Good morning Oakville. Happy Wednesday!

Here is what to expect in today’s issue:

  • 🎅 Santa Parade Returns & Readers’ Choice Revealed

  • 🎁 $250K for Local Support & Oakville’s NHL Debut

  • 📅 Some exciting events coming up!

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

~ Nick

🔑 On The Market

Check out this listing from The Benson Crew on Goodyear Road:

Can you guess the price?
Click here for a reveal.

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🎅 Santa Claus Parade Returns Nov. 15

Source: oakville.ca

Downtown Oakville will come alive with winter cheer as the 77th annual Santa Claus Parade kicks off Saturday, November 15 at 9am. This year’s theme, Snow Much Fun, highlights snowy pastimes like sledding, skating, and snowball fights. Expect lively marching bands, community floats, and plenty of festive spirit. Attendees are encouraged to wear their holiday best and soak up the seasonal magic.

Kids can enter a colouring contest for a chance to ride with Mrs. Claus as Honorary Grand Marshal, using artwork by muralist Yasaman Mehrsa. Free shuttles will run from Oakville GO to Trafalgar Park Community Centre every 5-10 minutes from 8-11:30am. Temporary road closures will be in effect, with full details on the Town’s website.

🏆 2025 Readers’ Choice Finalists Revealed

The Oakville Beaver has announced the finalists for its 2025 Readers’ Choice Awards, spotlighting top-rated local businesses as chosen by the community. Categories span everything from best restaurant and pet groomer to favourite summer event and fundraiser of the year.

New this year is a nod to neighbourhood charm with a category for best Christmas lights display. The full list of winners and finalists is available on the Oakville Beaver’s website.

💰 $250K Boost for United Way Halton

United Way Halton and Hamilton has received a $250,000 grand prize from OLG’s Wintario50 Community Contest, one of only two top awards given across the province. The initiative celebrated OLG’s 50 years of community support by distributing over $1 million to all 26 United Way regions in Ontario, with nominations coming from players who bought Wintario50 tickets.

CEO Brad Park thanked the community for helping secure the win, saying the funds will go toward strengthening essential social services across Halton and Hamilton. A well-earned boost for vital local programs.

🏒 Oakville’s Curtis Douglas Makes NHL Debut

After years battling through the AHL, Oakville’s Curtis Douglas finally broke through, making his NHL debut Thursday night with the Tampa Bay Lightning against the Ottawa Senators. The towering 6'9 forward made an immediate impression by dropping the gloves with Ottawa’s Kurtis MacDermid on his very first shift, adding a shot on goal and logging 5:09 of ice time.

Drafted in 2018 by Dallas but left unsigned, Douglas signed AHL deals before earning his first NHL contract with Toronto in 2022. After a stint in Arizona’s system, he was picked up on waivers by Tampa Bay this fall. Now, the former Marlie is living his dream in the big leagues.

Wednesday, October 15
🌤️ Cooler with clouds then sun
High: 14 °C | Low: 5 °C

Thursday, October 16
☀️ Sunny
High: 14 °C | Low: 7 °C

Friday, October 17
☁️ Considerable cloudiness
High: 15 °C | Low: 11 °C

💃 Dance Essentials Class
Wed 10/15 @ 6:30PM-7:30PM
Taste of Colombia, 67 Bronte Rd

🎤 It’s My Party! – Starring The Lovettes
Wed 10/15 @ 7PM
Oakville Centre for the Performing Arts

📚 Cookbook Club – Indian Desserts
Wed 10/15 @ 7PM-8PM
Iroquois Ridge Branch Library

🎬 Movie Night – The Cure: An Inside Job
Wed 10/15 @ 7PM-9:30PM
Divinity Wellness

🎨 Mosaic Tray Table Course
Thu 10/16 @ 9:30AM-12:30PM
Elena’s Garage Studio

🪔 Diwali Workshop: Decorate Your Own Diyas
Thu 10/16 @ 12PM-1:30PM
The Women’s Centre of Halton

📚 Adult Book Club – The Summer Between Us
Thu 10/16 @ 6PM-7PM
Oakville Public Library

🎃 Oakville Ghost Walks
Thu-Fri 10/16-10/18
Oakville Historical Society

🎨 Paint Nite: Autumn Tree Reflections
Thu 10/16 @ 7PM-9PM
2021 Winston Park Dr

🎵 In Memory of Ziad Rahbani – MWBF2025
Thu 10/16 @ 8PM-10PM
Oakville Centre for the Performing Arts

🥕 Burlington Farmers’ Market
Fri-Sat 10/18-10/19 @ 8AM-2PM
Burlington Centre

🎭 Middle Raged
Fri 10/17 @ 8PM
AEG Liebherr Auditorium

🏡 Oakville Fall Home & Lifestyle Show
Fri-Sun 10/17-10/19
Oakville Place

📸 Free Family Photo Session
Sat 10/18 @ 9:30AM-11:30AM
Valleyridge Park

🏃 5K Run to Rise
Sat 10/18 @ 9AM
Coronation Park

🎃 Acorn Fest – Halloween Edition
Sat 10/18 @ 12PM-6PM
Towne Square

🐶 Tails & Treats 2025
Sat 10/18 @ 12PM-1PM
Towne Square

🪔 5th HCF Deepawali Mahotsav 2025
Sat 10/18 @ 12PM
OE Banquet Hall & Conference Centre

🚶‍♀️ Oakville & the Underground Railroad Walking Tour
Sat 10/18 @ 1:30PM-3PM
Oakville Museum

🎤 A Night at the Opera – Masterworks of Oakville
Sat 10/18 @ 8PM
St. Matthew Catholic Church

🎸 Mike Branton & Trish O’Neill – Space Jam
Sat 10/18 @ 8PM
The Moonshine Café

🎶 The RadioSonics – Rock! Dance! Party!
Sat 10/18 @ 8:30PM-11PM
The Oakville Pump & Patio

🎸 Tom Morello – A Night of Stories & Music
Sat 10/18 @ 8PM
Oakville Centre for the Performing Arts

🎵 Rock Covers Night – Quietly Violet
Sat 10/18 @ 9PM
Tin Cup Sports Grill

👗 St. Joseph’s REFLECTIONS Fashion Show
Sun 10/19 @ 12PM-4PM
300 River Oaks Blvd E

💼 Empowering Financial Literacy Networking Event
Sun 10/19 @ 1:30PM
2020 Winston Park Dr, Unit 404

🎤 Sinatra 110th – All The Best
Sun 10/19 @ 2PM
Oakville Centre for the Performing Arts – 130 Navy St

🪔 Oakville Diwali Bazaar
Sun 10/19 @ 3PM-11PM
1280 Dundas St W

💎 Charm Jewelry Workshop
Sun 10/19 @ 3PM
150 Oak Park Blvd

❓ Trivia

Thank You!

Thanks for reading the Oakville Digest today. If you found something useful, share it with someone who is getting their house ready for Halloween.

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NICK POLLOCK
Founder / The Oakville Digest
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