JUNE 9
Old Port Festival | Old Port
Make it a point to be in Portland for the 46th annual—and final—Old Port Festival. This longtime community staple is family-friendly, filled with live music, art, and entertainment, and celebrates the heart of Maine’s biggest city.

JUNE 21–24
Schoonerfest + Regatta | Portland Harbor
Sail into summer with famous schooner parades and races between hometown ship favorites. Tall Ships Maine, a chapter of Tall Ships America, co-hosts the festival. A welcome ceremony kicks off the event, which is held during the summer solstice weekend every year.

JUNE 22
Shipyard Old Port Half Marathon + 5K | Fore Street
Run along Casco Bay in a race like no other that features scenic views and historic sites. Participants receive a commemorative shirt for running, and at the finish line, a medal for completing the race. At the end of it all, celebrate at a block party with live music, Shipyard beer, and free food.

JUNE 27–28
2019 Greek Festival | Holy Trinity Greek Orthodox Church
Immerse yourself in Greek culture with live music, traditional dance, and a smorgasbord of Greek fare; eat your way through the weekend at this annual three-day celebration, all provided and prepared by members of the Holy Trinity parish.

JULY 16–18
PBA League: Elias Cup | Bayside Bowl
Don’t miss the chance to see 40 of the world’s best bowlers as they compete in teams to win the Elias Cup. Kick off the competition with a rooftop tailgate on opening night, and over the course of three days, watch as the quarterfinals, semifinals, and finals unfold. Tickets are available online.

JULY 20
Peaks to Portland Swim to Benefit Kids 2019 | East End Beach
Dive into Casco Bay to raise money for kids. Peaks to Portland, a fundraiser for Southern Maine’s YMCA youth development programs, invites anyone 16 and older to swim for a cause. All fitness and experience levels are welcome to try the 2.4-mile race, but being able to swim at least one mile in 40 minutes is advised.

JULY 27
17th Annual Greater Portland Festival of Nations | Deering Oaks Park
Celebrate Maine’s ethnic diversity and honor tradition at this annual one-day event. The free and family-oriented festival offers non-stop music, dance performances, and food from more than 22 nations. The 2019 festival theme is, “From many different nations, to one Maine.”

JULY 27
Summer Session 2019: Maine Brewers’ Guild Beer Festival | Fort Preble
Sample the best beers in the state at Maine’s biggest brewfest. Ticketholders enjoy unlimited beer samples and souvenir glasses, with live music and food trucks. All festival profits go toward supporting the Maine Brewers’ Guild.

AUGUST 24
Portland Fine Craft Show | Congress Street
Explore one of the only crafts shows in Maine to welcome out-of-state and international artists. More than 100 juried exhibitors will have their work on display in a variety of media including baskets, ceramics, furniture, leather, metal, glass, jewelry, and more.