Oakville
Walking Events Calendar near Oakville 2026-2027
Monthly updates for Oakville
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Explore the top walking events near Oakville for 2026-2027! We've gathered 23 great walks in the area. Check out our detailed list below to find your next local walk.
July 2026
A park course at Confederation Beach Park starting at Willow Cove Pavilion offering a 5 km walk alongside the run, with onsite registration and bib pickup, refreshments on return, and free registration for kids 12 and under when accompanied by an..
August 2026
September 2026
Non competitive 1 km and 5 km walks at Christie Lake Conservation Area on park trails, family friendly and held to raise funds for local breast cancer research.
A walk along the Etobicoke Creek Trail in Brampton that starts and ends at Loafer's Lake Park, suitable for participants of all ages. Participants receive snacks and refreshments after the walk and early registrants receive an event shirt.
A 1KM family fun walk at Milton Community Sports Park, held as an in person charity event supporting Milton District Hospital. Walkers follow an easy park route alongside the 5KM run in a family friendly community atmosphere.
Walk options of 5 km, 2.5 km and 1 km start at 176 Robert Speck Parkway; the main route is a scenic 5 km loop through Mississauga Valley Park. Family friendly with shorter accessible routes available.
Walkers can choose a 2.4 km route starting at Milton Sports Centre on Santa Maria Boulevard, with human only or canine plus handler entries. The community course includes vendors, adoptable dogs and family friendly activities.
The event offers walkers 5K and 1K routes at Erindale Park in Mississauga, with in person options and a virtual option for the 5K, alongside the running races.
October 2026
The event offers a family friendly 1K walk at Spencer Smith Park in the heart of Burlington on park paths suitable for all ages. Walkers join alongside the running races to support the Joseph Brant Hospital Foundation.
Walking options include a community 1 Km walk and a 4K route starting at 1199 Upper Wentworth St, Hamilton, ON. The event gathers the local community and supports the Juravinski Hospital and Cancer Center Foundation, with walkers alongside th..
Walkers can choose 5K or kids 1K routes from McMaster Student Centre in Hamilton on an accessible, stroller friendly course with one water station at mid route.
The Hamilton Marathon Road2Hope includes walker routes of 5 km and 10 km starting from Confederation Park at 680 Van Wagner's Beach Rd along a waterfront course. Walks take place alongside the running races and include family walk/run options.
November 2026
Walkers follow the scenic Lions Valley trails on 5 km or 11 km routes starting at Upper Middle Park, Oakville, with rolling trail terrain. The event is rain or shine; early kit pickup at Neyagawa Park is planned and an unsupervised bag drop w..