Top 10 Festivals In Portland, Maine

festivals in portland maine
Irene
Irene 
Updated
| 5 min read

It might be a tiny city but the sophisticated, coastal Portland is the perfect destination for your vacation. The city is a tourist magnet attracting even the most elite including actors, musicians, and artists. Portland, Maine has got so much to offer. You can choose to stroll through the lively Portland harbour, explore Portland’s museums, or have fun on the water. It is undeniable that there is plenty to enjoy in Portland, Maine, you may even get confused on what to do, but one activity you cannot afford to miss out on is attending the festivals. Check out some of the best festivals in Portland, Maine.

1. Art in the Park

Editor's Note: Photo taken from the establishment's official social account

Posted by South Portland Art in the Park on Wednesday, August 18, 2021

Held every August at Mill Creek Park, Art in the Park is arguably the best summer event in Portland. The events host more than 175 artists who are always eager to show off their stunning art. The event also has a food court where you will find both local and international meals, a safe play area for the kids, and live music performances in the afternoon. You can bring along your child and watch them polish their skills at the Kids in the Park area where they will get to display their works. The atmosphere of the festival, the music, and the fun activities for the kids make Art in the Park the best activity to indulge in with your family.

Art in the Park

Address: Millcreek Park South Portland, Maine

Website: Art in the Park

Takes place: August

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2. Portland Harvest Festival [Last event in 2019]

Posted by Portland Harvest Festival on Thursday, 3 October 2019

Held every September, Portland Harvest Festival is a festival that is dedicated to supporting local families. At the festival, you will get to enjoy countless fun activities including taking family photos, horseback riding, games, and giveaways which includes electronics, beauty products and restaurant gift cards. In addition to the fun activities, you will be entertained with good music from known artists including Matt and Carla Stinton, Northern Pitch and Troy Hudson. Even though the site has a parking space, it is always encouraged to use public means for conveniences. This is another festival that you will definitely love, especially with your family.

Portland Harvest Festival

Address: Deering Oaks Park, Park Ave, Portland, ME 04101

Website: Portland Harvest Festival

Takes place: September

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3. Early Music Festival [Last event in 2019]

Posted by Portland Conservatory of Music on Sunday, 2 February 2020

If you love music, then without a doubt you will love the Early Music Festival that is held every October. The event is dedicated to bringing together artists from all over the world who specialize in classical music from the late Renaissance to the Baroque periods. The festival has so far hosted many famous artists who never fail to wow the crowd with their amazing talents. Some of the artists that have performed in the concert include the likes of The Berry Collective, which is led by Sylvia Berry, a fortepianist, and Ensalada, a group of three consisting of Lydia Forbes, a violinist, Myles Jordan, a cellist, and Timothy Burris who is in charge of the lute and guitar.

Early Music Festival

Website: Early Music Festival

Takes place: October

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4. Harvest on the Harbor

Posted by Harvest on the Harbor on Wednesday, 23 October 2019

If you are a foodie, you will love Harvest on the Harbor whose main mission is to celebrate the local restaurants in Maine. Hosted in October, Harvest on the Harbor festival ensures that tourists and food enthusiasts get an opportunity to discover the charm of Maine’s culinary scene. This is not just a food festival - beer, wine, and spirits from the locals and all over the world are also celebrated. At the festival, you will also get to enjoy the company of award-winning chefs and live entertainment. This is definitely a fun way to shop, sip, and snack.

Harvest on the Harbor

Website: Harvest on the Harbor

Takes place: Usually held in October

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5. Portland Chamber Music Festival

Posted by Portland Chamber Music Festival on Monday, 7 October 2019

Portland Chamber Music Festival is an annual festival that focuses on bringing together well-known artists from all over the globe to perform their innovative classical music. The event is normally held annually every August for two weeks. Some of the features the event is known for includes education and engagement programs appropriate for all age groups. In addition to enjoying good music and live performances, guests also get the opportunity of socializing with the artists in an informal setting, giving them the chance at sharing musical insights and personal connections.

Portland Chamber Music Festival

Website: Portland Chamber Music Festival

Opening hours: August

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6. Portland Wine Week

Portland Wine Week!! We are offering a special pairing for the rest of the week. Ever tried the grape erbaluce? It’s a...

Posted by Sur Lie on Thursday, 21 June 2018

If you love wine, then come June, you should visit Maine. Visiting Portland during this time of the year will give you the opportunity of attending and enjoying Portland Wine Week. The festival is normally hosted at The Falmouth Country Club and it features wine dinners where guests get to enjoy the creativity of local chefs, classes and seminars where they will learn the art of wine, and tasting events where guests get to try out different types of wines. Free transport is normally provided by Maine Limousine.

Portland Wine Week

Address: One Congressional Drive, Falmouth, ME 04105

Website: Portland Wine Week

Takes place: June

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7. Wizard Fest [Last event in 2019]

Editor's Note: Photo taken from the establishment's official social account

You’ve got to be in it to win it! Best costume at #WizardFest will go home with prizes! Are you ready #HarryPotter...

Posted by Port City Music Hall on Thursday, 26 September 2019

If you intrigued by anything to do with magic and sorcery, you need to attend this festival. Hosted annually at Port City Music Hall, Wizard Fest is a huge opportunity for guests to meet and mingle. During the festival, you will get to enjoy several activities such as trivia, cosplay, food, drinks, games, and wizard-themed music. Guests get to dress in costumes and the best-dressed of the lot gets the chance to join the costume contest whereby the winner wins cash and other prizes. What are you waiting for? Dress up and come have fun.

Wizard Fest

Address: 504 Congress St, Portland, ME 04101, United States

Takes place: October

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8. Portland Schoonerfest and Regatta [Last event in 2019]

June 21-23, sail aboard the 1906 schooner Mary E at Portland Schoonerfest! Regatta race and sunset sails are available;...

Posted by Maine Maritime Museum - Bath, ME on Monday, 17 June 2019

Hosted by Sailing Ships Maine (formerly Tall Ships Maine), Portland SchoonerFest and Regatta is an annual event. The main aim of the event is to provide experiential sailing education for teenagers onboard tall ships. At the festival, you will get to enjoy the views of the historical Schooners, the Wendameen and Bagheera designed by John Alden in 1912 and 1924 and built at East Boothbay. These are among the classic craft and they are known for their speed and comfort. If you are in Maine, you cannot miss the opportunity of experiencing this tradition with the locals.

Portland Schoonerfest & Regatta

Address: Maine Wharf, 68 Commercial Street, Portland, Maine

Website: Portland Schoonerfest and Regatta

Takes place: June

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9. Maine Restaurant Week

Who feels lucky? Enter to win a fun escape to Cliff House and dining at The Tiller Restaurant >> https://www.mainerestaurantweek.com/winmrw. Thank you for being part of the MRW community. Cheers and good luck!

Posted by Maine Restaurant Week on Saturday, 1 February 2020

If you are a foodie, you will definitely want to attend Maine Restaurant Week. During this festival, you will get to enjoy both local and delicious dishes prepared by Maine’s chefs and bartenders. During this festival, customers get to enjoy specially priced menus that feel downright decadent. In addition to enjoying delicious meals, guests also get to enjoy other activities such as food tasting, interacting with experts, and discovering new joints where you can enjoy meals. The event was recognized by LUX Magazine as the Best Restaurant Promotional Event in their Hospitality Awards. Take friends and family along for a delicious, food-filled week at this event.

Maine Restaurant Week

Website: Maine Restaurant Week

Takes place: March 1 - 12

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10. Christmas Boat Parade of Lights

This is the Annual Portland Harbor Boat Parade of Lights in Portland Maine! :) LOVE THIS! MERRY CHRISTMAS PORTLAND HARBOR PARADE OF LIGHTS! :)

Posted by Christmas Wishes and Dreams on Wednesday, 10 June 2015

If you are wondering about what to do during this Christmas with friends and family, your answer could be the Christmas Boat Parade of Lights. Also known as the Portland Harbor Christmas Boat Parade, this event features fireworks displays and a spectacular pilgrimage of lit-up boats which you can view from the waterfront. Keep your eyes peeled for Santa!

Christmas Boat Parade of Lights

Address: 56 Commercial St, Portland, ME 04101, USA

Takes place: December

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Enjoy festivals in Portland, Maine

Portland me waterfront
Source: Photo by user Bd2media used under CC BY-SA 4.0

There is no better way to mingle with locals and understand their culture than attending festivals. In Portland, Maine there are lots of festivals to attend to give you a glimpse into its rich culture. Choose one, plan your trip, and enjoy.

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Any must-sees we missed? Tell us about them in the comments section or write a post here to help out fellow travelers!
Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.

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Irene Mwikali is a graduate student in Kenya who has a passion for travelling and exploring the world. Currently, her love for travel has taken her to several destinations including South Africa,...Read more

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