiful setting in prime foliage season.…
Girls Night at Angoor. Photo Provided by Angoor Wine Bar
2
Oct
Puerto Rican Wine Dinner at Angoor
Portland
Presented by Angoor Wine Bar

Join us for our PUERTO RICAN Wine Dinner, Puerto Rican…
Photo Courtesy of Victoria Mansion
2
Oct
Reconstruction’s Spirits
Portland
Presented by Victoria Mansion

New Orleans Séances, Afro-Creole Mediums, and the Battle for Equality
Freeport Fall Festival - Photo Credit: Visit Freeport
3‐5
Oct
Freeport Fall Festival
Freeport
Presented by Visit Freeport

Town-wide, three days – the best of New England artists & makers!

photo by Abigail Jakub
3
Oct
October First Friday Art Walk
Portland
Presented by Maine Historical Society

Visit the Maine Historical Society galleries after hours for free…
Crewe Center photo courtesy of University of Southern Maine
3
Oct
ArtsFest at USM
Portland
Presented by University of Southern Maine

Join us on October 3, 2025, for a day of…
Fall Fun Day - Photo Credit: Maine Department of Inland Fisheries and Wildlife
4
Oct
Fall Fun Day
Gray
Presented by Maine Wildlife Park

View moose, bears, & more! Face painting, scavenger hunts, food trucks

Upcoming Events (8 total)

28
Nov
through
13
Dec
Merry Madness Shopping Crawl
Presented by Portland Downtown

This magical winter shopping crawl through downtown Portland, ME returns December 7th.
5‐13
Dec
Sparkle Celebration
Presented by Visit Freeport

Full week of holiday festivities in Freeport, Maine!
5‐14
Dec
Christmas Prelude Trolley
Kennebunkport
Presented by Seashore Trolley Museum

Christmas Prelude Trolley Rides!
16
Dec
‘A Victorian Nutcracker’
Portland
Presented by Portland Ballet

Portland Ballet presents 'A Victorian Nutcracker'
20
Dec
‘A Victorian Nutcracker’
Westbrook
Presented by Portland Ballet

Portland Ballet presents 'A Victorian Nutcracker'
21
Dec
‘A Victorian Nutcracker’
Westbrook
Presented by Portland Ballet

Portland Ballet presents 'A Victorian Nutcracker'
21
Dec
‘A Very Nutty Nutcracker’
Westbrook
Presented by Portland Ballet

Portland Ballet presents 'A Very Nutty Nutcracker'
23
Dec
Christmas with Kennerley
Portland
Presented by Friends of the Kotzschmar Organ

Home for the Holidays: A Festive Evening with Kennerley & Friends

Ongoing Events (5 total)

26
Oct
through
7
Feb
Goat Yoga – Cold Weather Style
Westbrook
Presented by Ashley Flowers Yoga

Come cozy up with goats for a heartwarming outdoor yoga experience!
15
Nov
through
23
Dec
The Polar Express Train Ride
Portland
Presented by Maine Narrow Gauge Railroad Co. & Museum

The Polar Express™ Train Ride is the largest annual fundraiser…
15
Nov
through
21
Dec
Magic Awaits! Gardens Aglow
Boothbay
Presented by Coastal Maine Botanical Gardens

Experience Nature in Motion at Gardens Aglow and see the…
30
Nov
through
31
Dec
Holidays on the Rocks
Westbrook
Presented by Rock Row

Get in the holiday spirit at Rock Row with our Holiday on the Rocks, month long events!
22
Mar
Bach Birthday Bash
Portland
Presented by Friends of the Kotzschmar Organ

Celebrate Bach: Timeless Music for All with James Kennerley
...