Need weekend plans!?! Check out our Weekend Picks!

Children’s Magical Halloween Castle Walk

In Southie, we are lucky enough to have our own castle (well, a historic fort), and it is the perfect setting for Children’s Magical Halloween Castle Walk. The celebration will be held on Saturday, October 24th and Sunday, October 25th from 12pm to 4pm. It is free and fun for all! Costumes are encouraged! Stop by Sully’s after for a hot dog! 

Park City Pumpkinfest

Park City is transforming into the perfect fall oasis for Halloween! The day will be filled with family fun! The event is happening on Sunday, October 25th from 1 to 4pm. Enjoy pumpkin painting, a costume contest, face painting, and more! The event is free, but RSVP here!

Get a Club Golden Membership

Club Golden is Southie’s newest spray tan destination! Memberships have officially dropped! Select either a single or double session package each month to fit your schedule. Perks include discounted member rates, priority scheduling, plus sweet VIP perks. Lock in your tier, grab your appointment, and keep that sunny glow all year long! Get all the details here!

PKL Family Halloween Event

On Saturday, October 24 from 1-4 p.m., PKL in Southie is hosting a Family Halloween event with free activities for kids and families, including pickleball, cornhole, a candy hunt for children ages 4 and under and a Halloween craft, where kids can make their own trick-or-treat bag. Throughout the event, PKL will have a dedicated pickleball court open for families to play for free from 1-4 p.m., with no reservation required. For adults, PKL will be serving Bloody Mary flights available for purchase during the event.

Draw Me Like One of Your Insiders

Just another reason to become a Seaport Insider VIP! On Saturday, October 25th from 11am to 2pm, you can get a hand drawn portrait. The portraits will be available at The Little Words Project. Not an Insider yet, sign up and enjoy all the perks! Get all the details here!

Fall Additions at The Broadway

Fall is here!! And The Broadway is ready with their fall menu!! The star being The Pumpkin Pie Espresso Martini with a chai cold foam and a biscoff cookie crumble!!! Make your reservations now!

Kings & Queens of The Court Volleyball Mixer

Head over to Club Volo at Assembly Row for a Singles Volleyball Speed Dating night, on Friday, October 23rd at 7pm! Whether you’re a pro or a total beginner, come out to serve, rally, and meet new people. Participants are divided into lines to be randomly paired into co-ed 2v2 teams for fast-paced, five-minute rounds where you’ll rotate partners after every match to ensure you get plenty of time to both play and socialize. Enjoy 60 minutes of volleyball followed by a social hour to keep the vibes going off the court. Sign up here!

Saturday AM Sweat Out at Moki

Kick off your Saturday morning with an invigorating sauna session! Enjoy upbeat music that will keep your energy high, alongside soothing hot sauna heat and refreshing cold plunge therapy. They are offering a great space to hang out, meet neighbors, and sip drinks between plunge rounds. On-site coffee will be served! Sign up here!

Hunt + Gather

Style Exchange is popping up at The Grove at Lawn on D on Saturday, October 24th, with clothing, shoes, and accessories from more than 50 local closets. Shoppers can browse secondhand fashion, vintage finds, and affordable pieces while supporting local sellers. Grab a drink at the bar and make it your own personal sip + shop! This event is free and open to the public.

Affordable Art Fair Boston

The Affordable Art Fair is coming to the South End, bringing together galleries and artists with original artwork at a range of prices. Whether you’re looking to add to your collection or just want to browse, it’s a fun way to discover new art and support artists. The fair takes place October 22nd–25th at SoWa Power Station, featuring more than 55 galleries and thousands of original works. General admission is $20. You can get tickets and more information here.

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 Saturdays.  Follow Capo on Instagram for the schedule!

Lincoln – DJ Sets starting at 10pm on Friday and Saturday. Rotating live bands 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!

Park City– Live music every night! Follow them for weekly lineup updates!

The Grove at Lawn on D– From DJ sets to live bands to line dancing! The Grove has a wide variety of entertainment throughout the week! Check out their schedule here!

Cisco Brewing Fenway – Check out the latest live music happening at Cisco Brewing Fenway here. 

SPORTS!

Bruins vs. Sharks – Saturday, October 24th at 7pm.

Celtics vs. Knicks – Friday, October 23rd at 7pm. 

MLB Playoff Schedule

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

Check back! This list may be updated! 

Have a fun-filled weekend! Thank you to our Caught in Southie readers and Neighborhood Partners for supporting our local neighborhood media efforts!