History in Motion – USS Constitution Underway on Friday

USS Constitution is scheduled to get underway on Friday, September 19th, from Charlestown Navy Yard at 10:00 A.M. The cruise will be visible from the Boston Harborwalk, Castle Island, and Charlestown Navy Yard. A 21-gun salute will be fired at approximately 11:30 A.M., viewable from Fort Independence on Castle Island. This sail will commemorate Purple Heart Recipients. While you’re out there, you might as well pick up some lunch at Sully’s, right?

Celebrate 25 Years of the South Boston Street Festival on Saturday

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! 

Raise the Bar at Love Child

Elevate your at home bar experience at Love Child on Friday, September 19th from 6 to 7:30pm. You can make your own drink charms, embroidered cocktail napkins, and take home a petite bouquet. It is the perfect way to spend your Friday night. Get tickets here!

Strength Personal Training Class at Medal of Honor Park

On Saturday at 7am at Medal of Honor Park, Michelle Hines from Strength is teaching a workout! Just show up with your mat!   Class is $20.

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.

Luxe Leisure Fitness Studio Open House

Get yourself a Breakfast Sandwich via Lulu Green

Let’s hear it for Lulu Green! Southie’s favorite plant-based fast-casual restaurant on West Broadway was listed in the Eater Boston Best Breakfast Sandwiches in Boston list! Here’s what Eater said below:

This beloved vegan restaurant in Southie piles on the flavors for its plant-based plates. For a Mediterranean-ish morning meal, check out the Brunch Sandwich 2.0, which puts a chickpea egg patty, tofu bacon, potato pancake, and cheddar on a grilled pretzel bun. The goodies are then topped with marinated kale, avocado, hot sauce, and tahini to temper the kick. Wash it down with the spot’s mint cold brew latte.

Try one this weekend!  You can check out the full list here! 

Polish Harvest Festival

Our Lady of Czestochowa parish is hosting a special Harvest Festival on Sunday, September 21st from 10am-6pm featuring traditional Polish food, pony rides, pastries, music and dancing, kids activities and more!

Art Show at Gray’s Hall Opening Celebration

In the Mix Art Show featuring the artwork of  @patchwork.mix opening celebration will take place on Sunday, September 21st from 4pm-6pm at Gray’s Hall.  The show will be available for viewing until October 5th.  DJ Private Dancer aka @shane.levi will be spinning records. Stop by and buy cool art!

Backyard Shokz Demo Days

7:00 AM–12:30 PM | Special giveaways during 10–11 AM HYROX classes

Backyard is excited to welcome Shokz to the gym for two days of live demos! Come experience their game-changing bone conduction headphones that keep you connected to your music and your surroundings. Bonus: During our 10–11 AM HYROX classes each day, Shokz will host a special challenge. One lucky winner will score their very own pair of their brand new OpenFit 2+ headphones. This series is specifically designed for fitness scenarios to offer exceptional comfort.  You can learn more here. 

Live Music Round Up

A live DJ will be spinning at the XYZ bar at Aloft on D Street!  Enjoy a craft cocktail and snacks while you listen.

The Playwright – features DJ sets on Fridays and Saturdays starting at 9pm followed by Country Sundays with live bands starting at 6pm.  Check out the schedule here!

Park City – enjoy live music all weekend long!  Check out the schedule via Instagram here! 

Hunter’s – Friday 5-8pm, Saturday 1-4pm, and Sunday 3-6pm and 9pm-12am.  Follow Hunter’s on Instagram for their schedule!

Capo – In addition to Sinatra Sunday with Rich Dimare and the Ron Poster Trio on Sundays at 5pm, there are live bands and DJ sets on Fridays and Saturdays.  Follow Capo on Instagram for the schedule!

Lincoln – Legends of Summer on Sundays at 6pm.

Grace by Nia – features live music all weekend long!  You can check out the schedule here.

Loco –performers and DJ in the main space and the lounge on the weekend! Look on their Instagram story for lineup!

SPORTS!

Red Sox vs. Rays – Friday at 7:30, Saturday at 7:05pm and Sunday at 7:35pm.

Patriots vs. Steelers –Sunday at 1:00pm.

Here are 12 Places to Watch the Game in South Boston! 

Check out our New to the Neighborhood Guide

Welcome to the Neighborhood! Whether you just moved into the neighborhood or are looking for something new in the neighborhood, this is the guide for you! We’ve included helpful tips, new businesses on the horizon, and new things to try! It’s all right here! Check back as this guide will be updated!

Check back this list may be updated!