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
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 ships MAINE
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.
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
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
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.
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.
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.
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.
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