There’s a lot to love about the Olympic distance — it demands speed in ways that long course triathlon doesn’t, you can race several in a year and there are always lots on the race calendar for the duration of the North American triathlon season. We’ve picked five in Canada and the surrounding region that stand out and are worthy of your race bucket-list.

Toronto Triathlon Festival

“Rush hour redefined” — that’s the tagline for this downtown race which gives triathletes the unparalleled chance to ride on the major highways of Toronto with a a view of the CN Tower the whole way. The race, now in its fifth year, offers a sprint distance, relay options and now a draft-legal event, too. With Simon Whitfield endorsing the race, it’s always extremely well-run and is a must-do for any Canadian triathlete.

New York City Triathlon

Another big city triathlon, this race always sells out early and attracts a high calibre of multisport talent. You’ll swim in the Hudson River, ride through Manhatten’s west side and run through the iconic Central Park in this race. If you can manage to snag a spot, it certainly lives up to its hype.

Chicago Triathlon

The final big city race on this list is another that attracts one of the largest fields of athletes in the world. Chicago Triathlon, much like the city’s marathon, lets you explore the city in a completely unique way. There’s a Triple Triathlon Challenge for those wanting something more than the Olympic distance — you’ll race the equivalent of a half distance across three separate races over the late-season weekend.

St. Anthony’s Triathlon

This April race in St. Petersburg, Florida is a great early season destination race and a chance to escape the Canadian cold. It’s known as one of the most iconic races in the United States and draws an impressive pro field as well as age-groupers from all over. The Tampa Bay water can be a little brisk at that time of year but the course is picturesque and spectator-friendly.

Lobsterman Triathlon

Arguably the most well-known triathlon in the Northeast, Lobsterman has a classic, New England feel that separates it from some of the others on this list and makes for an exciting race weekend. This Maine race sells out every year and happens in September, so it’s a great late season option to make the most of the end of summer.