Wellesley’s many Halloween-time traditions are gearing up, so be sure not to miss a single opportunity to dress up in costume for visits to pumpkin patches, a fun fair, the annual stroll, and more.
Here’s our roundup of Wellesley Halloween Happenings, which we’ll be updating as activities get our attention.
Don’t see your free or low-cost Halloween-time community event here? Email us at email@example.com for inclusion.
Halloween Stroll—Oct. 29
Kids and adults can get dressed up in their costumes for the annual Halloween Stroll on Saturday, October 29, 11am-1pm, starting at Clock Tower Park in Wellesley Hill, across from Green’s Hardware. Organized by the Wellesley Hill Merchants and the Wellesley Recreation Department, the free event will include trick or treating at the businesses of Wellesley Hills (remember to bring your own trick or treat bag), games, and fun for the whole family.
Halloween Spooktacular Display at 10 Falmouth Circle in Wellesley through Oct. 31
The annual neighborhood exhibit will raise funds for the Boston Rescue Mission again. Collection bins will be located by the front door and under the sign in the front yard.
Wellesley Hills Congregational Church pumpkin patch—through Oct. 31
The Wellesley Hills Congregational Church Pumpkin Patch will be open for sales through Oct. 31, 10am-6pm, on the front grounds of the 207 Washington St., church. The Pumpkin Patch will be filled with pumpkins of all shapes, sizes, and fall colors. A portion of this annual fundraiser’s proceeds will go toward reducing the cost of the church’s reforestation service trip with Led2Serve in Costa Rica. Additional proceeds will go back to the indigenous people in New Mexico who grew the pumpkins. The Pumpkin Patch volunteers hope you’ll stop by to say hello, support a great cause, and have fun picking out a couple of pumpkins.
Monday, Oct. 31—How Wellesley does Halloween
Wellesley is definitely an October 31st trick-or-treating kind of town. (Even though every year there are pockets of fret about kids getting all wound up on a school night.)
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 and fondly remember trick-or-treating as part of your misspent youth.
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.
Wellesley ghost stories
Listen to Wellesley’s Liz Sowers’ spooky “Ghosts in the Burbs” podcast.
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Events that have happened:
Halloween House Decorating Contest nomination deadline—Oct. 26
Wellesley Recreation Department invites you to nominate someone from your neighborhood, or your own haunted house, for the 8th annual Howlin’ Haunted Halloween House Decorating Contest.
To nominate a house:
- Send a picture to firstname.lastname@example.org
- Don’t forget to include the address of the decorated house.
- If the house has lights, please take a day and night picture.
Nominations close Wed., Oct. 26, 10am.
Eyes on Owls—Oct. 27
Join Marcia and Mark Wilson and SIX live owls for an exciting evening. Learn owl field markings and skills you can use to find owls in the wild. Participate in a hooting lesson, and see owls up close and personal. For all ages.
Halloween costumes and masks are optional. Come one and all—it will be a hoooot!
This is a Wellesley Conservation Land Trust Educational Series event, co-sponsored with the Wellesley Free Library
DATE: Thursday, October 27, 2022 – 6:30pm
LOCATION: Wellesley Free Library, 530 Washington St.
Poets Neighborhood Haunted House—Oct. 22
Schofield 5th graders, along with their parents and siblings, are rolling up their sleeves to help build and set up the Poets Neighborhood Haunted House that will take place on Saturday, October 22, 5:30-8:30pm, at 67 Whittier Road.
Families will also work the fundraising event, so those clowns you see during the tour of the “Creepy Carnival” themed event just might be your neighbors getting in touch with their scary side.
The long-standing neighborhood tradition has been hosted by the same community-minded family since 2012 (with a couple off years due to the pandemic).
DATE: Saturday, October 22
LOCATION: 67 Whittier Road
COST: Optional donations. Funds will benefit the Schofield 5th grade class for things things like class t-shirts, yearbooks (one for each student), a class gift, a staff appreciation luncheon in the spring, an end-of-the-year class field trip and the Moving Up Ceremony.
Halloween fun at Linden Square Pumpkin Patch—Oct. 22
Stop by the Linden Square Pumpkin Patch for Halloween fun, Saturday, Oct. 22, 10am-noon. There will be FREE pumpkin decorating, trick-or-treating (Bach to Rock, Momentum Dance, Kenzie & Hope, Magic Beans, StretchLab), and a visit from Peppa Pig for kids ages 3-12. Costumes are optional. A $5 Starbucks gift card will be given to the 10 best costumes—only kids are eligible.
Stop by anytime before Halloween and snap a photo in front of the Pumpkin Patch and post on social with #LindenPumpkinPatch for a chance to win a $50 Linden gift card to the store or restaurant of your choice. One random winner will be selected by November 1. Events made possible through a partnership with Wellesley Recreation Department and Roche Bros.
Bates Elementary School Pumpkin Fair—Oct. 15
The Bates Pumpkin Fair will take place on Saturday, October 15, noon-4pm on school grounds at 116 Elmwood Road.
Come in costume for an afternoon of games, prizes, a haunted house, sweet treats, pumpkins, face painting, food for purchase, bouncy houses, live entertainment, and more at the fundraising event.