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The Swellesley Report

Since 2005: More than you really want to know about Wellesley, Mass.

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Happy Halloween, Wellesley

October 31, 2025 by Deborah Brown

Families pre-gamed last week at the Wellesley Hills Halloween Stroll, a free annual event sponsored by the Wellesley Recreation Department and local businesses. Everybody met up at Clock Tower Park, then headed out for trick-or-treating from store to store.

Thanks to Rec for these great pics:

Wellesley Hills Halloween Stroll
There were Halloween games and fun ghoul-ore at Clock Tower Park.

Wellesley Hills Halloween Stroll

Wellesley Hills Halloween Stroll


Tonight’s the night—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.


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Calendar

Upcoming Wellesley events

Upcoming Events

Sep 7
All day

Labor Day

Sep 8
7:00 pm - 8:30 pm

Welcome to the Graveyard (Wellesley library program)

Sep 9
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Fire Extinguisher Training/Fire Safety

Sep 9
6:30 pm - 8:30 pm

The Familiar Reimagined: Artwork by Eddie Bruckner Solo Exhibition at Wellesley Free Library

Sep 10
10:00 am - 11:30 am

Wellesley Select Board office hours with Colette Aufranc

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