Must Do Fairs + Festivals

Must Do Fairs + Festivals

upcoming annual events

Across Greater Portland we are bringing the fun with fairs, festivals, and exciting events all year long and for all ages, Enjoy rock, country, blues, big band, and folk music everywhere you go and plenty of events to keep you smiling!

Due to COVID-19, this page will be updated to address canceled events and new developments.


Bach Virtuosi: Event rescheduled for August 16-23, 2020 more info
Portland Chamber Music Festival: 27th Summer Festival Online from August 2-13, 2020 more info
Maine Outdoor Film Festival: Re-developed and scheduled for July 30 – August 2 more info

Bug Light Kite Festival, Photo Credit: Marissa Davis (@rissalovely on Instagram)

Bug Light Kite Festival

Annually in May

CANCELED 2020

On the third weekend of May the sky above Bug Light Park is lit-up with kites of all shapes and colors. Bring your own or buy a kite while there and take advantage of their BBQ lunch fundraiser. Hosted by South Portland Historical Society and Nor’Easters Kite Club and Kites Over New England. Learn More

Sailing Ship Maine Docked, Photo Credit: Sam Fiorillo

sailing ships portland

Annually in June

CANCELED 2020

Portland’s Schoonerfest and Regatta is an annual event kicking off the sailing season. It features upwards of seven large schooners racing and parading under sail together in Portland Harbor with passengers participating on-board and from the shore. Learn More.

Maine Brew Bus Cellardoor Winery Tour

Portland Wine Week

Annually in June

CANCELED 2020

Portland’s week long wine festival and celebration includes pairing and performance events, incredible wine dinners, tastings, educational classes and seminars, special menus, a passport tour of dozens of local restaurants and their wine lists. Learn More.

Yarmouth Clam Festival, Photo Credit: wikimedia commons NewTestLeper79

Yarmouth Clam Festival

Annually in July

CANCELED 2020

Always the third Friday in July, the Yarmouth Clam Festival attracts visitors from all over Maine and beyond, as well as locals who line up their beach chairs on the side of the main drag a few days before the parade for the best possible seat. Learn More.

Cumberland Fair Daytime, Photo Credit: Chris Riccardo

Cumberland Fair

CANCELED 2020

Get in touch with Maine’s agricultural roots at the Cumberland Fair. The epitome of tradition, this historic event started in the 1800s and today it has everything you would expect from a local fair: carnival rides, a petting zoo, and of course lots of indulgent fair foods. Learn More.

Tents at Freeport Fall Festival, Image provided by Visit Freeport

Freeport Fall Festival

CANCELED 2020
Next year this event will be held October 1 – 3, 2021

The Freeport Fall Festival attracts thousands of people to Freeport for a day of art, music, and fun. Over 100 artists exhibit works ranging from photography, oil, watercolor, mixed media, fine craft, and jewelry set to the tunes of live musical performances throughout the day.  Learn More.

Photo Credit: Will Wenzel

Harvest on the Harbor

Annually in October

Re-developing Event for 2020

Harvest on the Harbor™ is Portland, Maine’s annual food & spirits festival featuring a delicious, diverse and engaging line up of events. The event curates experiences and partnerships that hope to appeal to foodies of all kinds, offering a taste (and sip) for every appetite.  Learn More.

2018 Parade of Lights, Photo Courtesy of Visit Freeport

sparkle Celebration in freeport, maine

Annually in December

Visitors seeking a town-wide holiday celebration in a Maine seaside village will find it here. Each year, Freeport presents one of Maine’s most popular holiday celebrations with everything from a Parade of Lights down Main Street to their famous Talking Christmas Tree.    Learn More.

upcoming events

your #1 resource for everything happening in Greater Portland

The Greater Portland region hosts a number of festivals and events throughout the year. Find seasonal and annual fairs and festivals in Maine celebrating music, food, beer, history, dance, ethnic heritage, communities and more.

Have an event and want to post to our website? Learn More