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

Grand Tasting at The Gallery Liquor + Wine with a Country Twist

Get your cowboy hats and boots ready for the first Friday of fall in Southie! The Gallery Liquor + Wine is hosting a special Grand Fall Tasting on Friday, September 27th, from 5pm-8pm with over 100 products to sample, including wine, beer, and spirits, on two levels! This event will be a Wild West theme, complete with country music, snacks, glassware, and a tasting booklet!

Best Dressed Country Look will go home with $250 Cash!  Yeehaw!

Brands featured at this event will include Don Fulano, Fisher’s Island, all things pumpkin spice, fall reds, unique white wines, orange wine, and ready-to-drink cocktails!

24th Annual South Boston Street Festival

The street festival will be held on Saturday, September 28th, from 11 to 4pm. The event takes over East Broadway from L to I Street. Building on a rich tradition, the 2024 Street Fest is set to be the biggest yet, with nearly 100 local businesses, artists, and community organizations participating, along with many of the neighborhood’s top restaurants. With more than 5,000 attendees expected throughout the day, the event has solidified its place as a beloved community tradition. There will be shopping, music, fun activities, and more!  It is the perfect way to enjoy a fall Saturday and support the community! Get all the details here!

PKL Oktoberfest

Celebrate Oktoberfest at PKL, this Saturday September 28th from 2-7pm. The main event will be a beer pong tournament, tickets are $25 for two people and includes two beers! Check in for the beer pong tournament is 1:30pm. Also enjoy a stein hoisting competition and live music! Get all the details here!

Sunday Sweat at Loco Lounge

Sunday Sweat is taking over The Loco Lounge for a group pilates class on Sunday, September 28th at 10am. Kelsey Morse will be leading the 45 minute mat pilates class, which is a great full body workout. The tickets are $25 and include the class, a mimosa bar, and a free brunch when you stay for brunch after! Get your tickets here!

Lace up your sneakers – participate in the Colin’s Joy Project 5K

The Annual Colin Joy Project 5K will take place on September 28, 2024 at 9am. The day will begin with two youth races, followed by a 5 km course along scenic South Boston beaches. After the race, there will be light refreshments and entertainment, along with the awards. Don’t forget an opportunity to grab Colin’s Joy Project merch! Colin’s Joy Project race shirt to be given to the first 250 registered 5K runners/walkers.

Youth Races:
8:15 am. – 100 Meter Dash (9 years and under)
8:30 a.m. – ½ Mile Race (14 years and under)
* 5k open to all ages for the walk or run*

5K Registration $30 – Youth registration $15  – Register here! 

Flea Market at The LOT

On the Dot® is hosting its first flea market at The LOT on September 28th from 12-5PM. A day filled with local shopping, delicious food, and great company! Vendors include Alice The Potter, Fanny’s Handmade Soaps, PIA, Michaelas Market, and more! As always, admission is FREE but be sure to RSVP here. First 100 customers arrived will receive a limited edition LOT tote bag! Food will also be provided from Northeast of the Border and Crepe Shop for when you need a snack or meal after shopping!

Girls Brunch at Publico

On Sunday, September 28th, Publico is hosting a special Girls Brunch! Saturdays may be for the boys, but SUNDAYS are for the Girls. Reserve your table to the all new #FORTHEGIRLS Brunch Party kicking off in the Garden from 10am to 3pm. Reserve your table for brunch and enjoy not only our regular brunch classics, but a specialty cocktail menu like none-other, especially crafted for the girls, special brunch treats, shopping, pampering and fun from local vendors. Secure your spot here! And stay for the Pats game at 4pm!

Bardo’s Pizza Making Workshop

Head over to Castle Island Brewery for a Bardo’s pizza making workshop, on Sunday September 28th from 11am-1pm. Create your masterpiece and The Bardo’s Chefs will cook it for you! The event is 21+!  The ticket includes a personal pizza pan, pizza ingredients, and a chef’s hat. There is also a gluten free kit available! Get your tickets here!

$1 Wings at The Shamrock Pub

The Patriots are playing Sunday and The Shamrock is the perfect place to watch the game. And to make it even better they are serving $1 wings, (6 wings minimum per order). For more updates, follow them on instagram!

Picnic at M Street Park

South Boston Moms Club is inviting families with kids of all ages to join them for a picnic! The picnic is Sunday September 29th from 11-1pm. It will be held at the Medal of Honor Playground. Capo will be providing treats and coffee! A great way to hangout with old and new friends.

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!

Shamrock Pub has live music on Fridays with Fionn starting at 8pm

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 has 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 September 27th at 7pm, Saturday September 28th at 4pm, and Sunday September 29th at 3pm.

Patriots vs. 49ers – Sunday September 29th at 4pm.

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