Things To Do in Boston This Weekend: September 5-September 7

Boston has a packed schedule this weekend with live entertainment, art, and fashion. Major highlights include Fashion in the Park in Roslindale, the 2025 Boston Arts Festival on the waterfront, and the Institute of Contemporary Art's Play Date in celebration of International Dot Day. In addition to the family events featuring artistic activities, the city offers a wide range of music and comedy, making this a great weekend for everyone.

The 3rd Annual Fashion In The Park, presented by Save Our Streets-Boston, makes its triumphant return as a free family-fun celebration of style, creativity, and community in Roslindale. Fashion In The Park includes a live runway show with local designers and models and performances by talented artists from the area. Attendees will see art installations, music, vendors, and much more as part of the programming. The event creates a celebratory vibe, showcases local talent, and fosters connection and pride within the surrounding community.

The annual Boston Arts Festival returns to highlight the city's vibrant creative community with a weekend of fine arts and live music. Since its founding in 2003, the festival has stood as Boston's only event dedicated exclusively to showcasing local talent. Free and family-friendly, it brings together artists and musicians from across the area in a historic waterfront park. Rain or shine, the festival offers a unique opportunity to celebrate Boston's cultural richness.

The ICA's September Play Date on Sept. 7 celebrates International Dot Day, a global tribute to creativity, courage, and collaboration inspired by Peter Reynolds' "The Dot." Families can enjoy hands-on artmaking in the Bank of America Art Lab and State Street Corporation Lobby, animated short films of Reynolds' stories, and picture book readings in the galleries. Highlights include meeting Reynolds himself for a book signing and Q&A. With art, film, and interactive activities, the day offers an inspiring celebration of imagination and community, perfect for sparking creativity across all ages.

The arts and entertainment scene in Boston is buzzing this weekend with music, comedy, and cultural events. Entertainment highlights venues around the city. From headline artists to local community events, the variety is vast.