Historic Trails and Waterfront

Start at the Old Mill. A mill has operated here since John Graves Simcoe ordered the Kings Mill to be built in the 18th century. Cross the bridge to Étienne Brûlé Park, named for the first European to set eyes on Lake Ontario (1615). Take the Humber River Trail north, where numerous other mills operated, until you reach Old Dundas Street. At Humbercrest Boulevard, you’ll pass early Iroquois settlements and retrace the steps of French traders through the “Toronto Carrying Place,” which ultimately set the stage for permanent development. Humbercrest eventually ends, then picks up again as Old Mill Drive. Follow that to Bloor and head east to High Park. A gift to the people of Toronto long before it was part of the city, the park was once home to abundant wildlife.

When you get to the southwest corner of Grenadier Pond, cross at Ellis Avenue and head to the boardwalk. Heading east you’ll pass the spot where 300,000 people greeted Marilyn Bell as she became the first person to swim Lake Ontario. Further along you’ll pass the spot where American troops first landed during the War of 1812.

When you get to the footbridge near the wind turbine, take the stairs into the Exhibition Grounds and jog around Fort Rouillé (1750), then return along Prince’s Boulevard, through Prince’s Gate. Turn left on Fort York Boulevard, which takes you along the southern “shoreline” the British fort was built to protect. Head up to Front Street (so named because it ran along what was then the waterfront). Decades of infill created the foundation for the train tracks you now see. Once you cross Yonge Street, turn right and head south to the Esplanade. Continue east, past the St. Lawrence Market (1803) to Parliament Park. The first Parliament Buildings constructed in Canada stood here. Torched by Americans during the War of 1812, British troops retaliated by setting the White House ablaze a year later. Dan Grant is the founder of the run crew Run T.O. Beer. He also takes runners on historical running tours of Toronto. Follow him on Twitter, Instagram and Facebook @BrewScout