Portland, Maine Buzzing with Summer Events: From Concerts to Vintage Markets and More

The city is buzzing with summer energy and if you’re in Portland, Maine this weekend, there’s no shortage of unique, exciting events waiting for you. Kicking off the weekend, Casco Bay Lines teams up with 98 point 9 WCLZ for the Cruising Casco Bay Concert Series, featuring Toby McAllister and The Sierra Sounds. This live music cruise at sunset will have you soaking up amazing views, enjoying great tunes, and sipping from a cash bar—according to Portland Old Port, these shows are popular, so hop onboard if you can.

If you’re craving something family-friendly, check out the 150th anniversary of Portland Breakwater Lighthouse, affectionately known as Bug Light. According to the City of South Portland, the festivities run Saturday from eleven to three at Bug Light Park, complete with speakers, crafts, games, actors dressed as lighthouse keepers, food trucks, and more. It’s a free all-ages celebration of one of Maine’s most iconic lighthouses.

For art and vintage lovers, Thompson’s Point is the place to be. Lost and Found Vintage Market is popping up inside Brick South with loads of vintage vendors, food, drinks, and photo ops. The venue’s website highlights plenty of food trucks, a laid-back vibe, and even pet-friendly fun. While you’re there, swing by Summer Sunsets Live—this ongoing series features top-notch musicians, local brews, and unbeatable sunset views over the water, all completely free to attend.

Soccer fans will want to hit Rising Tide Brewing for a Hearts of Pine pro soccer watch party—Portland Old Port describes it as the ultimate way to catch every goal with fellow fans, great drinks, and bites from The Galley food truck. Settle in early for the best seats and bring the whole family for this friendly local experience.

Craving live music? Bayside Bowl is hosting The New Mastersounds as part of their farewell U.S. tour, sharing the stage with The Kevin Roper Project. Portland Old Port calls it a must-see for funk and soul fans. Meanwhile, Amigo’s Summer Madness continues on the patio with Fat Knuckle Freddy headlining Trash Blues 25 number three, promising gritty riffs and raw, unforgettable summer vibes.

On Sunday, wrap up your weekend with Drag Brunch in downtown Portland, or enjoy a guided tasting and origin tour at one of the city’s celebrated barrel rooms as listed on Visit Portland. Explore Back Cove for two days of live music and art, dive into Maine-inspired trivia on the waterfront, or discover the Kotzschmar Organ with a behind-the-scenes look and live demo.

For those wanting to embrace Portland’s quirky side, July twenty-sixth brings the much-anticipated World Naked Bike Ride through the city. Details on the route are kept hush-hush until the last moment—Travel Portland reminds you to check their site and, seriously, don’t forget your helmet.

That’s just a slice of what’s happening in Portland, Maine now and this weekend. Whether you’re up for concerts, food trucks, vintage markets, lighthouses, soccer, art, or just want to watch the sky turn pink over the water, Portland has you covered.

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