Portland, Maine Buzzing With Summer Fun

For anyone in Portland, Maine this week, it is a stellar time to get out and explore because the city is overflowing with great summer events. This evening, wrap up your Thursday at the Eastern Promenade’s Fort Allen Park Gazebo for the Summer Concert at the Gazebo, running from 6 to 7 PM. Bring a blanket, kick back as the sun sinks over Casco Bay, and take in some live local tunes according to the City of Portland's official events schedule.

If you are looking ahead to the weekend, listen up: The Cruising Casco Bay Concert Series continues Friday night with a special show on the water hosted by Casco Bay Lines and 98.9 WCLZ. Toby McAllister & The Sierra Sounds return for this sunset cruise. The concert—always a quick sellout—offers ocean breezes, great music, and a cash bar. All the details can be found on Portland Old Port’s guide for the weekend.

Not into cruising? You can catch the Hearts of Pine, Maine’s own professional soccer squad, with a watch party at Rising Tide Brewery. Grab a pint, cheer on the local club, and enjoy food from The Galley. According to Portland Old Port, it is first come, first served, so drop by early if you want the best seat.

Thursday night, Bayside Bowl becomes a must for music lovers as UK funk legends The New Mastersounds hit town on their “Ta-Ta For Now” Farewell USA Tour. This show promises soul, deep rhythm, and unforgettable energy, with openers The Kevin Roper Project. This may be your last chance to catch the veteran quartet live in Maine.

Amigo’s Summer Madness also keeps rolling with outdoor music, including an offbeat blues set from Fat Knuckle Freddy—a duo known for their rowdy, one-of-a-kind sound.

Looking for fun during the day? Portland Paddle hosts free early morning paddles for sea kayakers and stand-up paddlers twice a week during the summer. Just show up with your own gear, or rent a vessel if you need one. These hour-long sessions let you start your day on the calm waters of Casco Bay in the expert company of local staff.

For the foodies among you, there are unique tours and tastings all weekend long, including behind-the-scenes looks at barrel rooms and oyster shucking lessons with local farmers. Payson Park comes alive with local art and music, perfect for families and anyone wanting to explore the creative energy of the city.

Drag Brunch returns on Sunday—an all-inclusive, joy-filled way to wrap up your weekend in the city. And don’t forget, the Maine Lobster Festival starts this week in nearby Rockland, according to Untamed Mainer, and it is a bucket-list event for seafood lovers.

With concerts, cruises, food, trivia, outdoor paddling, family art days, and laughter filling every corner, there has never been a more fun or diverse week to be in Portland, Maine.

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