Weekend Picks – October 16th

Happy weekend!
The Style Exchange is back at The Anchor on Sunday
This Sunday, October 18th from 12-3pm, The Anchor is hosting the Style Exchange for another Community Thrift Market! Head over for some shopping and to see the fall displays at the outdoor bar.
Bring the kids to a Not-So-Spooky Storytime, Yoga, & Art class
On Sunday, October 18th from 10-1045am, 2 Mindful Girls are hosting a Halloween event at Henry Bear’s Park in Hood Park.
Celebrate Halloween the not-so-spooky way with a cozy morning of stories, movement, mindfulness, and creativity! Designed for children ages 3–8, this playful 45-minute class brings a Halloween-themed story to life through kid-friendly yoga poses, movement, breathing exercises, and imaginative play.
After our yoga adventure, children will create a special Halloween inspired art project to take home. This class is a wonderful way for little ones to build confidence, practice mindfulness, express their creativity, and enjoy the season together!
$15 per child, sign up now!
Olivia Rodrigo fans, head to Tall Ship for her merch pop-up
Tall Ship in Eastie is hosting Olivia Rodrigo’s Merch Pop-up from 12-7pm on Thursday, Saturday and Sunday. There will also be themed drink specials, bites, and her music playing as you enjoy Tall Ship!
Head to Baby Coachella at the Library, hosted by NEMPAC
This Friday, October 16th from 10-1045am, NEMPAC will be hosting Baby Coachella at the Library! Make sure you register at the front desk or online.
Try a Boxing Class for free!
Here’s 2 complimentary classes to TITLE Boxing Club at North Station – so go try a Boxing Class!
Charlestown, It’s Time to Get Spooky: Join our Halloween Decorating Contest & Give Back to Harvest on Vine!
Year after year, Charlestown just keeps upping the game when it comes to all things Halloween. Not only are there awesome annual, can’t-miss events and an epic evening of trick-or-treating, but people are also going all-out to decorate their buildings, stoops, and yards. Folks from all over the city are making their way over the bridge to take a stroll through these streets.
So, it’s time to up the game even more… with a decorating contest!
Here’s the deal:
- Sign up and pay the $20 entry fee. You get a small yard sign to display so people can vote, and the proceeds from your sign-up go towards supporting Harvest on Vine
- People will scan the QR code on your sign to view our Voting Form, and can vote for your address
- 1st, 2nd, and 3rd place winners get a Gift Card to Prima, Waverly, or Monument (your choice)!!!
Anyone can sign up – whether you have the time to create something out of a movie, or just have an array of pumpkins on your stoop and want to join in on the fun while supporting the community.
Tag us in your photos (@caughtincharlestown) so we can share your work with the community!
Try Prima’s October ‘Cocktail for a Cause’, which supports Breast Cancer Patients
Prima has announced their October ‘Cocktail for a Cause’ which supports the Ellie Fund. They provides essential, free support services that ease the daily burdens that breast cancer patients face. Here’s the drink:
Pink Ribbon Sour
- Tequila
- Sarti Rossa
- Vanilla
- Lime
- Egg white
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!
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.
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.
Here are 9 places to watch the game in the neighborhood!
Check back as this list may be updated. Thank you to our Caught in Charlestown readers and Neighborhood Partners for supporting our local journalism efforts!

Abbey is the face behind Caught in Charlestown. In 2023 she migrated from Southie to Charlestown and brought the spirit of the ‘Caught In’ community with her. She is a new momma, creator, real estate agent, yogi, and so much more.

5 Things You Should Know This Week – October 13th
Three Museums Offering Free Admission on Monday
Dust Off Your Dance Shoes! Disco Matinee Comes to Charlestown