Wellesley Halloween happenings—2025 edition
Halloween Happenings is sponsored by Wellesley Hills Church Pumpkin Patch
Wellesley’s many Halloween-time traditions are gearing up (already!), so be sure not to miss a single opportunity to dress up in costume, visit pumpkin patches, enjoy a fall festival, and more.
In Wellesley, kids go treat or treating on… Halloween, which is on Friday, Oct. 31. So nice to have a year when we don’t have to send them back to school the very next day, hungover on sugar.
Here’s our roundup of Wellesley Halloween Happenings, which we’ll be updating as activities get our attention.
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Wellesley Hills Congregational Church Pumpkin Patch
DATES: through Oct. 31
LOCATION: 207 Washington St.
Visually fabulous, and sales support a good cause.
Halloween Stroll, Oct. 25
DATE: Saturday, Oct. 25
TIME: 11am-1pm
DESCRIPTION: This FREE event will begin at Clock Tower Park, across from Green’s Hardware, in Wellesley Hills. Beginning at 11am, children will be encouraged to trick or treat at the businesses of Wellesley Hills. Please remember to bring your own trick or treat bag! Games and fun ghoul-ore.
AGES: 0-8yr.
House Decorating Contest, nomination deadline, Oct. 25
WHAT: Howlin’ Haunted Halloween House Decorating Contest
TO DO: Take a picture of the nominated house along with the address and email it to recreation@wellesleyma.gov
DEADLINE: Nominations must be received by 10am on Friday, October 25
CATEGORIES: Scariest & Judges Choice. Awards delivered by the Boo Crew
SPONSORED BY: Wellesley Rec.
Halloween at Fay School, Southborough
DATE: Saturday, Oct. 25
TIME: 10am-1pm
LOCATION: Fay School’s quad
DESCRIPTION: Storytime – 10:15am; Children’s Costume Parade – 10:45am; Halloween Concert featuring Lenka Zbruz – 11:15am
COST: event is free; purchases from the ice cream truck will require cash or credit card
Pumpkin Decoupage Craft and Movie
DATE: Tuesday, Oct. 28
TIME: 6pm-8pm
LOCATION: Wellesley Free Library
DESCRIPTION: Enjoy some spooky pumpkin decoupage while watching Practical Magic (1998). Decoupage is the art of decorating an object by gluing colored paper cutouts onto it in combination with Mod Podge glue. Materials will be a combination of colorful Halloween paper and napkins to decorate mini pumpkins.
Practical Magic (1998) takes place in a small, contemporary New England town, for two sisters from a family of witches, falling in love is the trickiest spell of all. They struggle to use their gift for magically guiding fate to overcome their family curse: The men they fall in love with are doomed to an untimely death! Based on the novel by Alice Hoffman. Practical Magic (1998) is rated PG-13.
This program is for ages 13+ and adults.
Halloween is Friday, Oct. 31
In Wellesley, kids go treat or treating on… Halloween, which is on Friday, Oct. 31. Nice to have a year when we don’t have to send them back to school the very next day, sleep deprived and hungover on sugar.
How Wellesley does Halloween
Wellesley is definitely an October 31st trick-or-treating kind of town. Generally speaking, the littlest ones go out in their own neighborhoods at about 6pm.The older kids head out a little bit later, around 6:30. We heckle kids who show up either without a costume or wearing a Patriots jersey and claiming, “I’m dressed up like a football player.” Seriously, big kids, if you’re too cool to put together a real costume, it’s time to let it go. Most residents at 8pm close their doors, blow out the candles in their jack o’ lanterns, and turn off their front porch lights to signal that their house is done with Halloween.This can vary from neighborhood to neighborhood, but not by much. As far as the candy goes, certain houses have a reputation for handing out full-sized bars, and the rabid following that goes with such generosity. We’re not going to spill those sweet secrets here. You’ll have to get out there and find the best pickings for yourself.
Our biggest fear…
Here at The Swellesley Report, we’re terrified that you haven’t signed up for all our things. Allow us to treat you to “more than you really need to know about Wellesley, Massachusetts” in the following non-scary ways:
These events have passed:
Halloween-time event at Linden Square, Oct. 18
DATE: October 18
TIME: 1pm-3pm
LOCATION: Linden Square
COST: FREE Halloween fun for kids ages 3-12!
DESCRIPTION: Celebrate the season with pumpkin decorating in The Courtyard, Trick-or-Treating at participating Linden Square shops and restaurants, and delicious samples from Oath Pizza and Playa Bowls.
Kids can also climb aboard a real fire truck, courtesy of the Wellesley Fire Department, enjoy festive tunes, explore an Instrumental Petting Zoo with Bach to Rock, and make crafts with the Wellesley Lions Club.
Costumes encouraged—come join the fun!
Acatober—Oct. 17 & 18
You won’t want to miss Acatober, two evenings of singing that will feature all Wellesley High School choirs and a cappella groups, along with special guest groups (TBA). Tickets go fast every year for this incredibly popular concert that always reminds us how lucky we are to have such an amazing public school choral program at Wellesley High.
DATES: Friday, Oct. 17 & Saturday, Oct. 18
TIME: 7pm-9pm, both nights
LOCATION: Katherine L Babson, Jr Auditorium at Wellesley High School
TICKET SALES: Available now
Linden Square Giveaway—deadline Oct. 9
DATE: Saturday, Oct. 4
TIME: noon-4pm
LOCATION: Bates Elementary School, 116 Elmwood Rd.
DESCRIPTION: The Pumpkin Fair returns with exciting games, thrilling rides, balloon artists, tasty treats, magicians, dancing, and more! The Pumpkin Fair is a fun day for kids and families, a beloved tradition, and a vital fundraiser for the Bates PTO.
West Suburban YMCA’s Annual Fall Festival
DATE: Saturday, Oct. 4
TIME: 11am-1pm
LOCATION: 276 Church Street, Newton
DESCRIPTION: Get ready for an afternoon full of autumn excitement. From pumpkin decorating and games to music, snacks, and surprises, there’s something for everyone to enjoy. Come in costume and celebrate the season. This beloved community event is free and open to the public.