Races near Oakville, ON, Canada Discover all endurance events in Oakville, Canada! Find marathons, triathlons, 5Ks, cycling events, and more. Get ready to challenge yourself in the heart of Oakville. 19 Sep 5 Peaks Ontario Race 5 - Heart Lake Brampton, Ontario L6Z 0B7, Canada 21 Sep Schomberg Mug Run Schomberg, Ontario L0G 1T0, Canada 21 Sep Strides for Sanctuary Toronto, Ontario M4M 3M9, Canada 28 Sep YMCA Charity 5K GTA North York, Ontario M3K 2C5, Canada 28 Sep Ron Moeser Memorial Fun Run Scarborough, Ontario L1W 2M9, Canada 28 Sep 5 Peaks Cider Run Uxbridge, Ontario L9P 0L1, Canada 29 Sep Fall 5 KM Classic Waterloo, Ontario N2L 2Z4, Canada 29 Sep BIST Hero 5K Run, Walk and Roll North York, Ontario M3C 3L7, Canada 05 Oct PUMA Toronto Women's 8k/5k North York, Ontario M3C 3L7, Canada 12 Oct Crystal Beach 5K Crystal Beach, Ontario L0S 1B0, Canada 20 Oct New Tecumseth Memorial Run Alliston, Ontario L9R 1E4, Canada 20 Oct Pumpkinfest Walk, Run & Roll Waterford, Ontario N0E 1Y0, Canada 20 Oct Art In Motion 10K/5K/2K Vaughan, Ontario L4L 2V8, Canada 20 Oct Rotary Turkey Trot Oakville, Ontario L6M 4J7, Canada 27 Oct Wild Mile Toronto, Ontario M4V 2V6, Canada 16 Nov The Santa Pur-suit Waterloo, Ontario N2J 1P2, Canada Explore Race Destinations