Upcoming Festivals

The Meet Boston Parade of Sail will highlight the day’s activities as vessels parade in flotillas from Broad Sound into the main channel of Boston Harbor turning at Charlestown, before proceeding to their assigned berthing areas. Public viewing of the parade will be spectacular from Castle Island, the Seaport District, the Boston Waterfront, East Boston, the North End, and Charlestown.

If you're into comics, sci-fi, horror, anime, gaming, or cosplay, come share our playground. You'll feel out of this world – and right at home.

The annual Boston Puerto Rican Festival will be held on July 25 & 26, 2026, with the Puerto Rican Parade occurring on Sunday, July 26, 2026. Join us for a lively celebration, drawing over 20,000 attendees, featuring food and merchandise vendors, carnival rides, exciting entertainment, and more!

A free, family-friendly jazz celebration at the Hatch Memorial Shell featuring Grammy-winning headliners Ghost-Note, rising star Tyreek McDole, and Boston’s own BT ALC Big Band. Expect food trucks, artisan vendors, and a vibrant community atmosphere.

Held at Pinebank Field by Jamaica Pond, this free community festival highlights local bands and food trucks. A neighborhood favorite with diverse performances.

A full-day cultural celebration at Boston Common with live African music, drumming, dance, fashion shows, authentic cuisine, and a bustling marketplace. Free admission, highlighting unity and heritage.

Jamaica Plain’s porches transform into stages for local bands, theater, and dance. This grassroots festival runs noon–6 PM, with a special “Community Hour” at 3 PM. Free and open to all.

The 15th annual Boston Jazz Fest at South Boston Maritime Park features international jazz artists, including Groovallottos and Charu Suri. Friday evening and all-day Saturday performances celebrate jazz in all its forms.

Pop-punk nostalgia comes alive at Leader Bank Pavilion with Boys Like Girls, Cartel, Hit The Lights, and Cute Is What We Aim For. A one-night-only event celebrating the music of the 2000s.

New England’s largest gospel music celebration returns for its 26th year at Leader Bank Pavilion. Free admission, featuring national and local gospel talent plus an interfaith prayer service.

The Caribbean Rum & Food Festival brings a full day of island culture to Boston with premium Caribbean rums, handcrafted cocktails, authentic dishes, artisan vendors, and live entertainment. Hosted outdoors at Roxbury Community College, this 21+ festival showcases Caribbean destinations, music, arts, and flavors while supporting programs for children with disabilities. With eight hours of food, drinks, and cultural experiences, it’s a standout late‑summer event for young professionals looking for vibrant energy, great music, and a taste of the islands close to home.

A waterfront showcase at Christopher Columbus Park featuring Boston-area visual artists, musicians, and performers. Free admission, family-friendly, and a staple since 2003.

A neighborhood-wide celebration with porches and local venues hosting live performances. Expect eclectic acts across Roslindale Square.

A free outdoor event at Herter Park Amphitheatre showcasing diverse vocal ensembles from across New England. Genres range from barbershop to modern pop.