This weekend in Martha's Vineyard, MA

Take to the water for an introductory stand up paddleboard fitness session. The experience lasts about an hour, beginning with gentle stretching and then paddling on your board. The routine varies from session to session while staying accessible for all skill levels. Launch point is Little Bridge. All equipment is included, with paddle boards, paddles, personal flotation devices, and a guide provided.

A longstanding Vineyard tradition returns with the Chilmark Flea Market, now in its 59th year and organized by the Chilmark Church. Browse a field of vendors, from longtime favorites to new faces, offering vintage and antique discoveries, handmade clothing, and other unique finds. Because cell service can be unreliable, many sellers prefer cash or checks, and paying with cash is often the easiest option.

This five week beginner class introduces the fundamentals of Brazilian Portuguese along with insights into Brazilian culture, led by instructor Maria Angela Moreira. Participants build everyday conversation skills, including how to greet others, get acquainted, and share information about themselves. The class is intended for those just starting out. A past participant praised the kindness and patience of the instructors and found it well suited for complete beginners. Tuition is offered at an early bird price of $189, with regular enrollment at $209.

Paddle across Sengekontacket Pond on a guided family-friendly kayaking adventure. You will learn about pond habitats and the local species that rely on them, with stories from a naturalist focused on wildlife and conservation. This registration is for a single kayak and is limited to one participant, with kayaking designed for an active time out on the water. Everyone under 18 must be accompanied by an adult, and details on what to wear and bring are shared at registration.

Join the Children’s Forum at CDF Joy on the Vineyard for a solutions-focused conversation about the well-being of Black children. The forum features Brittany Packnett Cunningham and Dr. John H. Jackson, bringing attention to the challenges Black children are facing while highlighting solutions already working in communities and encouraging leaders, advocates, and families to take action. The event is an in-person program held at Strand Theatre.

At The Maker, brunch centers on unhurried moments and carefully prepared plates. The menu blends cozy staples with bright, seasonal selections, creating a meal that feels like a small celebration. It suits catch-ups with friends, family get-togethers, or a well-earned solo outing. Settle in, enjoy a drink, and take your time over flavors made with care.

Enjoy a full day of favorite bites from 20+ food trucks, along with craft beverages like craft beers, wine, and other drinks at the Cape Cod Food Truck & Craft Beverage Festival. There will also be live music, lawn games, and an artisan market featuring Cape-made goods. This is an all-ages, family-friendly event, and leashed, well-behaved dogs are welcome. Rain or shine, the festival keeps going.

Each summer, Martha’s Vineyard Community Services welcomes friends, neighbors, and supporters for a memorable afternoon centered on generosity, humor, and community spirit. The tradition continues at the historic Allen Farm on Martha’s Vineyard, with Seth Meyers returning as host in a picturesque setting. The celebration raises vital funds for the Island’s umbrella social service agency, sustaining mental health care, early childhood programs, disability services, veterans outreach, services for survivors of domestic and sexual violence, substance use disorder and recovery support, and programs for youth and families. Giving through attendance, sponsorship, donations, or the auction helps strengthen the Island’s safety net so care is available when it is needed most. It is an invitation to dream big and make a meaningful impact.

Enjoy an evening work-in-progress sharing with New York Theatre Workshop at Vineyard Arts Project. The Summer Salon includes light bites, drinks, and a chance to hear theatrical works as they develop. There will also be a project development sharing and artist panel, followed by a post-sharing reception.

Settle in for a live stand-up set from Jackie Flynn. Flynn plays Tony in the Netflix series Loudermilk alongside Ron Livingston, Will Sasso, and Anja Savcic. After making his name in Boston, he was spotted by the Farrelly brothers, which led to roles in films such as Kingpin, There’s Something About Mary, Me, Myself & Irene, Shallow Hal, and Stuck on You. Additional screen work includes The Three Stooges, Here Comes the Boom opposite Kevin James, Special Unit, The Greatest Beer Run Ever, and Ricky Stanicky. Television credits include appearances on The King of Queens, Veep, and Disney Channel’s Bizaardvark, and he continues as a series regular on Loudermilk. His stand-up achievements include winning the San Francisco Comedy Competition, performing at the Montreal Just For Laughs gala, and being selected for the U.S. Comedy Arts Festival in Aspen.

Marino Live Creative LLC hosts an event in Vineyard Haven, Massachusetts. Organized by the company, this gathering takes place in the local community.

Elvis Costello takes the stage at Old Whaling Church in Martha’s Vineyard for a special benefit concert. With a career spanning decades and a signature blend of rock, new wave, and singer songwriter storytelling, the performance unfolds in an intimate setting at one of the Vineyard’s most beloved venues. The evening begins with an opening performance by Will Dailey.

Three Dog Night returns, celebrating a career that spans six decades. This long-running band is associated with remarkable statistics in popular music, and the years 1969 through 1974 are a notable part of its history.

The Oak Bluffs Open Market returns with a lively marketplace set in the park by Oak Bluffs Harbor, showcasing vintage finds, handmade goods, and unique one-of-a-kind items. It offers a friendly path for new and growing businesses, with affordable vendor fees that make it easier to share products and take first steps toward a new venture. Food vendors should have the appropriate Board of Health certifications. A coffee vendor spot remains available for a business eager to reach market visitors.

Join the Envy MV Day Party in Oak Bluffs for a summer hangout with DJs bringing the #ENVYMV vibes to Martha’s Vineyard. The party runs from mid-afternoon into the evening, and early ticket holders get complimentary drink tickets during the first hour while supplies last. Advance entry is for the party only, and there’s also an optional Stress Free VIP add-on with organized transportation details provided by the event organizers.