Get Ready for a Spooktacular Family Fun in the Neighborhood: Trick-or-Treating on Broadway, Castle Island’s Magical Castle + Ollie Trunk or Treat

Things are getting a little spooky in the neighborhood with the return of two favorite family-friendly events!
Trick or Treating on Broadway
Beware of little ghosts and goblins (and their parents) roaming the streets in search of Halloween candy. East and West Broadway will be filled with trick-or-treaters, picking up candy from local businesses and residences on Friday, October 31st, from 4 pm to 6 pm.
Participating establishments will be clearly marked with orange and black posters inviting the children to stop by for a treat.
For the safety and enjoyment of all participants, we are asking that Trick-or-Treaters walk in the same direction. If you are starting on West Broadway going toward East Broadway, walk on the odd-numbered (southern) side of the street. If you are starting on East Broadway heading to West Broadway, walk on the even-numbered (northern) side of the street.
Ollie’s Trunk or Treat Event
Castle Island Magical Castle
The Castle Island Magical Castle will take place on Saturday, October 25th, and Sunday, October 26th, from 12:00 p.m. to 4:00 p.m. FREE ADMISSION! There will be storytelling, costumes are encouraged and an adult must accompany children!

Maureen Dahill is the founder of Caught in Media. Once a longtime wardrobe and prop stylist for brands such as Rue La La, TJ Max & Hasbro, she is a devoted lover of vintage clothing, Martini Mondays, Castle Island, AND a 4th generation South Boston native. Mother of three, married to Peter G.


Don’t forget the Ollie is having our annual ‘trunk or treat’ event at the Preschool Parking Lot on Thursday, October 30th from 3:30–5:30