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.  A big thanks to our sponsors:  • Commonwealth of Massachusetts and Senator Nick Collins • Monarc Development • Massachusetts Convention Center Authority • Dedham Savings • Rockland Trust • Massport • Eastern Bank • Seaport Development at WS Development • Roza Lyons • Stop &amp; Shop • Tufts Medicine • Eversource • UMass Boston • South Boston Dental Group • WinnCompanies • Stanton Insurance • ICON Architecture • Tempco Roofing • Elliott Physical Therapy • HRP Group • Power Home Remodeling • Pierce Atwood • Rep. David Biele • Publico/D&amp;D Hospitality • O'Brien Funeral Home • Sounder Systems • Dunphy Management • Livetech • Ironworkers Local #7 • Mass Bay Credit Union • JCALPRO • JCDecaux • Projection  For more information and the latest updates, visit the official South Boston Street Fest website at  <a href="http://www.southbostonstreetfest.com">www.southbostonstreetfest.com</a>.

South Boston

South Boston Spring Stroll

Celebrate the season at the annual South Boston Spring Stroll The South Boston Chamber of Commerce and South Boston Neighborhood Development Corporation invite you to welcome the season in style at the annual Spring Stroll on Thursday, May 8, starting at 4 p.m. Enjoy a relaxed evening exploring Broadway and beyond while discovering exclusive discounts, special promotions, and delicious food from South Boston’s vibrant small businesses and restaurants. It’s the perfect chance to pick up a thoughtful gift just in time for Mother’s Day! From 5–7 p.m., enjoy the upbeat sounds of The Late Risers as they bring live music to both East and West Broadway, creating a festive atmosphere throughout the neighborhood. Need a lift? Hop on one of our complimentary Pedicabs, available from 6–8 p.m., for a fun and easy ride between your favorite shops and stops. For event updates and more information, visit <a href="southbostonchamber.org/spring-stroll">southbostonchamber.org/spring-stroll</a>. Come out and soak up the sights, sounds, and spirit of spring.

South Boston 

S22: conversations

Wondering what to do in Boston? Places to eat? Free activities? Good for a group? Date night spot? Girls night out? The best things to do? Ask Joyraft!

Best places to go in Boston? Things to do? Places to eat?

Questions & answers about things to do in Boston

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S4: top picks

The most fun, cool and unique things to do in Boston. Can’t miss events, shows and experiences. Concerts, restaurants, bars, free things in Boston and beyond.

The most fun and cool events happening around Boston

Hot and new things to do in Boston

Hot & new

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S11: happening this weekend

What to do in Boston this weekend? From festivals, concerts, performances, free events, screenings and more, Joyraft has the best things to do in Boston.

25+ things to do in Boston/Cambridge/Somerville this weekend

Things to do in Boston this weekend

This wknd

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S21: roundups

Our top picks: outdoor dining, free events, spring festivals, best bars, upcoming concerts, museum parties - the latest in and around Boston.  Slug: joyraft-top-picks-best-things-to-do-boston-ma

Top picks of the best things to do in and around Boston

Joyraft picks: Boston’s best things to do

Roundups ⭐️

Curated by Joyraft ⭐️

S28: calendar experiences

This week in Boston

This week in Boston 📆

This week 📆

S20: c+d experiences

Discover new, unique events and experiences happening in and around Boston. Perfect for date night, good for a group or with a friend. Be the first to know.

The newest events happening in and around Boston

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Just added to Joyraft

S16: editor picks

The most unique and can’t miss things coming up in Boston / Cambridge / Somerville and beyond. Festivals, food, drinks, fairs, concerts, art and free activities.

Unique and Can’t Miss Things to Do in Boston

Can’t-miss things to do in Boston 🚨

Can't-miss things to do 🚨

S2 (A): top experiences

The most popular things to do on Joyraft. Concerts, restaurants, bars, events, parties, openings, kid friendly, date ideas, free things in Boston and beyond.

Top 20 things to do in Boston

Top 20: Joyraft’s most popular

Top 20

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S3 (A): trending experiences

Discover can’t miss events and things to do in Boston. The most fun, unique and cool events coming to the Boston area this spring and summer.

The hottest events happening in Boston

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Trending 📈

S17: interest based

Your guide to everything free in and around Boston. From events, to fairs, to festivals, to outdoors. Joyraft has all the free events happening near you.

100+ free things to do in Boston and beyond

Free things to do in Boston

Free things to do

S19: interest based

Kid-friendly events in Boston

S18: interest based

Where to eat and drink in Boston? Joyraft has Boston’s newest bars, restaurants and specials. Drinks and pre fixe dinner menus. Cambridge & Somerville too.

Boston Bars and Restaurants: Events and Openings

Food & drink experiences in Boston

Food & drink experiences 

Jenni McNeill

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Experiences

South Boston Street Festival

South Boston Spring Stroll