Spend 48 hours skiing, snowshoeing and skating through Oakville

Looking for some fresh air and new scenery this winter?

Embrace the outdoors in Oakville with this jam-packed itinerary of great food, incredible sights and winter sports. 

Note: This itinerary is based on information available in early November 2023. Please contact businesses directly to confirm details.

Day 1: Lakeside hikes and winter sights

Settle into your hotel of choice and then head into town for a belly-warming lunch at local favourites like Narenj, Plank Restobar or The Crepe Kitchen.  

Take to the lake and experience Oakville’s breathtaking winter landscapes from the shores of Lake Ontario. Lakeside Park, Tannery Park, Coronation Park and Bronte Heritage Waterfront Park provide some of the best paved pathways to explore the local lakeshore.

Grab a bite once you’ve had your fill of fresh air and defrost with a warm meal from Maro’s Bistro, The Firehall or Coriander Green.   

Spend your evening taking in the cozy sights in Downtown Oakville, Kerr Village or Bronte Village. Each neighbourhood is beautifully decorated with holiday lights and decor, making nighttime strolls an awe-inspiring experience during the winter months. 

Need a way to warm up? Book a time to swim in your hotel pool before laying your head down for the night. 

Day 2: Snowshoeing, skiing and skating, oh my!

Get started bright and early on your second day with a sunrise cross-country skiing or snowshoeing adventure! Oakville is home to plenty of trails perfect for these fun winter sports. Those looking to snowshoe will find a haven in Bronte Creek Provincial Park’s secluded trails.

Looking for more trail info? Download Visit Oakville’s Winter Activities Map for all the best info on local trails, winter sports, entertainment and accommodations.

Once your legs have tired, recharge with brunch at Community, Kerr Street Cafe or Stoney’s Bread Company before lacing up for an afternoon of skating. 

Indulge in a classic Canadian pastime at one of Oakville’s outdoor ice rinks and experience the beauty of Oakville’s winter views. There are many rinks dotted throughout town, so pick one or skip around to a few for different viewpoints throughout your trip. 

Treat yourself to one last dinner before leaving town. Don’t forget to stop by local spots like Sugar Suite Cakes, Black Forest Pastry Shop, The Sweetest Thing or Sweet! Bakery for some takeaway treats on your way out.

Share your experiences with us by tagging @VisitOakville in all of your Oakville adventures.