South Boston Street Festival

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.) Since its debut in 2000, the South Boston Street Fest has grown from a sidewalk sale into one of the neighborhood’s most beloved traditions, drawing thousands each year. Now in its silver anniversary year, the South Boston Chamber of Commerce and South Boston Neighborhood Development Corporation are pulling out all the stops — with more than 100 local shops, restaurants, artists, and community groups coming together to showcase the very best of Southie. Two stages will keep the entertainment going all day long, featuring something for everyone, including: Shanel Sugar and Friends, Seldom Chalant, Tom Baker &amp; the Troublemakers, Fionn Lonergan, and up-and-coming acts from Michael Caputo’s MusicBall Entertainment. The celebration begins with The Late Risers strolling the streets to get the crowd excited. This year’s Thomas J. Butler South Boston Small Business Leadership Award will go to Joey Arcari, owner of Monarc Development. His presentation will take place at 11:30 a.m. on the Library Stage, which will now be known as the Karen Stanley Stage. The ceremony will be followed by performances from Woods School of Irish Dance and Miss Linda’s School of Dance; singers and dancers from the St. George Albanian Orthodox Cathedral; and self-defense demos from Ultimate Self-Defense. For the kids, there’s no shortage of fun — touch a truck, balloon twisters, caricature artists, face painters, pirates, princesses, and yes … Bluey will be there! Foodies, come hungry. Enjoy street-side dining from The Broadway, The Playwright, Roza Lyons, and Deja Brew, plus grab-and-go bites from neighborhood favorites Publico Street Bistro, Sal’s Ristorante &amp; Pizzeria, Capo Restaurant &amp; Supper Club, Lincoln Tavern &amp; Restaurant, Layla’s American Tavern, Fresh Boston, Playa Bowls, Pig Beach BBQ, Hunter’s Kitchen &amp; Bar, Loco Taqueria &amp; Oyster Bar, Fat Baby, Dig Inn, Bottega del Sud, Park City Southie, and Frios Gourmet Pops. Festival-goers can also score one-day-only shopping deals from local shops, browse incredible artwork from South Boston’s creative community, and connect with local nonprofits making a difference in the neighborhood. The 25th South Boston Street Fest promises a day packed with music, flavor, community spirit — and the perfect chance to celebrate Southie in style.

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South Boston Street Festival

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