Our sightrunning tours of Toronto explore the history, architecture, neighborhoods, and attractions of the downtown core and along the Lake Ontario shoreline! Our runs cater to runners of all skill levels. Sign up for your run below!



In partnership with Get Out There Magazine, we're bringing back our enormously popular 5k run to the Distillery District.

The December event sold out quickly so this time we're doing two runs, finishing at the Toronto Festival of Lights

As the Trip Advisor reviews will attest, this tour will make even a lifelong resident develop a deeper appreciation for Toronto, by bringing the city's past to life with colourful, largely forgotten tales.

OFFERED: Thursday, February 16th @ 6:30 p.m. AND Thursday, February 23rd @ 6:30 p.m. 

DISTANCE: 5.0 km / 3.1 mi

TERRAIN: City sidewalks.

ELEVATION: Mostly flat or slightly downhill.

TOUR DURATION: Approx. 60 minutes

MEETING LOCATION: Massey Hall (Victoria & Shuter), main entrance

Downtown sights


The most Toronto you can see in 10k! Mostly flat or downhill, this tour introduces you to the University of Toronto, Ontario Legislature, Royal Ontario Museum, Frank Gehry's redesign of the Art Gallery of Ontario, Queen Street West (Vogue Magazine's second favourite street), Rogers Centre (Skydome), CN Tower, the Ripley's Aquarium of Canada, New City Hall, Old City Hall, St. Lawrence Market (National Geographic's top pick for food markets), the Harbourfront and the site of Ontario's first Parliament Buildings, before ending at the historic Distillery District; a stunning Victorian-era collection of industrial buildings converted to galleries, cafés, boutiques and a brewery. 

OFFERED: Daily @ 9:30 a.m.

DISTANCE: 10.0 km / 6 mi

TERRAIN: City sidewalks and some grass. Down some stairs.

ELEVATION: Mostly flat or slight downhill.

TOUR DURATION: Approx. 90 minutes

MEETING LOCATION: Varsity Centre (Bloor St & Devonshire Pl), N.W. corner

Fenians & famine - $25 (CDN)

In the black summer of 1847, nearly 40,000 Irish came ashore in Toronto; a city of less than 20,000 people.  Many that survived the journey didn't last much longer and those that did still faced Old World intolerance and religious divides.  

But their arrival also inspired events that created Canada, and left us with colourful tales that are sometimes tragic and other times hilarious.

OFFERED: Thursday evenings / Sunday afternoons (please refer to the calendar)

DISTANCE: 8.5 km / 5.3 mi

TERRAIN: City streets, sidewalks, grass, some stairs

ELEVATION: Mostly flat with a few ramps & stairs

TOUR DURATION: Approx. 90 minutes

MEETING LOCATION: Black Toe Running (Bathurst & King)



If you're a pop culture or music junkie, you're going to love this tour. From the 1950s through the 1970s, Toronto was home to some of the biggest events and awakenings in popular music.  

It was here that John Lennon decided to break up the Beatles and the Prime Minister's wife disappeared for days with the Rolling Stones. Neil Young & Joni Mitchell found their voices in Yorkville coffee houses and Bob Dylan found his band, changing the sound of an entire generation.  Alice Cooper, Jimi Hendrix and Janis Joplin all have unique ties to Toronto. Learn their stories and so much more, in just 10k.

OFFERED: Every Wednesday at 7:00 p.m.

DISTANCE: 10 km / 6 mi

TERRAIN: City streets, sidewalks, & paved paths

ELEVATION: Mostly flat with some little rises

TOUR DURATION: Approx. 120 minutes

MEETING LOCATION: The El Mocambo (Spadina, south of College)