Passionate About Boston
and the Moms Who Live Here

Celebrating Halloween Early :: 12 Boston-Area Bashes


Pumpkins, ghosts, bats, and witches, oh my! Halloween is just around the corner! Halloween landing on a Monday this year might pose a tricky situation for the littles who are used to being tucked into bed around the same time prime trick-or-treating takes place — I know this will be the case in my house this year, with a 3-year-old and an 18-month-old who are both so excited to wear their costumes and knock on our neighbors’ doors!  

So, what to do to get in the spirit a bit earlier? Check out some of these pre-Halloween bashes taking place all around Boston before Halloween night! While immersed with fellow kiddos donning costumes at these events, no one will ever know Halloween is actually a few days later! Here are some ideas:


Halloween Parade :: Wayland Town Building, 41 Cochituate Rd., Wayland :: Monday, October 24, 3:30–4:30 p.m. :: Free

Kids in costume are invited to partake in a trick-or-treat parade and receive goodies from town building employees!

Halloween Party :: Kidville, Wellesley :: Friday, October 28, 11:20 a.m.–12:30 p.m. :: Members: $10 per child ages 1-6, free for children 0-12 months; Non-members: $15 per child ages 1-6, free for children 0-12 months

Pizza, spooktacular crafts, a Star Wars treat walk, monster mash freeze dance, and costume parade and contest all headline this Halloween party at Kidville!

Spooktacular :: Natick Common :: Saturday, October 29, noon, with parade at 2 p.m. :: Free (ages 3-K)

For the 18th year, this town-wide Halloween party will begin on the Natick Common and will feature two trick-or-treating parades for children through downtown Natick, beginning at 2 p.m.

Within Boston

Pumpkin Float :: Frog Pond, Boston Common :: Sunday, October 23, 4:30–6:30 p.m. :: Free

Bring a carved eight-inch jack-o’-lantern to this event, and watch it float on the Frog Pond in this exciting annual event! The pumpkin float is the main attraction, but there are plenty of other fun Halloween activities to partake in here, such as a haunted zombie maze, arts and crafts activities, a “bubble man,” and lots more!

PRU BOO! :: Prudential Center, Boston :: Sunday, October 30, 11 a.m.–1 p.m. :: $4 donation requested for Horizons for Homeless Children

Children are invited to trick or treat at 50 different stores throughout the Prudential Center and enjoy face painting, magic shows, activities hosted by the New England Aquarium and the Freedom Trail Foundation, and much more! As a participant in The Teal Project, PRU BOO! is an allergy-friendly event and will allow your little ones to explore this Boston landmark in a fun Halloween way. Also, following the trick-or-treating event, there will be a kids concert in the South Garden at 1:30 p.m., weather permitting!

Trick or Treat :: Brighton Business District :: Monday, October 31, 3–5 p.m. :: Free

Bring the kids along to trick or treat throughout the Brighton business district, from the Brighton Police Station to Oak Square! To complement the candy, there will be a pizza party following at the Oak Square YMCA at 5 p.m.


Trick or Treat at The Street :: The Street, Chestnut Hill :: Saturday, October 22, 1–4 p.m. :: Free

What a fun way to spend a Saturday well before Halloween! This event features trick-or-treating at many of the stores there, face painting, a photo booth and pumpkin patch, live music, and a “pooch parade” for all of our canine friends!

Halloween Trick or Treat and Boo Bash :: Legacy Place, Dedham (registration is in front of Shake Shack) :: Thursday, October 27, 4:30–6:30 p.m. :: Donations to The Greater Food Bank of Boston are required (one non-perishable food item per child is requested), and monetary donations are also accepted

Complete with a costume contest, trick-or-treating amongst the stores, balloon art, a fortune teller, and much more, this event at Legacy Place is an exciting way to kick off Halloween weekend, taking place on a Thursday.

Veterans Fair and Halloween Family Event :: Needham Town Hall, Needham :: Saturday, October 29, 1–4 p.m. :: Free

Fun for the whole family can be found at this event hosted by the West Suburban Veterans’ Services District, which features pumpkin decorating and chances to win costume prizes!

South Shore

Halloween Boo Bash :: Derby Street Shoppes, Hingham :: Saturday, October 29, 4–6 p.m. :: Free

My family and I went to this last year, and we had a blast trick-or-treating at some of the stores, listening to the live music, and enjoying the pumpkin carving and hayrides offered at this annual event — all well before bedtime.


Halloween Stroll :: Downtown Stoneham :: Saturday, October 29, 2–4 p.m. :: Free

Families can stroll around downtown Stoneham, perusing all the shops as the kids trick or treat and participate in a Halloween parade!

Fall Fest :: Assembly Square, Somerville :: Sunday, October 30, 10:30 a.m. – 2:30 p.m. :: Free

Featuring a variety of arts and crafts activities, such as making spider and ghost magnets, and a trick-or-treat event that supports The Teal Project (providing non-food treats to children with food allergies — how cool is that?!), the Fall Fest in this really fun area just outside Boston is not one to miss!

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