3.3 min readBy Published On: October 1st, 2026Categories: Features, Guide to Halloween in Southie2 Comments on Halloween Family Fun

Make sure to check back; events will be updated

Trick or Treating on Broadway

Beware of little ghosts and goblins (and their parents) roaming the streets in search for Halloween candy.  East and West Broadway will be filled with trick-or-treaters on Friday, October 30th from 4pm-6pm picking up candy from local businesses and residences.  So be warned! This event is free and is hosted by the members of the South Boston Chamber of Commerce. A special pedestrian traffic flow has been requested.  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.

Get in the Halloween Spirit

Stop by Southie Haunts this October and get in the Halloween Spirit! This home on West Fourth between D + E is decorated for Spooky SZN, and every night between 4pm-10pm there is a light show! Just press the button!  Tag us in your photos!  OPENING SOON!

Children’s Magical Halloween Castle Walk

It’s Back!  Have a hiatus, the Children’s Halloween Castle Walk will take place on Saturday, October 24th and Sunday, October 25th from 12noon-4pm. FREE ADMISSION. Storyteller. Costumes encouraged. All children must be accompanied by an adult.

Park City Pumpkinfest

Get the costumes ready! Park City Southie is hosting its annual Pumpkinfest on Sunday, October 25th from 1–4pm with pumpkin decorating, face painting, fall treats, live music, games, and plenty of family-friendly fun. There will also be a costume parade, so costumes are definitely encouraged! Get the details and tickets here.

PKL Family Halloween Event

On Saturday, October 24 from 1-4 p.m., PKL in Southie is hosting a Family Halloween event with free activities for kids and families, including pickleball, cornhole, a candy hunt for children ages 4 and under and a Halloween craft, where kids can make their own trick-or-treat bag. Throughout the event, PKL will have a dedicated pickleball court open for families to play for free from 1-4 p.m., with no reservation required. For adults, PKL will be serving Bloody Mary flights available for purchase during the event.

Trunk or Treat at the South Boston Neighborhood House

Get those costumes ready! The South Boston Neighborhood House and South Boston Family Engagement Network are hosting a Trunk or Treat celebration on Thursday, October 22nd, from 3:15pm–5:15pm at 1187 Columbia Road. Kids ages 0–8 (siblings welcome!) can enjoy games, pizza, treats, and more! The rain date is October 29th. Get the details and registration information here.

Fall-O-Ween Children’s Festival

Mayor Michelle Wu and the Boston Parks and Recreation Department will host the sixth annual Fall-o-Ween Children’s Festival at the Boston Common Frog Pond.

The Fall-o-Ween Children’s Festival is presented by the Boston Parks and Recreation Department in partnership with the Skating Club of Boston. The key sponsors are Raising Cane’s Chicken Fingers and HP Hood LLC. Additional support is provided by New England Dairy Council.

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 speed in our Monster Dash Obstacle Course or Alpine Slide and try the Jumpin’ Pumpkin or Scarecrow Slide.

A “monster mash” of activities will include music, arts and crafts, treats, and field games facilitated by Knucklebones. Visit the New England Dairy displays to enjoy both the Mobile Dairy Bar and the Mobile Dairy Experience.  Enjoy live entertainment at the Parks Department Stage with music and magic!

This family-friendly event takes place on Thursday, October 22nd from 4pm-8pm at the corner of Charles and Beacon Street.

For more information, please visit boston.gov/falloween. To stay up to date with news, events, and design and construction work in Boston parks, sign up for our email list at bit.ly/Get-Parks-Emails and follow our social channels @bostonparksdept on Twitter, Facebook, and Instagram.

2 Comments

  1. Ashley October 13, 2022 at 2:22 pm - Reply

    Is the Trick or Treat on broadway Friday the 28th or Saturday the 29th? I thought usually on Friday but wanted to be sure…the day/date don’t line up.

    • Maureen Dahill October 13, 2022 at 3:47 pm - Reply

      It’s Monday, October 31st!

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