Need weekend plans!?! We got you covered with our Weekend Picks!

Late Night Laughs at The Seapoint

Catch Late Night Laughs at the Seapoint on Friday, October 9th at 10pm! Organized by Southie’s own Brendan O’Connell, the show features a fantastic roster of comedians, including Nic Ferreira, Lucan White, Alvaro Medoza, Katy Coughlin, and headliner Matt McArthur. Gather your crew, grab a drink, and get ready for a hilarious night out in the neighborhood! Tickets are $15—snag yours here! Use the code: SOUTHIE for $5 off! 

Tween Night at Clover Clubhouse

Join Clover Clubhouse on Friday from 6 to 9pm, for a special evening created specifically for girls ages 8-11! This drop-off gathering features a craft session hosted by The Crafty Girls, where participants can design two custom squishies to take home. The event also includes open play, dancing, and dinner! The perfect tween night! Sign up here!

Cheese & Wine Tasting at The Dirty Italian

The Dirty Italian are getting ready for the holidays by showcasing their new wine and cheese offerings! Stop by on Saturday, October 10th from 11 to 2pm. Southie Sourdough will be popping up as well! It is the perfect time to stock up and try some new items. They also are offering small charcuterie boxes to pair with wine! Sounds like the perfect hostess gift to me! 

Babies and Brew

South Boston Moms Club will host Babies and Brew on Friday, October 9th from 9 to 10:30am. It will be held at the playground at the Travel Mug in The Seaport. The event allows for parents to enjoy coffee and pastries with their babies. It is a great way to get to know the fellow parents in your neighborhood.  You can learn more here. 

Need a blowout? House of Ivy can help 

Sometimes you just want someone else to do your hair! Book a blowout at House of Ivy for date night, a wedding, an event, or simply because you feel like it. You can learn more here!

Seaport Book Fair

Book lovers, this one’s for you! The Boston Seaport Book Fair is happening on Saturday, October 10th, from 12pm–5pm at Harbor Way, featuring nearly 40 authors, booksellers, and specialty vendors. Browse books from independent, traditionally published, and children’s authors, shop local vendors, and maybe find your next great read. The afternoon will also include an author conversation with Heidi McLaughlin and Emma Zeiger of Ghosted by Grief, plus a reading corner at The Rocks where you can settle in with your new book. The Boston Seaport Book Fair is free to attend and takes place at 111 Harbor Way. Get all the details from Boston Seaport.

Fall Barista Drinks at Shy Bird

The new fall barista menu has dropped at Shy Bird! The menu features a Pumpkin Iced Latte, Apple Cinnamon Chai, and Brown Butter Salted Maple Latte. They all look and sound amazing! Stop by this weekend for brunch and try one! Secure your spot here!

$1 Wings at 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!

Boston Fire Aerial Drill Team Returns for Fire Prevention Week

One of Boston’s coolest Fire Prevention Week traditions is back! The Boston Fire Department Aerial Drill Team will be performing across the city this week, including a stop right here in Southie. Made up of Boston firefighters, the Aerial Drill Team performs impressive high-altitude rope and ladder maneuvers that showcase the skill, strength, teamwork, and trust required on the job. The tradition dates back decades and returned in 2024 after a roughly 20-year hiatus. Saturday, October 10 at Castle Island/Fort Independence at 11am.  Post-performance, grab some food at Sully’s!

Oktoberfest at Assembly Row with Volo

Ring in the autumn season alongside Volo, featuring endless entertainment, drinks, and live music! Challenge your friends to play pickleball, volleyball, cornhole, giant pong, pop-a-shot, Connect 4, or Jenga, with endless chances to win awesome prizes. Test your strength in a stein-hoisting contest, and score free swag from participating vendors and sponsors. Oktoberfest attire encouraged! Get all the details and tickets 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!

SPORTS!!:

Patriots vs.Raiders– Sunday, October 11th at 1pm. 

Bruins vs. Flyers – Saturday, October 10th at 1pm. 

Celtics vs. 76ers – Saturday, October 10th at 8pm. 

MLB Playoff Schedule

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!