4.5 min readBy Published On: September 21st, 2023Categories: See and Do0 Comments on Weekend Picks – September 22nd

Need weekend plans?

23rd Annual South Boston Street Festival – Postponed due to rain

Thanks to Hurricane Lee, the street festival was postponed last week! Well, the highly anticipated 23rd South Boston Street Fest will take place on Saturday! East Broadway between I and L streets will be transformed into a vibrant and lively hub of festivities from 11 a.m. to 4 p.m. Get all the fun details here! 

Castle Island 2nd Anniversary Party

Castle Island Brewery and Bardo’s are hosting a Homecoming in honor of their 2nd Anniversary in South Boston. Join them for pep rally games, new pizza and beer specials, and a DJ from 4-7PM. The event will be Saturday, September 23rd, from 11am to 11:30pm. 

South Boston Youth Hockey Kick Off The Season Event

Join South Boston Youth Hockey at the Lawn on D for a celebration of the start of their season. They will have raffles and music. The event will be held on Saturday, September 23rd, from 4-9 PM. The tickets are 30$ and kids are free with a paying adult. Grab your tickets here. 

The LOT On the Dot Movie Night 

Over the fall and winter of 2023, The LOT On the Dot will host a series of public events for the South Boston community and surrounding areas, inviting everyone to come together and enjoy the newly developed space. The fun kicks off on Friday with a Movie Night at 5:30pm featuring The Lion King, complete with free popcorn and cotton candy, plus food trucks and adult beverages! You can learn more here!

Boston By foot Walking Tour

Join Boston by Foot on Saturday Sept. 23rd from 1 to 2:30pm to learn about the history of South Boston. The walk will start at the corner of West Broadway and D Street and end at M Street Park. You may be surprised to learn that something you see every day has historical importance. Tickets are $16 for adults, $9 for kids 6-12, and kids under 6 are free. You can reserve your spot here! 

Seaport x Black Owned Bos. Market

Seaport x Black Owned Bos. Market is back with over 50 vendors.   From gifts and apparel to packaged foods and beauty & skincare products, the Seaport x Black Owned Bos. The market offers something for everyone as it raises awareness for and support of Black entrepreneurship.  Come support your local black-owned businesses! Takes place on Sunday Sept. 24th from 12pm-6pm. You can learn more here. 

Golden Hour at Fresh

Golden Hour at Fresh takes place on Tuesdays-Saturdays 4p-6p Dine in only $4 draft beers, $10 buckets of corona & miller high life grenades, $6 Fresh Margaritas, $6 golden hour ju ju juice, plus a bunch of food specials, all $10 and under! Nice!

DJ Pauly D Takeover

YEAAAH BUDDY!! Spend your Friday Sept. 22nd, with DJ Pauly D on both land and sea. Join DJ Pauly D on the high seas from 6PM to 10PM. The boat departs from 200 Seaport BLVD. If that’s not enough Pauly D for you, join him at The Grand. Doors open at 9:30PM. Get tickets for both here!

PKL Pickleball Open

PKL is hosting a tournament on Saturday, September 23rd from 9am to 12pm. The tournament will have 20 teams of 2 from beginner to intermediate. The ticket includes 2 drinks. And don’t worry if you get eliminated. They will have open courts for open play. Get your tickets here.

Sunday Walk with Boston Girls Who Walk

Hot girl walk around the Seaport with Boston Girls Who Walk. The group will be meeting at Fan Pier in the Seaport Sunday Sept. 24th at 11:30am. The walk will end at the Lawn on D for the Modern Markets

Hispanic Heritage Month in the Seaport

Head on over to the Seaport to celebrate Hispanic Heritage Month. Shop at Little Words Project or discover custom cocktails at Borrachito, Para Maria, Scorpion Bar and Vela. All of these businesses have come together with a unique offering for Hispanic Heritage Month. Seaport will donate $1 per item sold at our Latin-owned businesses to Sociedad Latina. Find out more here

Workouts to Try in the Neighborhood

Shake up your workout routine by trying something new! Check out our roundup! 

Live Music Roundup

Hunter’s: Friday at 5PM, Eric Jalajas. Saturday at 3PM, John Dillon. Sunday at 2PM, Matty Sheehan and It’s Ya Boy KR at 9PM

Capo Supper Club: Friday at 7pm, The One Night Stands. Saturday at 8PM, DJ Silent Partner. Sinatra Sunday at 5pm with Rich Dimare and the Ron Poster Trio. 

Loco: Spend your game day at the Loco Lounge Sunday at 1-5PM, DJ Bryceworthy and 5-9PM DJ Brekone.  Guess what? Pitchers of margaritas will be available on Sundays! 

Shamrock Pub: Jinty McGrath will be playing live after Rugby matches at Shamrock from 5pm-8pm on Saturday!

Patriots vs. the Jets

The Patriots will face the Jets on Sunday at 1pm.  Expect Southie to be bananas. Here are 12 spots to watch the game in the neighborhood! 

New to the Neighborhood Guide

Southie is my hometown!   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 as this list may be updated! 


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