Fall-O-Ween Children’s Festival
Mayor Michelle Wu and the Boston Parks and Recreation Department will host the fourth annual Fall-o-Ween Children’s Festival on the Boston Common Parade Ground at the corner of Beacon and Charles Streets on Friday, October 17, from 5 p.m. to 8 p.m. Get all the details here!
Adams Village Fall Fest is almost here! 🍁
On Saturday, October 18th, from 12–5 PM, enjoy a day full of fun in the heart of Adams Village!
✨ Shop and support local businesses & vendors
✨ Enjoy bites from amazing local restaurants
✨ Kid-friendly activities + face painting
✨ Music, raffles, and get your picture taken by a photographer at our fall-themed photo booth
This event is organized by Fringe Boutique and Everything Adams Village!
Fort Point Open Studio Turns 45
The Fort Point Arts Community (FPAC) is once again opening its doors for Open Studios weekend! Step inside the historic artist warehouses and meet more than 100 local and visiting artists showing off their work — from paintings and photography to sculpture, jewelry, and beyond. Enjoy live music, pop-up exhibits, and free hands-on workshops throughout the weekend. It’s the perfect excuse to stroll the neighborhood and support local artists. They will be open Friday, October 17th from 4-7pm, Saturday, October 18th and Sunday, October 19th from 12-6pm.
Play It By Fear
The Seaport and Castle Island Brewing are teaming up to host an awesome Halloween concert on Friday, October 17th from 6:30 to 8:30pm. There will be vendors, food, and even tarot card readings! The Glass Artists,string quartet, will cover Halloween classics and slasher themes. Don’t miss out on this night of fun! Get all the details here!
Mizery Loves Company Drag Brunch on Sunday
Join Mizery and friends on Sunday, October 19th for a day full of shows, brunch, signature drinks and did we mention shows? Limited number of tickets so get em well they’re hot! You can get yours here!
Weekend Fun at Yellow Door
Spend your weekend at Yellow Door featuring tacos, margaritas, weekend brunch (Saturday + Sunday) and $1 oysters on Sunday!
Participate in Open Streets in Mattapan on Saturday
Open Streets Boston’s 2025 series continues with the City of Boston’s next event in Mattapan – a brand new neighborhood for this year! On Saturday, October 18, we’ll be transforming Blue Hill Avenue into a pedestrian-only space that’s safe and open for everyone to explore and enjoy.
This is your opportunity to experience Mattapan like never before with a lineup of FREE activities, live entertainment, delicious food vendors, and much more. Connect with your community, make new friends, and experience this vibrant neighborhood in a completely new way. Get all the details here!
Savin Hill Halloween Parade
The 16th annual Savin Hill Little Kids Halloween parade returns to McConnell Playground this Saturday, October 18th! Children are invited to line up in their costumes starting at 3pm, with the parade kicking off at 3:15pm Sunday. Participants will trick-or-treat their way down Savin Hill Avenue and end at Savin Hill park to enjoy plenty of fall fun and activities for the whole family. The event is free and open to all. Don’t forget to bring your candy bag!
How about a little brunch?
Here our neighborhood brunch roundup! From French Toast to Omelettes, it’s all right here!
SPORTS!
Patriots vs. Saints –Sunday, October 19th at 1pm.
Bruins vs. Avalanche – Saturday, October 18th at 9pm
Bruins vs. Mammoth– Sunday, October 19th at 7pm
MLB Playoffs schedule here.
If you’re watching the game this weekend, check out our list of 10 places to catch the action in Dot, or check out 12 of our favorites in South Boston!
Check back! This list may be updated
Maureen Dahill is the editor of Caught in Southie and a lifelong resident of South Boston sometimes mistaken for a yuppie. Co-host of Caught Up, storyteller, lover of red wine and binge watching TV series. Mrs. Peter G. Follow her @MaureenCaught.
