Perfect Day in Whitby, Ontario: Chastity

An afternoon out in Brandon Williams’ hometown, whose lore inspired his latest pop-punk collection I Built This Prison Myself.
Perfect Day

Perfect Day in Whitby, Ontario: Chastity

An afternoon out in Brandon Williams’ hometown, whose lore inspired his latest pop-punk collection I Built This Prison Myself.

Words: FLOOD Staff

Photo: Alex Clarke

November 09, 2026

It’s been over a decade since Brandon Williams launched his band Chastity, and even after label deals with Captured Tracks, Deathwish Inc., and Dine Alone Records and the global audience they’ve helped him develop across five albums and countless tours, Whitby, Ontario is still where he calls home. It’s the town Williams grew up in, and rather than gravitating toward nearby Toronto or any other hubs of punk or hardcore, he’s instead fostered a burgeoning DIY community within the modest confines of the town on Lake Ontario.

In fact, Whitby is at the center of Williams’ latest record, I Built This Prison Myself, which taps into the local lore of a psych ward that burned down in the ’70s at the hands of a teen patient. Metaphors abound as Chastity’s patented fusion of soaring pop-punk vocals and deceptively heavy guitars soundtrack reflective ballads of youthful angst and fiery ruminations on taking matters into one’s own hands.

With the record dropping this week via Deathwish and Dine Alone, Williams took us along on a scenic trip through Whitby, with stops at some favorite vintage shops, decaf-friendly coffee spots, strip-mall food courts (what the fuck is up, Denny’s?), and more. Find his words and pictures below, and pre-order I Built This Prison Myself here.

This is the neighborhood I grew up in. I’m on a parking garage taking this photo—this feels like the top of the world to me, a start to a perfect day. 

I don’t drink caffeine, but I eat pastries. I believe M & L Motors is great at both—today I know the pastries part. 

Jug City: hilarious name for everybody to enjoy. The veil is thin in this plaza—heaven is near and I can feel it here.

Vintage 905 is the only place I get clothes from anymore. This is the closest thing in my life to a coffee shop—knowing what I like in my coffee without me saying. Love ’em. 

Starr Burger for lunch. My brother and I have merch from this place.

Station Gallery is free, and the curator there, Charlotte, has great taste, so there’s always cool stuff. She’s in today.

The food court and Denny’s are the only non-bars open late. I’ve finished a lot of great days at the food court.