What to Expect at the 26th Annual South Boston Street Festival

Get ready, Southie! The South Boston Street Festival is Saturday, September 19th from 11am–4pm (rain date: September 26th)! East Broadway between I and L Streets will transform into a giant neighborhood block party complete with shopping, entertainment, food and more. Caught in Southie will be there with plenty of CIS merch, including key chains, stickers, temporary tattoos, plus limited-edition South Boston baseball caps and Caught in Southie shopping totes with patches!
Here’s What You Can Expect
Shopping + Art
Over 100 local shops, artists, and community groups will line Broadway with can’t-miss deals, unique finds, and creative works. It’s the perfect excuse to shop small and show some love to the neighborhood’s businesses. Pam from Habit will be celebrating her 20th Street Festival, so stop by and say hello. Plus, Style Exchange will host a pop-up thrift in the South Boston Library municipal lot!
Food + Drink
Live Music + Entertainment All Day Long
Two stage will feature nonstop entertainment. From local favorites like Thomas Park and Shanel Sugar, to up-and-comers from Michael Caputo’s MusicBall Entertainment. Also catch performances from Woods School of Irish Dance, Miss Linda’s School of Dance, and country line dancing from 603 Line Dancing . Don’t miss self-defense demos from Ultimate Self-Defense too!
Family Fun
Kids will have a blast with touch-a-truck, face painting, balloon twisters, caricatures, pirates, princesse, the Bubble Fairy, and even K-Pop Demon Hunters! Expect lots of smiles and plenty of photo ops.
Community Connections ❤️
Celebrate the community. Local nonprofits, neighborhood groups, and community organizations will be out in full force, sharing resources, raising awareness, and connecting with residents. From longtime neighborhood advocates to grassroots initiatives making a difference every day, the festival is a perfect chance to learn more, get involved, and show your support for the organizations that help South Boston thrive.
✨ Bonus: This year, the Thomas J. Butler South Boston Small Business Leadership Award will be presented to Nikki McCart and Lisa Walsh of MW Hair Studio at 11:30 am on the Karen Stanley Stage.
Also – Parking and Traffic Alert:
The annual South Boston Street Festival will take place on Saturday, September 19 on East Broadway, between I Street and L Street. Temporary parking restrictions will be in place on the following streets on Saturday:
- East Broadway – Both sides, from I Street to L Street
- Municipal Parking Lot (off East Broadway, by the Boston Public Library) – All spaces within the parking lot
- L Street – West side (odd side), from L Street heading southerly for the first two streetlights
- K Street – Both sides, from East Third Street to Emerson Street
More information is available here!
Full List of Vendors Popping Up on Saturday:
BOTTEGA DEL SUD
Capo Restaurant & Supper Club
Common Craft
Deja Brew
Fat Baby Sushi & Cocktails
Hunters Kitchen And Bar
Layla’s American Tavern
Lincoln Tavern
Loco Taqueria & Oyster Bar
Mei Mei Dumplings
Park City
PKL X Pig Beach BBQ
Playa Bowls
Publico Street Bistro
Roza Lyons
Sal’s Ristorante and Pizzeria
The Broadway
The Playwright
Lucky’s LoungeSMALL BUSINESS
4103designs
Barre Groove
Bento Real Estate
Bohdii Boutique
Bringing Up Baby
Broadway Golf Club
Caught in Southie
Clover Clubhouse
Club Golden
Club Pilates South Boston
Format
Frios Gourmet Pops
habit
Hamersley’s Pantry
Harry & Lou
House of Ivy
LUXE home interiors
Maker / Scholar
Mary Kay Skincare & Cosmetics
Michaela’s Market
Mystryde Athletic Club
Native Sun
Northern Attitude Apparel
Peter Welch’s Gym
PickleBOS
SEAPORT MEDSPA
Show Dog’s Closet
South Boston Dental Group
South Boston Moms Club
South Boston Party Banners
Stapleton Florist
Style Exchange Boston
Summer Street Wellness
The Dirty Italian
The Moment
The Point Clothing Lounge
Wolfie’s All Natural Treats
You Vs You TrainingNONPROFIT / COMMUNITY / ARTISTS
Adopt a Platoon
Southie Style
Boston Fire Department
South Boston Youth Lacrosse
Boys & Girls Club South Boston
Castle Island Association
Catholic Charities Labouré Center
D Putnam Art
EastieRides
Fitzgerald Post
Fourth Presbyterian Church
Friends of the South Boston Branch Library
Julie’s Family Learning Program
Kick Off for Kids
Linda Conley Art
Norman Crump Studio
South Boston Catholic Academy
South Boston Community Health Center
South Boston Neighborhood House
St. Peter Academy
Watercolors by Dan McCole
We Support South Boston Initiative
Wildlife and Watercolors

Maureen Dahill is the founder of Caught in Media. Once a longtime wardrobe and prop stylist for brands such as Rue La La, TJ Max & Hasbro, she is a devoted lover of vintage clothing, Martini Mondays, Castle Island, AND a 4th generation South Boston native. Mother of three, married to Peter G.

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