Need weekend plans!?! Check out our weekend picks! It is a big weekend with the Kentucky Derby and Cinco de Mayo celebrations.

SBMC First Annual Derby Day Gala

South Boston Mom’s Club is hosting their 1st Annual Derby Day Gala on Saturday, May 3rd from 5 to 9pm. This event will help fundraise for their Southie Family Fun Day. The ticket is $50 and includes a drink and passed hors d’oeuvres. Make sure to wear your Derby best! Get your tickets here!

Camp Current Opening Weekend

The Current returns to Boston Seaport, transforming into Camp Current for the Summer 2025 season. It is opening May 1st and will run through August 31st. Camp Current and its nine curated brands invite guests to shop, savor and rediscover the joy of carefree summer days. The featured brands are Coastal Caviar, illesteva, Facecard Skincare, Nantucket Crisps, Megababe, Gus & Ruby, The Hyppo Gourmet Ice Pops, and 1987. They will be having a grand opening party, Friday May 2nd from 4 to 6pm. Make sure to stop by!

The Return of the Lawn on D

The Lawn on D is back for a new season starting Friday, May 2nd for the 2025 season! Gates are regularly open 7 am – 11 pm Monday through Saturday and 7 am – 10:30 pm on Sunday. Food, drinks, and lawn games are regularly available Thursdays through Sundays. Plus live music, special events and more! Plus FREE pickleball! Check out the full schedule here. 

South Boston Irish American Society Sunday Funday

Sunday Funday just got even better!! South Boston Irish American Society is hosting a Sunday Funday at Fat Baby on May 4th from 2 to 6pm. It is for existing and anyone interested in becoming a member. It is a great way to get involved in the community!

The Point Clothing Lounge is Derby Attire Headquarters

Still need something dapper to wear to that Kentucky Derby Party? Stop by The Point Clothing Lounge – they can help you out!

Blooms & Buttercream

Publico and The Sugar Connection Bakeshop are teaming up for a spring cake decorating class. The class will be held on Saturday, May 3rd at 12pm. You will learn all the techniques to make the perfect spring cake! Get your tickets here!

Recover & Recharge: An Athletic Wellness Pop-up at You vs. You

You vs. You and Belamour Aesthetics will be hosting a wellness pop-up on May 3rd from 11am to 2pm. There will be mini facials, leg compression therapy, and more! It is an ultimate self care day! Sign up here!

Taco Eating Contest at Loco

Join Loco for a Taco Eating Contest to celebrate Cinco de Mayo! It will be held on Friday, May 2nd at 5:30pm in The Lounge. It is $100 for a 4 person team and there will be 3, 3 minute, rounds! Come hungry to eat as many tacos as you can! There will be prizes for 1st, 2nd, and 3rd! Get all the details and sign up here!

Tacos, Tunes & Tinlin: Fourth Fest Returns

The Fourth Presbyterian Church Fourth Fest will take place on Sunday, May 4, from 2:30 p.m. to 5:30 p.m., at Southline, 1135 William T. Morrissey.  Get all the fun details here! 

May the Fourth

XYZ Lounge at Aloft is hosting a Star Wars Marathon all day on May the Fourth! Stop by for a cocktail!

Take a hike!

Boston Walking City Trails has launched a brand new hiking trail!  The City on the Hills Trail is a 31-mile adventure through some of the best parts of the city. And because we love a good walk (especially if there’s a view and maybe a snack involved), we’re breaking it all down for you, section by section – starting with Trail #5 – Dorchester to Southie – get all the details here! 

Healing Through Live Music: A Soulful Journey at Summer Street Wellness

Live music has a profound ability to heal and restore. Music, especially when performed live, creates a space where your body and mind can synchronize with the rhythm, leading to a heightened sense of well-being. This Sunday, Summer Street Wellness is hosting a Live Violin + Vibrations Restorative Yoga and Reiki event from 4pm-5pm for $25.  You can register here! 

Bagel Brunch Open House

The Carlisle Group is hosting a Bagel Brunch on Saturday featuring bagels, bubbles + city views at 405 W. First Street, Unit 303 at 10am!  You can learn more here! 

SoWa Opening Weekend

Sunday is SoWa’s opening day for the open market, which runs from 11 a.m. to 5 p.m. Artisans, craftspeople, designers, and local farmers gather in the SoWa Open Market, where shop owners open their doors. There is live music and food trucks. Stop by and support the awesome small business owners.

Live Music Round Up

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 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!

Kentucky Derby at 6:30pm

Red Sox vs. Twins – Friday, May 2nd at 7:10pm, Saturday, May 3rd at 4:10pm, Sunday, May 4th at 1:35pm

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

Check back as this list may be updated.