Together With

Good morning Oakville. Happy Wednesday!

Here is what to expect in today’s issue:

  • 🎭 The Oakville Players present “A Few Good Men”, The Oakville Remembrance Trail Run supports Wounded Warriors Canada, and applications open for HDSB specialized high school programs

  • 🎥 Brooke Shields shares her visit to Oakville’s 5 Drive-In, local mom innovates the hockey trading card pastime

  • 🗓️ Some exciting events to keep you busy!

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

~ Nick

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The Oakville Players Present ‘A Few Good Men’ 🎭

The Oakville Players

One of the most famously dramatic courtroom confrontations in playwriting history will soon come to life at the Queen Elizabeth Black Box Theatre, where the Oakville Players will stage 10  performances of ‘A Few Good Men’ between Thursday, November 5th and Sunday, November 15th. 

This tale of murder, conspiracy, and a high-stakes court-martial first dazzled audiences on Broadway before it was turned into a hit 1992 movie. In the Oakville Players’ production, Chris Reid will take on the role of Colonel Jessep (played so memorably by Jack Nicholson on film) while Andy Ingram will spar with him in the courtroom as Daniel Kaffee (the Tom Cruise part). 

Tickets are on sale now, and a dinner + show package is also available for the Saturday, November 7th evening performance. An entertaining night out—if you can handle the truth!

Remembrance Trail Run Happening Saturday  🏃

Last year, Wounded Warriors Canada held the inaugural Oakville Remembrance Trail Run and raised over $20,000 to support the mental health of veterans, first responders, and their families. This Saturday, November 7th, they’re hoping to build more momentum off that success when the event returns to Lion’s Valley for the second year.

Starting at 10am, runners can choose between the 11km and 5km trail routes. The 5km trail is a new addition this year, to make the event more inclusive for participants of all abilities. Also new this year is the Marc Pinizzotto Cup, the trophy that will be given to the highest fundraising team, named in memory of the Oakville Constable who lost his life in the line of duty earlier this year.  

Last year’s run was an impactful way for the community to actively support those who have served, and now with the run returning for its second year that support is becoming an important Oakville tradition.

Applications Open For Specialized Programs At HDSB Schools ✏️

High achieving high school students have more opportunities than ever to pursue their interests within the Halton District School Board. The school board will offer four different specialized programs for the 2027/2028 academic year, and applications for these programs are now open.

Advanced Placement (AP) classes are designed to challenge and prepare students for university-level learning, while the International Baccalaureate (IBDP) program is known for being academically rigorous and producing excellence, and HDSB’s I-STEM is a four year opportunity for students to study in a hands-on, technology-focused way. In 2027 the board will launch the Academy For Athletic Performance and Excellence (APEX) at the yet-to-be-named new school at 4020 Sixth Line, intended to attract high level competitive student-athletes.     

Applications are available online and will be accepted until 11:59pm on November 30th. Good luck to everyone setting out on their specialized educational journey!

📰 More News

Hollywood Star Drops By The 5 Drive-In 🎥

@Brookeshields on Instagram

Stars have been spotted at the 5 Drive-In movie theatre plenty of times before, but typically they’re on the screens and not in one of the cars! So it was delightfully unexpected when storied actress Brooke Shields documented her recent trip to the nostalgic Oakville spot for her social media feeds. 

Shields has been in the area filming the second season of her crime tv series You’re Killing Me, and between shoots she’s made the most of her Ontario time, exploring everywhere from Niagara Falls to Unionville. She stopped by Oakville’s 5 Drive-In to take in the much-talked-about You Can See Everything with her Canadian co-star Amalia Williamson, and the two definitely seemed to enjoy the old-fashioned drive-in experience, marvelling over the way the sound played through the car radio. 

The theatre has long been one of Oakville’s not-so-hidden gems, featured this past summer in several viral TikToks, and now that a bonafide celebrity has stopped by the drive-in seems even more iconic!

Oakville Mom’s New Venture Inspired By Son’s Love Of Hockey Cards 💻 

Anyone who collects the Tim Hortons NHL trading cards knows that the hobby can be about as frustrating as it is fun, between all the pesky doubles that stack up and the rare high value cards that remain elusive even after many packs are purchased. But Oakville’s Michelle Oryschak has designed a new solution for these problems. 

Inspired by her son’s childhood love of collecting the cards, a pastime the whole Oryschak family eventually became invested in as well, Michelle created Binder Bench, a platform intended to make trading cards and completing collections easier for children. 

A season-long membership to Binder Bench is $14.99 but beyond that there is no cost for trading cards within the community. There are no expensive sales or exorbitant auctions, just friendly exchanges between kids who collect for the simple love of the game!

🏒 U17 World Challenge
Tue-Sat 11/3-11/7
Sixteen Mile Sports Complex

🌹 Royal Canadian Legion Poppy Sales
Tue-Tue 11/3-11/10
Oakville Place

🎄 Holiday Market Sip & Shop
Wed 11/4 @ 6PM-9PM
Marine Tavern

🎭 A Few Good Men
Thu-Sun 11/5-11/15
Queen Elizabeth Park Community and Cultural Centre (Black Box)

📚 BookTalk, Live! 2026
Thu 11/5 @ 6PM-9PM
Queen Elizabeth Park Community and Cultural Centre in the Rehearsal Hall

🎤 In Conversation with Peter Mansbridge & Mark Bulgutch
Thu 11/5 @ 7PM-9PM
Oakville Centre for the Performing Arts

🪔 Diwali Craft Workshop
Fri 11/6 @ 3PM-4:30PM
The Women's Centre of Halton

🏃 Oakville Remembrance Trail Run
Sat 11/7 @ 10AM
Upper Middle Park

🐰 Rabbit Adoptathon
Sat-Sun 11/7-11/8 @ 10AM
Humane Society of Oakville, Milton & Halton

🚪 St. Paul's United Church Open House
Sat 11/7 @ 10AM-2PM
St. Paul's United Church

✍️ Calligraphy Workshop
Sat 11/7 @ 11AM-2PM
350 Lakeshore Rd E

🎹 Olga Popova — Piano Concert of Original Music
Sun 11/8 @ 3PM-6PM
St. Volodymyr Event Centre

🎻 Vivaldi and Company
Sun 11/8 @ 7:30PM-9:30PM
Oakville Centre for the Performing Arts

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

Wednesday, November 4
🌦️ Chance of showers
High: 21°C | Low: 13°C

Thursday, November 5
🌦️ Chance of showers
High: 17°C | Low: 7°C

Friday, November 6
🌦️ Chance of showers
High: 14°C | Low: 9°C

WEDNESDAY
7PM · Figaro Coffee House · The Dyanne Dumas Trio
7PM · The Gingerman · Open Mic with Pop Machine

THURSDAY
1PM · Moonshine Cafe · Open Ukulele Session
8PM · Moonshine Cafe · Dead Root Revival

FRIDAY
8PM · Moonshine Cafe · Cheryl Lescom & The Tucson Choirboys
8PM · The Gingerman · Kim Foo Band
8PM · BLK Swan · Rocket 88
8PM · Lionheart Pub · Anthony Tullo

SATURDAY
2:30PM · Moonshine Cafe · Mike Branton & Friends
8PM · Moonshine Cafe · Cherry Garcia
8PM · Lionheart Pub · Blindfold Test Band
8PM · Easy on Fourth · Live Music Saturdays
8PM · The Gingerman · Descendants Of Dunn
8:30PM · The Oakville Pump & Patio · Otis Wonder and The Hustle

SUNDAY
2:30PM · Moonshine Cafe · Bob Wiseman & Doug Paisley
2:30PM · Bronte Legion · Live Music on the Patio

  • Wednesday Night at BLK Swan Kitchen Hub

  • Wednesday at Kelsey's Burloak

  • Wednesday at Lionheart British Pub

  • Thursday at The Bronte Legion, 79 Jones St

Thanks for reading the Oakville Digest today. If you know someone who enjoys an unexpected celebrity sighting, please share this with them!

~ Nick

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