Visit Oakville winter itinerary

Escape to a winter wonderland in Oakville this year and soak in the charm of Oakville during the holidays! 

Tailor your vacation from our can’t-miss list or download our winter itinerary checklist below and see how much you can experience. 

Make Oakville home for the holidays:

• Light up your night with Oakville’s spectacular tree lighting ceremonies in Downtown Oakville, Bronte Village and Kerr Village. 
• Get the authentic holiday market experience at one of Oakville’s local pop-ups.
  • All Handmade Marketplace
  • Bronte Handmade Market 
  • Sovereign House Christmas Arts and Crafts Sale
  • Christmas at Colborne Craft Sale
  • Christmas Bazaar St Jude’s Church
  • Joshua Creek Heritage Arts Handmade Market
  • St. Luke’s Annual Christmas Bazaar
• March alongside Santa and his helpers at the Oakville Santa Claus Parade. 
• Experience Christmas like a Victorian at Bronte Creek Provincial Park.

New year, new adventures:

• Take part in a timeless Oakville tradition by taking the plunge into Lake Ontario at the Courage Polar Bear Dip. 
• Howl in the new decade with the coyotes at Bronte Creek Provincial Park.
• Start 2020 off with a walk in fresh snow at Bronte Creek Provincial Park’s #FirstDayHike.

Explore local lore during Black History Month:

• Visit the Oakville Museum and delve into local Black History with their permanent exhibits Freedom, Opportunity and Family: Oakville’s Black History and The Underground Railroad: Next Stop Freedom. 
• Participate in the Canadian Caribbean Association of Halton’s Black History Month lineup. Past years have included art showcases, film screenings and music sessions. This page will be updated with the latest information once available. 

Embrace winter sports:

• Tour through Oakville’s 12 outdoor skating rinks and explore the town by blade. 
• Get out for the early morning sunrise and try your hand at cross country skiing through Bronte Creek Provincial Park.
• Take in a game at Oakville’s beautiful Sixteen Mile Sports Complex during the Richard Bell Memorial Tournament or the Frank Sabatino Memorial Tournament. 

Raise the curtain on a dramatic winter:

• Take in one of three Tony Award-winning musicals being staged by Theatre Sheridan:
  • Nine
  • Newsies
  • Cabaret
• Catch Canadian collaborations at the Oakville Centre:
  • Crash Test Dummies
  • Hyprov: Improv Under Hypnosis
  • Lydia Persaud

Couples retreat: 

Book your romantic Valentines Day at Visit Oakville’s Top 5 Talk of the Town Best Fine Dining locations

1. Jonathans
2. Hexagon
3. Cucci
4. Seasons
5. Ricarda’s

Want to carry this list around with you? Download your digital copy below.

Oakville Winter Itinerary Checklist

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