5 min readBy Published On: September 15th, 2022Categories: See and Do0 Comments on Weekend Picks – September 16th

South Boston Street Festival

The South Boston Chamber of Commerce, in partnership with the South Boston Neighborhood Development Corporation, is pleased to announce the 22nd South Boston Street Fest, which will take place Saturday, Sept. 17, 2022, from 11 a.m.-4 p.m. on East Broadway between I and L streets. There will be shopping, food/drink and live entertainment.  Get the full details here! 

Half-Way to St. Paddy’s Day Party

Join 02127 Promotions as they count down to St. Paddy’s Day! All net profits will be donated to the SBAWVC 2023 Evacuation Day/St. Patrick’s Day Parade! This fun event will take place on Saturday, September 17th at 7pm at Florian Hall. Devri “Boston’s Irish Band” along with DJ Sean O’Toole will be the live entertainment! Tickets are $25 and can be purchased here! 

Pour + Paint at C Street Pop Up

On Friday from 4pm-8pm at C Street Pop Up enjoy an evening of Pour + Paint with local artist Rahim Gray! 

Telegraph Hill now features Brunch

Every Saturday and Sunday Telegraph Hill will be hosting brunch from 11am-3pm.  They will also screen all of the college and NFL games on their 11 screens.  For details about their new brunch menu visit here. 

New Cocktail to Try at Shamrock Pub

Enjoy the Boston Strangler made with Casamigos Tequila, black current, ginger beer and lime. Or how about something a little seasonal – BAE’s PSL with espresso vodka, kahlua, pumpkin spice cream, ice with a cinnamon stick. You can check out the Shamrock’s new cocktail menu here! 

Boston Firefighter’s Local 718’s Oktoberfest

SoulCyle + Seaport + Sunset

Join SoulCyle PORT on Friday, September 16th for an evening outdoor class at 5pm and 6pm at Seaport Common – next to The Current.  You can learn more here! 

Pick some Apples

Venture out of Southie and pick yourself a bushel and peck of farm fresh apples. Make sure to check check all orchard’s websites for up to date safety info, restrictions etc. Some require reservations so double check before you head out! Here are our picks for 5 Places To Pick Your Own Apples! 

Lawn on D – Full Swing

The Lawn on D will be in full-swing this weekend! Food, games, and live music all weekend.  Check out the schedule here! 

Sip a Negroni

Bar Volpe is celebrating Negroni Week! Whether you love a classic negroni, a sbagliato, or a mezcal negroni  celebrate with Bar Volpe. They’ve got all your favorite negronis and more and they’ll will be mixing up fun variations all week long. Plus $1 of every Negroni flight purchased goes to a great cause @transequalitynow

Free Ferry to Spectacle Island

In September and October, Save the Harbor/Save the Bay will host three free day trips to Spectacle Island from 10am – 2:30PM on Sunday September 18th, Sunday September 25th, and Sunday October 2nd. They will also host three free Sunset Cruises towards Boston Light from 5:30pm – 7:30pm on Tuesday September 27th, Wednesday September 28th, and Saturday October 15th. You can reserve your spot here! 

Live Music

Loco will feature DJ Colin Tonge on Friday at 9pm, DJ Mike D on Saturday at 9 and on Sunday it’s Big Party Orchestra.

Hunter’s will have Jimmy Tunes on Friday from 4pm-7pm, Dylan Burke on Saturday from 3pm-6pm and on Sunday Anna Daley Young will play from 2pm-5pm and Matty Sheehan from 9pm-12pm.

Castle Island Brewing will have HillBilly Holiday on Friday night at 8pm.

C Street Pop Up at Iron Works will feature Linsay by Boston Music Project from 6pm-7pm on Friday.

Lincoln – Enjoy Summer Fridays with a live DJ and $1 oysters from 1-4pm and on Sunday – Legends 6-9pm

Capo will feature Different Strokes on Friday from 8-11pm, Saturday it’s Johnny Dow 8-1am and Sunday Sunday it’s Sinatra Sunday with Rich Dimare and Ron Poster Trio

Flower Hour at The Wild One

Enjoy some creativity at C Street Pop Up with the Wild One – Flower Hour!  It’s like Happy Hour, but better.  Enjoy an evening of playing with flowers and sipping on delicious bevvies.  Here’s how it works:

  • Arrive anytime between 5-8PM.  The floral arranging takes around 35-45 minutes, so we recommend arriving no later than 7PM.
  • Pick up your bloom bundle, vase, scissors, instructions to make a self-guided centerpiece, and glass of Wölffer Estate Cider Rosé (NA options available and are the same price)
  • Find a seat, read the instructions and get to Blooming & Boozing!
  • Staff members will be walking around to assist as needed!
  • One drink is included in the ticket price, but we highly encourage you to stay for more :).

Reserve your spot here! 

41st Anniversary of South Boston Vietnam Memorial

South Boston Vietnam Veterans will celebrate the 41st Anniversary of the South Boston Vietnam Memorial, located in Medal of Honor Park on East Broadway, on Sunday, Sept. 18, 2022 USS Constitution Commander Billie J. Farrell, U.S. Navy, will be the keynote speaker. A Memorial Mass will be held in St. Brigid Church, 841 East Broadway, South Boston, at 10:30 a.m., followed by an 11:30 a.m. rededication ceremony at the memorial.

NFL Football Sundays in Southie

The Pats face the Steelers on Sunday at 1pm.  Here are 10 Places to Watch the Game in Southie! 

Outdoor Workouts to Try

Summer’s the perfect time to ditch your gym membership and get your sweat on outside. From beach yoga to backyard bootcamp, no matter what kind of activity you’re into, we have an awesome outdoor class for you! Check out our roundup here !

Check out our New to the Neighborhood Guide

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 list may be updated. 








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