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

Halfway to St. Patrick’s Day

Castle Island Brewing is hosting a Halfway to St. Patrick’s Day bash! The event will be held Saturday, October 3rd at 12pm. They will have live music featuring Forfocséic and Kier Byrnes. Wear green to match your green beer! Get tickets here!

Tumble Tots at Clover Clubhouse

Calling all little ones! Clover Clubhouse is hosting Tumble Tots on Saturday, October 3rd at 10:15 am. It’s an energetic session designed to help toddlers roll, jump, and build balance, coordination, and fundamental gymnastics skills. It’s a wonderful way for preschoolers to develop confidence and stay active through interactive, playful exercises in a supportive setup! Sign up here!

Yacht Rock Sundays at Park City

The sweet sounds of Yacht Rock will be taking over Park City on Sunday, October 4th. The Blue Light Bandits will be performing from 5-8pm. The drinks will be flowing! Their fall menu also dropped including amazing additions. Stop by for an awesome time! Nautical outfits encouraged…by me haha. 

Fall Fest (Taylor’s Version)

Calling all Swifties! The Lawn on D is hosting Fall Fest (Taylor’s Version) on Saturday, October 3rd from 12pm-5pm! Rock your favorite era outfit and spend the afternoon enjoying friendship bracelet making, face-painting, and a live Taylor Swift tribute show by Anna Daley Young from 2pm-5pm. Plus, check out ear-piercing with Nurse Cassandra @thisnursetravels2u and shopping with COSMO CAPRI @shopcosmocapri! Admission is free, with food and drink available to buy. Get more info here!

Lunch at Mother’s East

Make your weekend lunch plans at Mother’s East Tavern! The Southie neighborhood pub features its legendary Smash Burger and hand-cut fries, fresh oysters, fish + chips, plus plenty of great cocktails to go with it. Located at 289 Dorchester Street, it’s a cozy spot to grab a bite and settle in for the afternoon.

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! Sessions run on Fridays, Starting October 2nd at 11:30am at MyStryde Southie

Wine & Za at Petula’s

Sundays just got better!! Petula’s is offering a deal of a bottle of wine and your choice of pizza for $55. It will be happening every Sunday from 4 to close. Make sure to get the cookie skillet for a complete balanced dinner! Make your reservation now!

Hawksmoor Sunday Roast

Make Sunday dinner extra delicious with the Sunday Roast at Hawksmoor in Fort Point. Enjoy slow-roasted beef with all the fixings, including crispy roast potatoes, Yorkshire pudding, veggies, and plenty of gravy. It’s cozy, hearty, and a perfect way to wrap up the weekend! Make your reservation today. 

Blessing of the Animals

In honor of the feast of St. Francis of Assisi, Patron Saint of Animals, all are welcome to the Annual Blessing of the Animals that will take place on Sunday, October 4, 2026, outside of Gate of Heaven Church, downstairs in the I Street Courtyard, near the Celtic Cross, following the 12 Noon Mass at 1PM. Please have your lovable family pet on a leash or in a pet carrier.

Cocktail for a Cause at Maple & Ash

All throughout October, Maple & Ash over in the Seaport is serving up a special drink for Breast Cancer Awareness Month! Order the Second Chances—a delicious blend of Grey Goose, housemade fig vermouth, spiced pear, cranberry-apple, and citrus. For every drink sold, Maple & Ash is donating $2 to The Ellie Fund alongside Bacardi Limited. Sip for a good cause! Make your reservations here!

Shredding Event at Mass Bay Credit Union

Time to Shred! Have a pile of old bills, statements, or paperwork taking up space? Mass Bay Credit Union is hosting a FREE Shred Day on Saturday, October 3rd from 9am–12pm at its South Boston branch. Bring up to five boxes of documents, and they’ll take care of the shredding for you. Easy, free, and a good excuse to finally clean out that file cabinet! Get all the details on the Mass Bay Credit Union website.

Fermenting Class at The Block

Master the art of preserving seasonal produce in this hands-on workshop! You’ll learn easy-to-follow techniques that you can seamlessly recreate right in your own kitchen. Guests can look forward to light bites along with a curated spread featuring Woods Hill Farm charcuterie and award-winning raw milk cheeses courtesy of our trusted farm partners! You’ll head home with your very own homemade Dilly Beans and Kimchi, plus all the confidence you need to keep fermenting at home! Get tickets here!

Maker/Scholar Office Hours at The Current

Head over to For Now at The Current on Friday, October 2nd from 4 to 6pm for Maker/Scholar Office Hours. Choose an item and get it hand-painted with either an oyster, lobster, or cocktail. It is first come, first serve so make sure you get there early. I am personally eyeing the journal with a cocktail on the front! Follow them on Instagram for updates

It’s Oktoberfest Season

Get your lederhosen and beer steins ready! This October, Boston has fun festivals and unique beers galore!  Check out our roundup, including Harpoon, The Anchor, and Dorchester Brewing!

Style Exchange Thrift Event in Southie

Style Exchange is popping up at Native Sun Dispensary South Boston on Sunday, October 4th from 11am–2pm for a Southie thrift market. Browse 50+ racks filled with clothes straight from your neighbors’ closets and score some new-to-you finds without breaking the bank. It’s free to shop, and the event is 21+. Get all the details 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 Seaport features a rotating lineup every weekend. Follow them for their schedule.

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

SPORTS

Patriots vs. Bills – Sunday, October 4th at 1pm. 

Bruins vs. Jets – Friday, October 2nd at 8pm. 

Bruins vs. Wild – Saturday, October 3rd at 8pm. 

MLB Playoffs 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!