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Fall in Maine is more than just colorful leaves and cozy sweaters—it’s also the season for some of the best festivals around.

From local fairs to harvest celebrations, Maine has a fall festival for everyone.

Whether you’re a foodie, a craft lover, or just looking for some good old-fashioned fun, this guide will help you find the perfect event in 2024.

Maine’s Fall Festivals

1. Fryeburg Fair

Dates: Sept 27th – Oct 5th, 2025

This agricultural fair started in 1851 and is Maine’s largest, and second only to the Eastern States Fair in Massachusetts. 

In 2025, the fair takes place from September 27 to October 5th!

With everything from horse racing and livestock shows to a huge midway with rides and games, there’s something for everyone.

And let’s not forget the food—fried dough, lobster rolls, and homemade pies are just the beginning.

If you love old-fashioned fun, this is the fair for you.

2. Acadia’s Oktoberfest

Dates: October 10th to 11th 2025

If you’re a fan of craft beer and fall festivities, Acadia’s Oktoberfest in Southwest Harbor is where you’ll want to be.

This annual event brings together local breweries, wineries, and food vendors for a day of tastings and fun.

There’s also live music, crafts, and a wine-tasting tent. It’s the perfect way to enjoy the flavors of fall with a view of Acadia National Park in the background.

Acadia is one of my favorite places to visit in Maine. Read my 20 Best Things To Do In Acadia National Park.

Here are my picks for The Most Delicious Lobster Rolls Near Acadia National Park!

3. Freeport Fall Festival

Dates: October 3rd to 5th

Each year on the first weekend in October, Visit Freeport brings together over 175 artists, makers, and local food producers for three days of festivities. 

If you love shopping, the Freeport Fall Festival is for you!

You’ll find everything from handmade jewelry and pottery to paintings and woodwork.

There’s also live music, local food vendors, and activities for kids.

It’s the perfect spot to pick up unique gifts while enjoying the fall weather.

4. Damariscotta Pumpkinfest & Regatta

Dates: October 10th to 13th

Looking for something a little quirky? Check out the Pumpkinfest & Regatta in Damariscotta.

This unique festival is all about pumpkins—giant pumpkins, to be exact.

You’ll see massive pumpkins carved into boats and raced down the river, plus pumpkin-themed activities, a parade, and more.

It’s a fun, family-friendly event that celebrates the weird and wonderful side of fall.

The 2025 festival is shaping up to be another fun-filled weekend.

5. Sunday River Fall Festival

Dates: October 11th to 12th

The Sunday River Fall Festival is a weekend full of outdoor fun and entertainment.

Held at the Sunday River Resort, this event features everything from a chili cook-off to a beer garden with live music.

You can also take a scenic chairlift ride to enjoy the stunning fall foliage.

If you’re into adventure, try the North American Wife Carrying Championship—it’s a hilarious and competitive event that’s sure to entertain.

This festival will take place at Sunday River Ski Resort in Newry from October 11-12, 2025.

6. Portland’s Harvest on the Harbor

Dates: October 30th to November 1st

Foodies, this one’s for you! Harvest on the Harbor in Portland is a celebration of Maine’s best food and drink.

This multi-day event includes tastings, cooking competitions, and chef demos, all showcasing the local culinary scene.

From fresh seafood to craft cocktails, you’ll get to sample some of the best flavors Maine has to offer.

It’s a great way to enjoy the fall season while indulging in delicious eats.

The festival takes place this year from October 30th to November 1st, 2025!

If you are a foodie visiting Portland, check out my The Ultimate Self-Guided Food Tour of Portland, Maine: By A Local!

7. York Harvestfest

Date: October 19th

York HarvestFest is a great way to celebrate fall with the whole family.

Held at York Beach, this festival includes a full day of live music, local food vendors, and over 150 craft and art booths.

Kids will love the special Kidsfest area, which features games, rides, and activities just for them.

The festival also includes a variety of demonstrations, from pumpkin carving to cooking, making it a fun and educational experience.

This festival will take place at Short Sands Beach in York Beach!

8. OgunquitFest

Date: October 24th to 26th

The event generally showcases 60+ vendors, most local to New England.

Craft fairs typically include a wide variety of jewelry, handmade candles, local treats, custom soaps, foods, and much much more!

Visit the heart of beautiful Ogunquit for our OgunquitFest Artisan Craft Fair this October 24-26, 2024!

9. Boothbay Fall Foliage Festival

Date: October 11th to 12th

The Fall Foliage Festival in Boothbay has been a family tradition in Mid Coast, Maine, for the past 55 years.

Featuring dozens of vendor booths, fabulous entertainment, live music, and delicious Fall foods.

Held at the Boothbay Railway Village, this festival features a mix of arts and crafts vendors, live music, and delicious local food.

You can also enjoy antique car displays and train rides through the scenic countryside.

The festival is a great way to soak in the fall colors while enjoying some classic Maine culture.

If you are visiting Boothbay, you have to check out Boothbay Lobster Wharf: The Best Seafood Spot With Views!

For cocktails, head over to This Boothbay Speakeasy Has The Best Cocktails In Maine

Explore More Of Maine

As you can see, there are so many amazing things to do this fall in Maine!

Make sure to read my Ultimate Guide to Maine’s Fall Foliage: When and Where to Go.

For my favorite fall hike in the state, check out Haystack Mountain: Fall Foliage, Trail Details & Tips!

If you want to take a full New England Fall Foliage road trip, you can! Here are The Best Spots For New Hampshire Fall Foliage!

Don’t forget to check out my favorite lobster shacks in Maine! A Local’s Guide To The Best Lobster Rolls In Maine!