4.9 min readBy Published On: October 19th, 2023Categories: See and Do0 Comments on Weekend Picks – October 20th

Need weekend plans? We got you covered. 

Bounce to The Bar

Join Barre by Jen at Stats for a 50-minute signature bounce and pulse class on Saturday, Oct. 21st at 9:15am. Enjoy an awesome workout followed by a Juneshine cocktail. Secure your spot here!

The Great Mr. Swindles Traveling Peculiarium

Get ready, Southie!  The Swindler is back in town! The Great Mr. Swindle’s Traveling Peculiarium and Drink-Ory Garden, the irreverent, outlandish and unpredictable traveling tented entertainment experience that won over Boston audiences last year, is returning to the Seaport District with a new show.  Audiences can look forward to new and unbelievable feats, bizarre comedy and other unexpected surprises on the grounds of Harpoon Brewery. The show will be running Friday, Saturday, and Sunday with shows at 5:30 and 7:30pm.  Tickets are on sale now — Purchase them here! Use the code CTN15 and receive 10% off – expires November 5th. 

Brunchtober at Publico

Publico has an awesome new fall brunch menu. The food items include a bag of donuts with pumpkin spice glaze, a pumpkin bagel with pumpkin cream cheese, and pumpkin spice french toast sticks with cinnamon butter, nutella, and maple syrup. The drinks are pumpkin cold brew, pumpkin spiced martini, and pumpkin season boozy frappe. YUMM! Make your reservation for this weekend here!

Last day for Pickleball at Lawn on D

Lawn on D is wrapping up pickleball for the season on Sunday, Oct. 22nd. The courts will be open from 12-7pm. Their concession stand will be open and they will have live music from 1-4pm. Reserve your spot for the court here!

Dog Costume Party 

Castle Island Brewery is hosting a dog costume party on Saturday, Oct. 21st from 11am-5pm. Bring your dog in their best costume to enjoy doggie cocktails and treats from Polkadog. The winner of the costume contest will win a gift basket from Red Dog! 

Self-Defense Training at Peter Welch’s Gym

Peter Welch Gym will be offering a self-defense training class on Sunday, Oct. 22nd at 12pm. The 60-minute class is $30 per person. The class will focus on mace training and situational awareness. Learn how to kick ass from the best ass kicker around!

Teen Fashion Night at the ICA 

The Teen Exhibitions Program, in collaboration with Boston Caribbean Fashion Week, presents Teen Fashion Night Out. The event will be held on Friday Oct. 20th from 6-8pm. There will be workshops led by fashion professionals to create upcycled wearable art, free snacks and beverages, and networking with each other and experts in beauty, culture, fashion, and style. This event is free for Teens 13+. Learn more here. 

Belly up to the bar with new fall drink specials

Shy Bird has new cozy drink specials! Including an Irish Coffee with Jameson, Demerara, Counter Culture Coffee, Crème Fraîche. And Mulled Cider with Local Cider, Laird’s Bonded, Housemade Warming Spices. 

Loco is getting into spooky season with their new fall cocktails available now through Oct. 31st.

The Monster Mash includes gin, ginger liqueur, lemon, blackberries, honey. The Witches Brew includes vanilla & pumpkin vodka, rumchata pumpkin, chocolat salted caramel liqueur, pumpkin puree, graham cracker rim. And last but not least the Grave Digger, which is frozen Bacardi dark, cazadores cafe, pumpkin puree, Irish creme liqueur, cold brew, black lava salt rim. 

Fall Fitness

As the weather gets colder and the couch starts looking a lot more comfortable, it may be time to switch up your workout routine for the fall season. Whether you are looking for group fitness around Southie or you prefer to exercise in the comfort of your own home, here are some options to keep your body moving. Check out our roundup! 

National Pizza Month

In honor of National Pizza Month– we’ve rounded up some of our favorite spots for pizza in the neighborhood! Boardwalk Pizza is all in! See specials below!

Family-friendly fun 

Babies and Brew

South Boston Moms Club presents Babies and Brew on Friday, Oct. 20th from 9-11am. It will be held at the playground at M Street Park. The event allows for parents to enjoy coffee and pastries with their babies. It is a great way to get to know fellow parents in your neighborhood. 

Daniel Tiger’s Neighborhood Live: King For A Day

Take a family field trip to Lynn for Daniel Tiger’s Neighborhood Live: King For A Day!. Based on the hit PBS KIDS TV show, is coming to the Lynn Memorial Auditorium this Saturday, October 21. Tickets starting at $27.00 plus applicable service fees are on sale now and are available at danieltigerlive.com or ticketmaster.com.

Fall-O-Ween Children’s Festival

The third annual Fall-o-Ween Children’s Festival will take place on the Boston Common Parade Ground at the corner of Beacon and Charles Streets on Friday, October 20, from 5 p.m. to 8 p.m. Adults and children are encouraged to wear Halloween costumes and participate in a wide range of free, fun, and spooky family-friendly activities. Test your courage in our Funhouse Maze and on the Spooky Mansion Slide, try the Jumpin’ Pumpkin, test your skills at the bean bag toss, and enjoy nighttime fun in our Glow in the Dark Park with LED swings, LED seesaw, and LED cornhole.

Live Music Roundup

Hunter’s: Stu Sinclair Friday at 9pm. Jimmy Westfall Saturday at 3pm. Matty Sheenan Sunday at 4pm and It’s Ya Boy KR Sunday at 9pm. 

Capo: Downstairs at the Supper Club, it’s DJ Silent Partner at 10pm, On Saturday, DJ Steny will be playing starting at 10pm, on Sunday enjoy Sintatra Sunday with Rich DiMare and The Ron Poster Trio!


-Patriots vs. Bills on Sunday, Oct. 22nd at 1pm. 

-Bruins vs. LA Kings on Saturday, Oct. 21nd at 10:30 pm. 

-Bruins vs. Ducks Sunday, Oct. 22nd at 8:30pm. 

Here are 12 spots to watch the game in the neighborhood! 

Check back! This list may be updated.

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