Celebrate 25 Years of the South Boston Street Festival on September 20th

Get ready, Southie! The South Boston Street Fest is celebrating its 25th year, and the party is going to be epic! On Saturday, Sept. 20, 2025, East Broadway between I and L streets will be transformed into a vibrant, music-filled, food-packed, shopping-centric block party from 11 a.m. to 4 p.m. (Rain date: Saturday, Sept. 27.). You can get all the details here! 

Negroni Week at Nautilus Pier 4

Join Nautilus for a hands-on Negroni class on September 27th! You’ll learn the history plus make the classic cocktail. You can get your tickets here! Plus, all September long, Nautilus Pier 4 will feature a Negroni-inspired charity cocktail, “From the Barrel #8”! $2 from each cocktail sold will go to Slow Food. 

Harvest Day at Pappas Way

Celebrate the season with food, friends, and a little fall magic on Thursday, September 18 from 5 – 8pm. Visitors can expect seasonal classics and neighborhood cheer, from cuddling up with baby animals from McDonny’s Farm (they’re udderly adorable) to testing their skills at tabletop games, or enjoying tasty treats including popcorn, cotton candy, and churros. The Sausage Guy will be grilling up hot dogs, sausages, and burgers, and Decanted Wine will be pouring beer, wine, and mocktails for the grown-ups.  You can learn more here! 

Free CPR/Stop-the-Bleed class at Moakley Park 

Learn lifesaving techniques at a special and free class at Moakley Park on Monday, September 22nd at 6pm offered by the South Boston Collaborative Center in partnership with Boston Harbor Now, South Boston En Accion, and the Boston CERT Team. Five instructors will teach participants how to perform CPR on adults and infants, as well as how to control major bleeding using tourniquets and wound packing materials. Food will also be provided.  Anyone interested can sign up using this Google Form:  Google Form Sign Up: CPR / Stop-the-Bleed.

Red Bull Cliff Diving World Series Returns this Weekend!

The highly-anticipated 2025 Red Bull Cliff Diving World Series  will make its triumphant return to Boston Harbor on September 19 and 20, 2025 and will be the only stop in the United States and the final stop of the series. It is once again open to the public, free of charge.

Have a great week!