The South End in fall—crisp air, crunchy fallen leaves on brick sidewalks, and pumpkins lining brownstone stoops—we know these sure signs of autumn in our neighborhood. And once we start seeing the folks on Union Park putting up their well-known décor, we know one thing for sure: it must be getting close to Halloween!

Whether you have friends with littles in town, or have a baby or toddler yourself, there is so much to take advantage of in the area.


Prudential Center’s “Pru Boo”
800 Boylston Street – Boston, MA 02199
Sunday, October 25
11 am-1 pm: Trick or Treating
1:30 pm: Concert

Bring your littles to trick-or-treat at fifty participating shops and restaurants in the Pru—stopping along the way for face painting, magic shows, and other fun activities. A $4 donation goes straight to their non-profit partner Room to Grow, an amazing local organization whose mission it is to help babies born into poverty. Stop by the service desk as early as the first of October, to give your donation and receive your trick-or-treating bag, or get there early the day of the event to secure your spot! Weather permitting, Vanessa Trien will perform a kids concert in the South Garden. If it’s a rainy day, follow the music to the Belvidere Pavilion.

*Insider tip: It get very busy, so if you can forgo the stroller, you’ll save yourself a bit of hassle with navigating around the crowds.

Little Lovage Club’s Monster Mash with Jeff Jam
778 Tremont Street – Boston, MA 02118
Friday, October 30
3:30-5 pm

Do the mash—the monster mash!, with Jeff Jam, of course! Tucked away in a brightly naturally lit space, Little Lovage Club will keep you and the kids cozy warm while you have some spooky, silly fun.

Reserve your space here – only 5 spots left!

*Inside tip: Interested in attending events that overlap? Sign up for the earlier session here to make it in time for other South End Halloween-themed fun.

Tadpole’s Chandler Street Block Party
58 Clarendon Street – Boston, MA 02116
Friday, October 30
4:30-6:30 pm

This yearly neighborhood event is one not to be missed. Mini cupcakes and brownies from the Buttery await hungry kiddos just arriving after a long snooze, and the line for the bouncy house always fills up fast. Face painting, treasures hidden in hay, and crafts keep children of all ages busy, and tire them out for the evening ahead.

*Inside tip: If other years are any indicator, the bouncy house very well may be the hit of the evening. Have a child old enough to join in? Arrive to the party when it begins and let them get their jumping out before moving on to other, not as busy activities offered.


Halloween Festival in Blackstone Square
Blackstone Square is located between West Brookline Street, Shawmut Avenue, West Newton Street and Washington Street
Boston, MA 02118
Saturday, October 31
12-4 pm

With enough space to accommodate the entire South End and then some, this Halloween event runs the longest and has the best potential for hosting big groups. Offering traditional face painting and Halloween stories, they also have some extras like food trucks and a costume contest for dogs!

*Insider tip: Going with a crew? Make an early reservation around the corner at Stella and ask to sit in the quieter, smaller side room by the windows. You’ll be able to park your strollers outside right in front and keep an eye on them from the warm cozy restaurant while chowing down.


Ringgold Halloween at Ringgold Park
Ringgold Street – Boston, MA 02118
Saturday, October 31
4:30-6 pm

Every year right before heading out to trick-or-treat down the famous décor of Union Park, Ringgold Park hosts an hour or two of crazy busy fun! Often filled with local pizza, large tables await with potluck offerings to munch on while the little ones can choose to play either in the big or smaller kid side of the playground.

*Insider tip: Planning on trick-or-treating straight from the fun? Attempt to nix bringing the stroller along. The sidewalks of Union Park are crammed with excited children and teens, and toting along a toddler plus the stroller makes for double duty. An Ergo, even worn on your back, will save you from tired arms from carrying a heavy, tired kid!

Titus Sparrow Park’s Pre Trick or Treat Party
200 W Newton Street – Boston, MA 02118
Saturday, October 31
5-6 pm

Baby swings for the super littles and climbing structures for the bigger kids, this park offers a traditional playground in addition to the large open grass area where children and adults can jam to Halloween tunes, snack on Upper Crust pizza, and sip on cider.

*Insider tip: Looking for the perfect party to attend with your new parents’ group? This one has the space needed for larger parties and group picture taking. Make a reservation far out at Five Horses just down to the street, to cap off the evening with some apps and beer!