Good morning Oakville. Happy Friday!

🦃 Quick heads up: we’re taking the long weekend off, so there’s no newsletter this Monday. Enjoy your Thanksgiving (and the leftovers), and we’ll see you Wednesday!

Here is what to expect in today’s issue:

  • 🎬 Film crews spotted around Oakville, Mayoral candidate debate scheduled, & Haunted Happenings at the Oakville Museum

  • 🍝 Introducing our new “Local Eats” feature, with a spotlight on Sotto Sotto and Part One of our 2026 Oakville Fall Treat Round Up

  • 🗓️ Some exciting events to keep you busy!

Thanks for being part of our growing community, let’s dive in!

~ Nick

Film Crews Spotted Around Oakville 🎬

The Oakville Digest

If you’ve driven past Oakville Place recently, you’ve probably seen the cluster of trailers and a large tent that have been set up over an expansive section of the mall’s upper parking lot. For once, this hub isn’t for any kind of fair or festival. Instead, it’s a production facility for the Disney+ series The Testaments, which is currently filming parts of its second season here in Oakville. 

The dystopian series is a spin-off of The Handmaid’s Tale, and is also based on another acclaimed Margaret Atwood novel. Oakville’s Chelster Hall already served as a production location during the show’s first season, and now crews have been spotted around Tannery Park and other waterfront and heritage sites, so we’ll see if Oakville plays a leading or supporting role in season two!

Mayoral Debate Set For October 18th 🗣️

All five of Oakville’s mayoral candidates have been invited to participate in a debate hosted by the Oakville and District Labour Council, Unifor Local 707, and Advancement of Women Halton. The debate is set to take place on Sunday, October 18th from 3-5pm at the Unifor 707 Union Hall. 

Though late in the election cycle, coming only eight days before Election Day, organizers hope the debate will be an opportunity for the candidates to share their positions on the issues that matter most to working people. Democracy is a dialogue between voters and their representatives, and it works best when everyone participates!

Haunted Happenings At The Oakville Museum 👻

The Oakville Museum at Erchless Estate will be Oakville’s official headquarters for all things Halloween this year, with a full slate of spooky tours and events happening throughout October, all designed for visitors to discover the haunted side of history. 

Daily Haunted Happenings tours will be held Tuesdays through Sundays, where visitors will be guided through both the museum and the evolution of Halloween traditions. A Candlelight variation will be held on select nights for those seeking a more ghostly flair, and then on Saturday, October 24th, the museum will become a bonafide boo-nanaza of activity, with a ticketed family-friendly event full of crafts, games, snacks, and surprises.  

If you’re looking for tricks, treats, and trips back into the past, this possibly haunted house is definitely the place to be!        

Restaurant Spotlight: Sotto Sotto 🍝

The Oakville Digest

Set just a couple of blocks away from the buzz of Lakeshore Road and tucked into a more secluded corner of Downtown Oakville, Sotto Sotto is an upscale, atmospheric restaurant that takes great pride in its authentic approach to Italian cuisine. While its Toronto location has become legendary during its 30 years of operation, even getting name dropped in several Drake songs, the Oakville Sotto Sotto opened only four years ago and has been quietly earning loyalty with local diners ever since. 

At night, the small intimate dining room flickers with candlelight, and diners huddle around bottles of wine and heaping plates of pasta. Executive Chef Massimo Renzi hails from Rome, so the menu features Roman specialties like cacio pepe and carbonara, along with a well-considered selection of other Italian fare, including desserts worthy of leaving room for, like the pistachio gelato and the tiramisu. 

Prices are indeed on the higher end, though considerably less than a plane ticket to Rome, so if you’re ever searching for an authentic Italian dining experience close to home, Sotto Sotto is thankfully only a few Spanish Steps away. 

2026 Oakville Fall Treat Round Up: Part One! 🥧

The Oakville Digest

When autumn arrives, the days get shorter and the temperature starts to drop, but thankfully and perhaps to compensate, Oakville’s bakeries are pulling even more delicious treats out of their ovens. To celebrate this delicious abundance, we’re trying all of the apple-flavoured and pumpkin-spiced offerings we can find. 

This week’s highlights include the new pumpkin macaron from Nadege, the PSL cupcake recently crowned Oakville’s fave from Kelly’s Bake Shoppe, and an artistically painted autumn leaf sugar cookie and apple crumble tart from Black Forest Pastry Shop, who recently announced this will be their last fall in Oakville. 

Whether you’re looking to add something to your Thanksgiving table or to simply enjoy on an autumn afternoon of your own, when it comes to desserts, Oakville has a full harvest. And we’re just getting started! 

Friday, October 9
🌤️ Mainly sunny
High: 19°C | Low: 6°C

Saturday, October 10
⛅ A mix of sun and cloud
High: 20°C | Low: 11°C

Sunday, October 11
🌦️ Chance of showers
High: 20°C | Low: 12°C

Oakville Digest is 100% free to read, independently owned, and locally operated (written by me).

Your contributions go directly towards keeping this newsletter going so we can have more fun and build more community.

Thank you for your support!
~ Nick

🍪 Halloween Cookie Decorating Workshop
Fri 10/9 @ 6:30PM-8:30PM
Touchdown Coworking Space

🚶 Oakville Underground Railroad Walking Tour
Sat-Sun 10/10-10/11 @ 1PM
Oakville Museum

💘 Oakville Speed Dating
Sat 10/10 @ 2:01PM-4:01PM
Swiss Chalet Oakville

😂 All You Can Laugh!
Sun 10/11 @ 8PM
Moonshine Cafe

👻 Ghost Walks
Tue 10/13 @ 6:30PM
Oakville Historical Society

🎭 First Drafts: The Chrysalids & Trembler’s Waltz
Tue-Sat 10/13-10/17
Studio Theatre - Sheridan Trafalgar Campus

🎨 Aideen Barry Artist Talk
Wed 10/14 @ 1PM-2PM
Sheridan College Trafalgar Campus

🎤 Neil Diamond Concert Celebration
Wed 10/14 @ 7:30PM-9:30PM
Oakville Centre for the Performing Arts

🎸 LIVE MUSIC

FRIDAY

Moonshine Cafe | Shrimp Daddy | 8PM
Lionheart British Pub | Anthony Tullo | 8PM
BLK Swan Kitchen Hub | The Shakes | 8PM
The Gingerman Social Eatery | Hot Buttered Soul | 8PM

SATURDAY

Moonshine Cafe | Mike Branton & Friends | 2:30PM
Easy on Fourth | Live Music Saturdays | 8PM
Lionheart British Pub | Martin Fransisco | 8PM
Moonshine Cafe | Grant Lyle & James Anthony | 8PM
The Gingerman Social Eatery | Night Owls | 8PM
The Oakville Pump | Rock Express Band | 8:30PM

SUNDAY

The Bronte Legion, 79 Jones St | Live Music on The Legion Patio | 2:30PM

Thanks for reading the Oakville Digest today. If you know anyone who’s been curious about the trucks around Oakville Place, please share this with them!

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NICK POLLOCK
Founder / The Oakville Digest
[email protected]