This weekend in Portland, ME

This weekend workshop is designed for female-identifying sea kayakers at the novice to intermediate level who want to feel confident, safe, and self-reliant on the water. Participants build a strong foundation with effective paddling strokes and techniques for power and efficiency, practice rescue skills and safety protocols, and deepen their understanding of ocean conditions and dynamics. The sessions also cover navigation and how to plan trips. The setting is welcoming and upbeat, encouraging participants to take on new challenges with steady support so they can broaden their sea kayaking adventures.

A 45-minute, all-levels yoga class at Toad&Co Portland supports the Dempsey Center’s therapy dog program. It offers a welcoming space to move, breathe, and reconnect with yourself and the community. Expect an inclusive, well-rounded practice with mindful movement, breathwork, and restful moments, and there may be a few special canine guests. This pay-what-you-can session has a suggested donation of $15, and 100 percent of contributions go directly to Dempsey Dogs, whose work brings comfort, connection, and healing to individuals and families facing cancer. After class, stick around to connect with others, enjoy coffee, learn more about the Dempsey Center, and receive 30 percent off in-store. Take care of yourself while helping provide care for others.

Settle in for casual Magic Commander games with fellow players in a friendly, low pressure setting. Open play is free, and you can stay the whole time or just stop by for a bit. Participants who play and sign in using the Magic Companion app will receive a free Magic promo.

Team Envol hosts a free, interactive swimrun clinic at East End Beach designed to help athletes prepare for the ÖTILLÖ Casco Bay Swimrun. Led by Envol coach Marcus Barton, it welcomes all abilities with no membership required. The session covers race strategy, gear, transitions, and efficient techniques for both running and swimming. Participants should arrive in swimrun gear, and bringing a friend and questions is encouraged. Expect practical tips from experienced Team Envol members, a light pre-race workout, and opportunities to meet fellow swimrunners. The clinic lasts about 60 minutes including transition practice and is kept at a super easy pace. An advanced option is available for experienced participants. There is time afterward for packet pickup.

At Thompson’s Point, this event welcomes families by offering free entry for children three and younger. Public ticket sales are announced.

Presented by Outback Presents, Kathleen Madigan brings the Flying Cats & Marching Armadillos Tour to the State Theatre in Portland, Maine. This performance welcomes attendees of all ages.

More shows will be announced soon. Check back for updates as details are released.

A night of dancing takes place every Saturday.

Limitless Wrestling brings the 2026 Vacationland Cup tournament to the Portland Expo, presented by Bull Moose. ECW legend and TNA Hall of Famer RHYNO is confirmed for his Limitless debut. Announced entrants include The Spark Jada Stone, plus either 23 HAZARD or Aiden Aggro. A special meet and greet is available before the event, and tickets are on sale.

Catch comedian Kathleen Madigan live for her Flying Cats & Marching Armadillos Tour at State Theatre in Portland. The show is a stand-up set from one of the most successful road comics, featuring her sharp, carefully crafted joke writing and storytelling.

Legendary New Hampshire rock band Say Zuzu returns to Portland for an all-ages show at Bayside Bowl with special guest Whitney Walker. Say Zuzu emerged in the early 90s alt-country movement that also produced acts like the Old 97s and Wilco, toured extensively across the U.S. and Europe, and later reunited with label head George Fontaine to sign with Strolling Bones Records, resulting in the retrospective Here Again and No Time to Lose, the band’s first new album in nearly twenty years. Whitney Walker, a critically acclaimed alt-psych-freak-folk songwriter on RascalZ RecordZ, has been touring behind a debut album and a recent EP, with a third studio release titled Blood Harmony forthcoming and ongoing collaborations that include baritone saxophonist Dana Colley and producer Dan Capaldi. Tickets are $20 in advance and $25 at the door.

This SwimRun weaves across the Casco Bay Islands, pairing saltwater swims with runs over rugged shoreline. Expect shifting tides, island to island crossings, scrambles over rocks, and views of historic landmarks, all set against the distinctive character of Maine’s East Coast. Open to solo athletes and teams, it is recognized as the birthplace of the first official SwimRun in America and still reflects the spirit of where it all began.

Shalom Sunday is a summer community gathering in the park featuring complimentary bagels and coffee, time to connect with TBE staff members, and playful activities for families. A designated space is set aside for babies and toddlers two and under to enjoy together. Bagels are provided by Rose Foods while supplies last.

Prioritize personal protection with a comprehensive course designed to build legal knowledge and confidence for responsible concealed carry. Participants receive the certificate needed to apply for a Maine Concealed Handgun Permit. Instruction covers handgun basics and shooting fundamentals, strategies for avoiding conflict and improving situational awareness, the psychology of violent encounters, and the legal aspects of using deadly force, including what to do in the aftermath. Home security and home defense are discussed, along with gear and gadgets for effective concealed carry. A live Q&A with USCCA Certified Instructors is included. The course takes place at Cabela's in Scarborough, Maine. Registration is handled by Cabela's.

Walk & Roll is a weekly neighborhood stroll where participants decide the route together, zig and zag through town, and head back to a small park. It centers on friendly company and is open to people of all ability levels.

Join Guster’s Adam Gardner for a screening of the documentary Antimiki about a trip to the Peruvian Amazon, where he and his wife lived with and learned from indigenous community leaders. The film explores life-and-death struggles tied to illegal logging and the connections between music and the people sharing those stories. The screening runs about 30 minutes, followed by a Q&A. Doors open at 2:00 PM.

Experience a weekly rooftop celebration of reggae, dancehall, and sound system culture on the Bayside Bowl rooftop. It begins with a Caribbean cookout, flows into a sound system warm up, then builds into a high energy party as selectors keep the music moving. Expect flavorful food, cold drinks, and a welcoming community vibe. Admission is free early, with a $10 cover later in the evening.

Set sail for an unforgettable wine experience in Portland, Maine. You’ll cruise through Casco Bay’s scenic waters with views of lighthouses, historic forts, islands, and waterways, guided by sommelier Erica Archer. During the voyage, you’ll explore five South African wines, learn about the regions and grape varieties behind them, and build skills for tasting, evaluating, and pairing wines. A box of cheeses, cured meats, and snacks is included, and guests must be 21 or older.

This three day pass for Guster On The Ocean grants access to three performances, beginning at State Theatre and continuing with two shows at Thompson's Point. One purchase covers entry to all three dates.

See Vanna live at Aura in Portland. The show is scheduled for the evening, so come ready for a great night of music.

LeMaire Lee takes the stage at Empire Comedy Club for a stand-up performance. The Austin-based comedian, writer, and creator was born in Detroit and first leaned on humor as a way to protect himself in a family where jokes were part of daily life. That perspective, rooted in finding laughter during tough times, grew as he climbed the Philadelphia scene and earned recognition as an emerging act. He co-hosts the podcast Panties in the Mouth, also known as PITM, with fellow comedians and close friends Andy Malafarina and Nate Marshall, and he is a producer on Matt and Shane’s Secret Podcast.

Rabbi Chaim Litvin, known as the Bourbon Rabbi, leads an evening that pairs a guided tasting with rich storytelling. As the founder of the Bourbon Rabbi brand, he has shared this experience in communities across the United States and abroad, bringing industry knowledge and a passion for uncovering the Jewish narrative within America’s signature whiskey. Through a selection of premium bourbons, he explores how the spirit evolved, the meaningful role Jewish contributors played in shaping the industry, and the connection between bourbon, kosher practice, and Jewish tradition. The program blends history, humor, and Torah insights into an engaging experience for dedicated bourbon fans as well as anyone interested in a distinctive night out.

Deep Blue C Studio Orchestra performs at Vinegar Hill Music Theatre in Arundel, Maine. This event features the ensemble in a live concert at the venue.