4.7 min readBy Published On: May 16th, 2024Categories: See and Do0 Comments on Weekend Picks – May 17th

Need weekend plans?!?! We’ve got you covered!

Ride Your Bike to Work Day

Boston’s National Bike to Work Day Festival celebrates National Bike to Work Day. It’s our way of saying, “Thanks for riding your bike today.” The City wants to make it fun for experienced and new bike commuters by organizing convoys and a festival at City Hall from 7am-9pm on Friday, May 17th with free coffee and breakfast!  Southie Bikes is organizing a convoy from our neighborhood. Follow them on Instagram for the latest. 

Watch the USS Constitution Turn Around

The USS Constitution will be underway on Friday, leaving the Charlestown Navy Yard at 10am and heading to Castle Island’s Fort Independence for a 21-Gun -Salute around 11:30am. Great viewing spots include, the Charlestown Navy Yard, the Harbor Walk and Castle Island!

New to the Neighborhood: Small Victories

In the ever-changing landscape of restaurants and bars in Southie, there’s a new one in the neighborhood – Small Victories! Located at 400 Dorchester Street, this soon-to-be hot spot will feature a menu of delicious snacks like nachos, pickles, pretzels, chip + dip in addition to burgers, hot dogs, and more!  Plus, they’ll be serving up beer, wine, cocktails, and an extensive whiskey list! You can check out the full menu here! Small Victories is the sister restaurant to the wildly popular The Quiet Few in Eastie!

Taylor Swift Brunch at The Broadway

Get your friendship bracelets ready!  The Broadway is hosting a special Taylor Swift Brunch on Saturday, May 18th from 11am-2pm.  Enjoy a full DJ set, themed cocktails and food menu, videos, costume contest and of course, friendship bracelets.  Make your reservation here.

Seaport Smalls – Family Fun

Join Seaport Smalls on Saturdays, from 10AM-11AM outdoors at The Rocks at Harbor Way for a rotating selection of free children’s programming for ages 0-8 years old. Programming partners include Bonaparte Magic with magic, Little Groove Music, music for kids, and Porter Square Books with story hour. Refreshments will be available at Blue Bottle Coffee, including hot coffee, espresso beverages, and pastries. In the event of bad weather, Seaport Smalls will move indoors to The Paseo at 55 Pier 4 Blvd., where refreshments can be still purchased at Blue Bottle Coffee. Convenient parking can be found at the 111 Harbor Way Garage. You can check out the full schedule here! 

Pierogis, Polka + Polish Culture and History – Polish Fest 2024

Enjoy a day of culture, fun, food, drink, music + more! On Sunday, May 19th, from 12-6pmthe Polish American Citizens Club, and the Polish American Heritage and Community Foundation (PAHCF) will be hosting Polish Fest Boston 2024.  This family-friendly annual event allows people from all over the greater Boston area to enjoy the warm hospitality of the Polish community.  This event will feature The Baltic Poka Band, DJ Mariusz Wierzibicki, Krakowiak Polish Dancers of Boston, plus vendors, artisans, food, and beer!   The event is located just a six-minute walk from Andrew Square Station (Red Line) and the #16, #17, #18, #10, and #5 buses.

Booty by Brabants x PKL Pickleball Tournament

Sunday Funday is in full swing at PKL on Sunday, May 19th, from 10am to 1pm. Booty by Brabants will be hosting a pickleball tournament featuring a DJ, light bites, a cash bar, and a Booty by Brabants trunk show! There are tickets for those interested in the tournament and those who just want to watch and enjoy the fun! Get tickets and more info here!

Dirty Water Donut Shop Pop-up at L Street Tavern

Dirty Water Donut Shop is a Boston-based clothing brand that has awesome merch to show your Boston pride! They will be at L Street Tavern on Saturday, May 18th! It is the perfect excuse to buy a sweatshirt or hat and a couple of drinks! Check out their website here! 

Next Stop Comedy Stand-Up Show

Castle Island Brewery will be hosting Next Stop Comedy on Friday May 17th from 8-9:30pm. Next Stop Comedy showcases professional comedians from Boston, New York City and beyond! Each show features a novel line-up with acts seen on TV and heard on your favorite podcasts. Get your tickets here!

Irish American Society Boston Detective Tour

Calling all true crime enthusiasts!  The South Boston Irish American Society is hosting a fun filled day with a trip aboard the Boston Detective Tours – a true crime tour of some of Boston’s most famous cases with retired BPD Detective Joe Leeman! Cost is $35 and it leaves from the Seapoint!  To reserve your spot, you can message The South Boston Irish American Society via Instagram. 

Live Music Roundup

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! 

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 Saturday.  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 has performers and DJ in the main space and the lounge on the weekend! Look on their Instagram story for lineup!


Bruins vs. Panthers on Friday at 7pm and Sunday TBD

The Red Sox face the Cardinals this weekend on Friday at 8:15pm, Saturday at 7:15pm and Sunday at 1:05pm.

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

Check back as this list may be update!



Leave A Comment