Fall is one of our family’s most favorite times in the city.  The once strongly humid and sticky air is now crisp and cool, making it ideal weather for long park playdates or nature excursions.

Strolling through our South End neighborhood, we love collecting colorful leaves, cute little acorns, and bumpy sticks to paint back at home.  It feels a tad like bits and pieces of the calmer suburban lifestyle sprinkled throughout the city.

Last week we stopped by the Copley Square Farmers Market (every Tuesday and Friday, 11am-6pm) to pick up tiny pumpkins to decorate so we could welcome fall.  Though my favorite things about the season may be vests and riding boots, pumpkin spice lattes and cider, we know October means only one thing to our littles—Halloween!  And living in the South End, we are able to attend some wonderful local upcoming events! 

Little Lovage Club’s Halloween Jam with Vanessa Trien

778 Tremont Street

Boston, MA  02118

Friday, October 28th

3:30-4:10, 4:20-5pm

Little Lovage Club offers the coziest spot to let your littles get their Halloween on!  Rock out to jams with Vanessa Trien and scoop and nibble from their candy buffet, while wearing your spookiest, silliest, Halloween best.  $12 per child.  Call 617-651-2620 to register now for your spot!

*Insider tip: There are only a few indoor Halloween bashes, and this is one of them!  Rain or shine, this is a particularly great place for new moms of teeny littles to meet.


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 29th

12-3 pm

This event is truly packed with fun for all ages!  Pumpkin decorating, a dog costume contest, Halloween stories read by Anne Smart of the South End Library, and a haunted graveyard tour of the South End Buriel Ground (and more!) means every person in your crew will find something they love to do.

*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.

Prudential Center’s “Pru Boo”

The Shops at the Prudential Center

800 Boylston Street

Boston, MA  02199

Sunday, October 30th

11 am-1 pm: Trick or Treating

1:30 pm:  Kids’ Concert

A yearly staple for local families, the Prudential Center’s “Pru Boo” is always a hit.  Purchase a trick-or-treating bag as early as October 1st at the Customer Service desk, or arrive early the day of the event (beginning at 9 am) to secure your spot.  Bags sell for a $4 donation, this year benefitting their non-profit partner Horizons for Homeless Children.  Trick-or-treat with your littles around the mall, stopping at participating stores, before heading over for face painting, a magic show, and kids’ concert in the South Garden.

*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.

Tadpole’s Chandler Street Block Party

58 Clarendon Street

Boston, MA  02116

Sunday, October 30th

2-4 pm

Year to year, Tadpole’s Halloween bash keeps us coming back for more.  The bouncy house very well may be a fan favorite, and the goodies provided by local eateries tide little tummies over while kids search for treasures in hay, have glitter tattoos applied, or complete a fun craft.

*Insider tip: Have a child old enough to join in on the bouncy house fun?  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 at Ringgold Park

81 Montgomery Street

Boston, MA  02118

Monday, October 31st: Halloween Day

5 pm

If you live close to the South End, you’ve probably heard about Union Park’s famous Halloween decor.  Just down the street, Ringgold Park is the perfect spot to hit before heading out for some trick-or-treating fun.  Always packed, you can grab a bite to eat while letting the littles play in one of the two enclosed play areas.

*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

Monday, October 31st: Halloween Day

5-6 pm

Dance to classic Halloween tunes, strike a pose at the photo booth, and snack on yummy treats and cider at Titus Sparrow’s annual event.  The park has a big open space that is perfect for older children to run in, and separate large and small climbing structures for preschoolers and toddlers.  Complete with baby swings for infants, this park is the perfect spot to celebrate Halloween with a bigger group, and family and friends who have children of mixed ages.

*Insider tip: Have a group of friends with babies who won’t be trick-or-treating?  Make a reservation for dinner at Five Horses just down to the street, to cap off the evening with some apps and beer!

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