Halloween Happenings in Weston: An Updateable List

Welcome to Weston!

Okay, things are heating up into the last two shopping weeks before Halloween. The Owl has not yet invested in the gigant-o bags of candy as this northside street does not see as many trick-or-treaters as many others. And then I have to eat ALLLLL the candy and that is very very hard. Boo hoo.

Same as last year, the Owl does not talk about the best Weston neighborhoods for Halloween (the “big” ones) because the best one is your own. It’s true. All the neighbors wish to see your little tikes and will be sad if you pass them by. If you need to know where the crazy happens, I suggest talking with classmates’ families. The top three ‘hoods are not exactly a secret…

Now, if Halloween is one of your favorite holidays, you’ll want to live it large, starting this very weekend with the Pumpkinfest. After that, it is a slippery, pumpkin-seed-filled slide into the next week full of trunk or treats and costumed events and haunted houses.

Here’s the current calendar (updated 10/20/22). Please send any updates to thewestonowl@gmail.com.

Saturday, October 22 on the Town Green, 11 am – 3 pm: Pumpkinfest, run by Weston High School students. All proceeds will benefit Camp Sunshine, a camp for young people dealing with terminal illnesses. Halloween and fall-themed activities, including pumpkin carving, food sales and a silent auction. Children can expect to participate in a variety of activities including arts and crafts, wish cards, games and face painting. You can read more here.

Friday, October 28 at an undisclosed location that you can find out through school, 4-6 pm, Trunk or Treat. This event is open to PreK-5 students from all three elementary schools and their families. Parents, please note that this is not a drop-off event and that all children need to be accompanied by an adult. Remember: nut-free candy, all.

Saturday, October 29 in downtown Weston at 10 am, the annual WCCA Halloween Parade around the Town Green and Trick-or-Treating in Weston Center. Decorate trick-or-treating bags before the parade at 10 am. Parade promptly begins at 10:30 am. Families will then be welcomed in Weston Center to trick-or-treat at local businesses. Please contact Michele Rachwalski or Stefanie Iovanna for more information.

Saturday, October 29 at Weston High School, 6-8 pm: Haunted Hospital. Walk through the hallways of Weston High School’s “Haunted Hospital” … if you dare! Cost is $13 per person or $40 per family. Pay in advance with MySchoolBucks or pay at the door with cash, check, or credit card. The Haunted Hospital is hosted by the WHS Class of 2025. Bring everyone in your family; there will be amusements and fun for every age! Check out the Haunted Hospital and graveyard; baby and child-friendly spaces with games for all ages; selfie props; spooky treats for sale; taco stand; and Chick-fil-A. Support the Class of 2025! Visit the event website.

Sunday, October 30 at First Parish Church of Weston, 11:45 am. Harvest Fest and Trunk or Treat. Community event sponsored by First Parish with pumpkin carving, trunk or treat, lots of treats and also hot apple cider and donuts. More information is at the church website here.

Monday, October 31 at the Council on Aging: Halloween Luncheon, 12-1 pm. No french-fried eyeballs here. Butternut squash soup, stuffed pork loin, mashed potatoes, roasted carrots and pie. Call the COA at 781-786-6280 to register by October 27 at 4:00 pm. Costumes are encouraged but optional.

Monday, October 31 in your neighborhood: actual HALLOWEEN! Littles start out about an hour before dark so be warned. Please please wear a reflective vest and carry a flashlight. If you are a driver, please be careful of the littles. And the bigs.

November 17-19: Extend Halloween and meet The Addams Family when Weston High School Theater Company performs this ghoulish musical comedy. See how the Addams’ kooky, upside-down world is tested when daughter Wednesday introduces her new “normal” boyfriend to the family. All performances at 7pm. Tickets can be purchased here starting October 22. Cost is $15 for adults, $10 for students and seniors (65+). Thursday night is FREE for WHS students. 

Katie Puppy as a taco. Luckily for her, she ate so many tacos it no longer fits.

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