Weekend Picks – October 16, 2026

6 min readBy Published On: October 15th, 2026Categories: See and Do0 Comments on Weekend Picks – October 16, 2026

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

SB Moms Club x MyStryde Mom + Me Strength

Calling all mamas, expectant mothers, and little ones! MyStryde is partnering with SB Moms Club for a mat-based full-body strength class. Enjoy functional exercises, core training, and modifications tailored for pre- and postpartum fitness. Move your body and bond with local moms—babies welcome! The Session runs on Friday, October 16th at 11:30am at MyStryde Southie

Fort Point Open Studios

Meet more than 110 local and visiting artists showcasing everything from paintings and photography to sculpture, jewelry, and more. Plus, enjoy live music, pop-up exhibits, and free hands-on art workshops for all ages. It’s a great way to explore the neighborhood and support local artists! When: Friday, October 16th, 4pm–7pm, and Saturday and Sunday, October 17th–18th, 12pm–6pm. Admission is FREE! You can get all the details, including participating locations, here.

Boston Rodeo & Music Festival

The Rodeo is in town!! Yes, you read that right! More over Texas, Southie has it all! Catch top-tier PRCA pro rodeo action right in the Seaport for two action-packed days! Expect high-energy bull riding, barrel racing, team roping, plus tons of live tunes, art, and delicious bites across the venue! Get all the details and tickets here!

Help Clean Up Moakley Park

Show Moakley Park some love! Join Boston Harbor Now, South Boston en Acción, Boston Parks and Recreation, and Boston Cares for a community cleanup on Saturday, October 17th, from 9:30am–11:30am. It’s a great way to give back, enjoy some fresh air, and help keep our neighborhood looking its best! Get all the details here.

Sweater Weather Fest at City Hall Plaza

The first-ever Sweater Weather Fest takes over City Hall Plaza on Saturday, October 17th, from 2pm–11pm! This FREE festival features live DJs, film screenings, local food vendors, industry panels, and plenty of fall fun! Plus, the evening wraps up with a screening of the final two episodes of Apple TV’s Widow’s Bay on a giant outdoor screen. Bring a blanket, grab some cider doughnuts, and enjoy a fun fall day in Boston! You can learn more and RSVP here.

Lunch at Lucky’s Lounge

Lucky’s is open Monday to Friday for lunch and serves food till 1:30am Monday through Saturday! The steak & cheese at Lucky’s is to die for! Check them out this Friday for lunch to kick off the weekend. Make your reservation here!

Spooky Seaport Smalls

Head over to Seaport Smalls on Sunday, October 18th from 10am to 1pm for a hauntingly fun time! The little ones can dance to Halloween tunes with Little Groove, followed by endless goodies! There will be cotton candy, frozen hot chocolate, a photo booth, balloon artists, festive handprint crafts, and so much more! Plus, grab your costume and trick-or-treat through more than 30 participating local spots! Get all the details here!

Sunday Sweat at Loco Lounge

Sunday Sweat is taking over The Loco Lounge for a group sculpt class on Sunday, October 18th at 10am. Barry’s  instructor Kiley Chase will be leading the 45 minute HIIT, which is a great full body workout! The tickets include the class, a mimosa, and complimentary patatas bravas! Get your tickets here! Don’t forget to bring your own mat!

Beignet Bar Cart at Publico

You heard that right…a Beignet Bar Cart at Publico Brunch! It kicks off Saturday, September 19th. The flavors include Nutella Crunch, Bourbon Caramel, Cookies & Cream, S’mores, and Cinnamon Toast, all served tableside. Secure your spot now!

Bardo’s Football Promo

Score awesome specials all football season during every Sunday Pats game! Order any two pizzas and grab half-off an order of wings with your favorite sauce! Upgrade your wings with a $4 sauce flight featuring Sriracha Aioli, Buffalo, Thai Chili, Pickle Ranch, and Blue Cheese! Order yours here!

Oktoberfest at Castle Island Brewery

Grab your Lederhosen & Dirndls! Castle Island Brewery is celebrating Oktoberfest season in Southie. All day, Saturday, they will be serving up pours of your favorite German Lagers,Make Your Own Pretzel Necklace, Bierstacheln (Hot Beer Poking), and plenty of Umpah Music! Reserve your spot here!

Let Sully’s Cater Your Party

Skip the kitchen hassle this weekend! Sully’s has you covered. Whether you are hosting a birthday bash, gathering with family, planning a work lunch, or feeding a big crew, let Sullivan’s handle the food! Get all the info here!

Get a Sweet Treat at Bottega

The neighborhood’s best hidden gem for sweet treats is tucked away right here in Southie! From rich layered cakes and traditional tiramisu to crisp cannolis, Bottega del Sud has a case overflowing with incredible options that will instantly brighten your day! Take this as your official sign to grab a treat and swing by Bottega!

80s Darling at Marcelino’s

Marcelino’s is throwing it back on Sundays! They will be spinning the sounds of the 80s and 90s starting at 8pm. Head over to Marcelino’s to relive the golden eras of music and keep the weekend vibes going strong! Reserve your table here!

Boston Book Festival

The Boston Book Festival is taking over Copley Square this weekend! The free main festival happens Saturday, October 17th—plus a ticketed preview event on Friday night! Browse 80 events featuring over 200 amazing authors. Build your ideal day with keynotes, creative workshops, guided walking tours, and tons of fun activities while discovering top literary talents! Check out the complete event lineup 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!

Patriots vs. Jets– Sunday, October 18th at 1pm. 

Bruins vs. Ducks – Friday, October 16th at 10pm. 

Bruins vs. Kings – Saturday, October 17th at 9pm.

Celtics vs. 76ers – Friday, October 16th 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!

 

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