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- This Weekend's Events In Portland Maine: Sep 21 - 24
This Weekend's Events In Portland Maine: Sep 21 - 24
Fall Festivals Across Maine, Oktoberfest At Foundation brewing, and more!

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Today’s Forecast
🌤️ Few clouds | 73° | Sunset: 6:40 PM
Highlight: Fall Festivals In Maine

This week officially kicks off Fall in Maine, and that means the start of Fall Festival season! Every weekend from September through October, you will see Harvest Festivals, Oktoberfests, Community Celebrations, and more going on across the state.
We’ve compiled a few of the major festivals here at Hello Portland, so keep these on the radar as you’re looking for weekend plans!
Mahoosuc Adventure Fest | Sunday River | Sep 22 - 24
Pemaquid Oyster Festival | Pemaquid | Sep 24
Maine Artisan Fest | Sunday River | Sep 29 - October 1
Fryeburg Fair | Fryeburg | Oct 1 - 8
Freeport Fall Festival | Freeport | Oct 6 - 8
Sunday River Fall Festival | Sunday River | October 7 - 8
York HarvestFest | York | Oct 14
Kennebunk HarvestFest | Kennebunk | Oct 15
Ogunquitfest | Ogunquit | Oct 20 - 22
Harvest On the Harbor | Portland | Oct 25
Halloween in Kennebunks | Kennebunk | Oct 31
Events This Week
Thursday, September 21 | 🌤️ | 73°
🎹 Dueling Pianos Summer Concert | Shipyard Brewing Company | Portland, ME | 5:30 PM | Epic musical showdown at Shipyard with Dueling Pianos Summer Concert.
🥁 Fall Equinox Drumming Circle & Autumnal Qi Gong | Westbrook Common | Westbrook, ME | 5:00 PM | Celebrate Fall Equinox with drumming, Qi Gong, and community gathering!
🎞️ Barbie & Mean Girls at Saco Drive-in | The Saco Drive-In | Saco, ME | 7:45 PM | Barbie & Mean Girls event: Gate opens 6:30pm; Show starts 7:45pm.
Friday, September 22 | 🌤️ | 68°
🎵 The Happy Fits: Under The Shade Of Green | State Theatre | Portland, ME | 7:00 PM | Indie rock band The Happy Fits formed Pittstown, New Jersey is playing at the State Theater.
🍂 Hurricane Meadows Fall Festival | Wilshore Farms | Falmouth, ME | Fri-Sun @ 10 AM - 6 PM | Pumpkin patches, corn mazes, and a potato cannon; what more could you ask for?
🎭 What We Get To Keep | The Hill Arts | Portland, ME | 7:00 PM | Tragic play explores loss, secrets, and the power of memory.
Saturday, September 23 | 🌧️ | 65°
🍺 Oktoberfest @ Foundation Brewing | Foundation Brewing | Portland, ME | 12 - 8 PM | Food specials and a stein hoisting contest at 3pm. Lederhosen and Dirndls not required but encouraged!
📘 4th Annual Beautiful Blackbird Children's Book Festival | Children's Museum & Theatre of Maine | Portland, ME | 9:30AM - 3PM | A celebration of children’s book authors and illustrators of the African Diaspora
🎭 The Maine Stage: Burlesque, Drag, Flow | Mayo Street Arts | Portland, ME | 7:00 PM | Maine showcases top talent in Burlesque, Drag, and Flow performances.
⚾ Northeast Sports Card Expo: Portland, Maine | James A Banks Sr Exposition Building | Portland, ME | 9:00 AM
Sunday, September 24 | 🌧️ | 68°
🎃 Cumberland Fair Kickoff | Cumberland Fairgrounds | Cumberland, ME | 4:30 PM | Joyful gathering with food, friends, and family.
🎨 Fete Market @ Austin Street | Austin Street Brewery | Portland, ME | 1:00 PM | Fête Market is a free, curated, pop-up experience with a laid back, block party vibe
🎥 Silent Movie Sunday | Congress Square Park | Portland, ME | 10:30 PM | Experience classic silent movies on 16mm film with live music.
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🏥 Health
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🦞 Local
About the Authors
Hello Portland was started by Mike Warren and Madison Hopkins. Mike is a Computer Science student at the Roux Institute and Madison just started her residency at Maine Medical Center.
Upon our recent move to Portland in June 2023, we eagerly set out to explore the city’s vibrant scene. However, we struggled to find events in Maine that truly resonated with our interests. That’s why we decided to create Hello Portland - not just for our benefit, but with the hope that it helps you discover exciting activities that you might have missed otherwise. We hope you enjoy it!
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