Portland Buzzing with Late Summer Fun: Crafts, Music, and Cuisine Galore

Portland, Maine is buzzing with late summer energy and one glance at what’s happening this week shows you exactly why people love this city by the sea. On Saturday, the city center transforms into an open-air gallery for the annual Portland Fine Craft Show. Head down to the Free Street Parking Lot at 120 Free Street between 10 AM and 5 PM, where more than 100 craft vendors will be showing off their handmade creations. Expect everything from jewelry, pottery, and textiles to carved wood and blown glass. Plus, you can catch artist demonstrations and connect with local arts organizations, all for free—this show is known for its friendly atmosphere and high quality, so chat with makers and pick up a truly local souvenir. Shop Maine Craft organizes the event and their reputation among Maine artists is sky high.

If you want to end your evening with music and local flavors, Thompson’s Point is the spot. Saturday night brings the State Theatre Concert Series with the indie band 12 OC scheduled to play from 6 PM to 11 PM. The same venue’s Summer Sunsets Live series continues, so while you’re listening, stroll the waterfront, try something new from a local food truck, and watch the sun set behind the Fore River. According to the Thompson’s Point calendar, this is one of the city’s favorite summer traditions. These events are free, open to all ages, and pet-friendly, making them a natural place for the community to gather.

The Portland Chamber Summer Festival continues this week with a performance at USM’s Hannaford Hall on Saturday as well. Classical and contemporary chamber music fills the city thanks to guest artists from around the world, making this a cultural highlight for musicians and music lovers alike, according to the Portland Old Port.

Food fans should check out the classic Maine Food and History Tours, which are running daily. You’ll taste your way through the Old Port, learn local lore, and maybe discover your next favorite bite. For those who love a challenge, trivia nights are happening citywide—head to a waterfront pub or local brewery, grab a team, and test your Maine knowledge.

Sunday is drag brunch day, a beloved Portland tradition for great food, big laughs, and incredible performances that always sell out, as highlighted by Visit Portland. This is the last weekend of summer before fall starts sneaking in, so treat yourself: stroll the waterfront, dance under the stars, or simply relax in one of Portland’s many green spaces.

Thanks for tuning in, and don’t forget to subscribe for your weekly guide to Portland fun. This has been a Quiet Please production, for more check out quiet please dot ai.