Kicking off Thursday, Portland is buzzing with live music, sunsets, and summer tradition. Thompson’s Point has the free Summer Sunsets Live concert series, featuring local bands like Sunburned Sharks and Frenzie, alongside an array of food trucks, local beers, and unbeatable views of the Portland waterfront. It is kid and pet-friendly—grab some friends and make an evening of it as the sun dips behind the Fore River, according to Thompson’s Point’s official calendar.
Tonight, music fans can catch Bella’s Bartok with Muddy Ruckus for free at Portland House of Music, doors open at 8 PM. Portland House of Music continues to deliver a packed week, including tributes and themed parties—check out their website for full details. For more waterfront excitement, Old Orchard Beach lights up at 9:45 PM with a classic fireworks display right at Palace Playland. Plan ahead for a sparkling show on the sand, as listed on Old Orchard Beach’s event page.
Friday and continuing all weekend, Guster on the Ocean returns as one of Portland’s signature summer festivals. Friday night brings the sold-out Guster “Hits and Bits” variety show at State Theatre, blending music, storytelling, and comedy. Saturday and Sunday at Thompson’s Point, it’s a full-scale music festival with Guster plus The Mountain Goats, Hanson, Fruit Bats, Joy Oladokun, Maggie Rose, and more. The festival is all-ages, family-friendly, and packed with activities—there’s even a Kids Zone in partnership with the Children’s Museum & Theatre of Maine, open Saturday and Sunday for hands-on art and outdoor fun. Food trucks and specialty drinks will keep everyone fueled for dancing and listening, as reported by On The Ocean Fest and State Theatre.
For shoppers, Thompson’s Point also hosts the Lost and Found Vintage Market, the largest vintage pop-up market in Maine, open through the weekend. The event features dozens of vendors with antiques, vintage clothes, food, and drinks inside the historic Brick South building.
Whether you’re a music lover, foodie, family explorer, or just want to experience the unbeatable summer vibe of Portland, you’ve got something unique every day and night this week. For more block parties, local cruises, and last-minute discoveries, keep your eyes on sites like Portland Old Port and the official Portland events calendar—August is brimming with magic.
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