No matter your mode of transportation in Toronto, you’ve likely used one on your daily commute: a road, a street, an avenue…maybe even a cul de sac. The route we take sometimes becomes so familiar, we don’t even think about which street we’re on when we’re on it – but each one has a name, and each name has a meaning.

The history of some roads and their subsequent naming might sometimes be obvious. Most streets are named for people, whether or not they ever visited Canada. Some are named for landmark houses in the area or the hometowns whence settlers came. John Street, Simcoe Street and Graves Street were all named for the founder of York (that’s John Graves Simcoe). Bathurst Street, once a lane connecting a farm to the then-town of York, was named for an earl who never visited Canada. Spadina Avenue – which historically was pronounced Spadeena – was named for a house on top of a hill, honouring an Ojibwa word meaning high place.

Learn about the meaning behind the names of the following streets to impress your friends, or the guy sitting next to you on the streetcar who probably doesn’t want you talking to him so much.



Alexander Street

Carlton/Yonge



(Photo by Bradley Woods)

Named for Alexander Wood, a Scot with an imported goods shop on the northwest corner of King and Frederick where the first sidewalk of Toronto was laid. He was a popular guy who was respected as a magistrate until a sex scandal in 1810. While investigating a rape case, he inspected the genitals of several young, male suspects after the victim said she had scratched her assailant. It wasn’t publicly recorded that Wood had acted indecently, or that he was gay, but the town talked and even created a nickname for him, Molly Wood, that became “molly,” a snide insult for homosexual men. Wood later owned 50 acres of land at Yonge and Carlton Streets, which locals named Molly Wood’s Bush. Part of it would have been located in today’s gay village at Church and Wellesley, where Alexander Street, Wood Street and Alexander Place are, and where a statue of Alexander Wood stands.



Bay Street

Queen’s Quay to Davenport between Yonge and University



(Photo by Andy Burgess)

The centre of Toronto’s financial district wasn’t always so distinguished. Instead, it was named Bear Street for numerous bear sightings during the early days of the city. At least one report claims the street, which connected to the bay in the harbour, was so-named for an instance in which a bear was chased from the surrounding woods in the area to the waterfront. Bay Street was named in 1797.



Bloor Street

Broadview to Dixie between Queen/Queensway and Eglinton



Joseph Bloore was an Englishman who owned the Farmers Arm Inn, near the St. Lawrence Market, and then a brewery on land he owned near what is Sherbourne Street today. Together with William Jarvis (Jarvis Street was named for his cousin, Samuel), he founded the village of Yorkville in 1830 for people looking for fresher air outside of the town of York. Today, Bloor Street (no one is really sure where the ‘e’ went) is approximately 25 kilometres long and includes the Mink Mile, which is the most expensive place in Canada to lease retail space.

A plaque commemorates Joseph Bloore’s contributions at St. Andrew’s United Church on Bloor Street East. He is buried in Necropolis Cemetery.



Blue Jays Way

Front/Spadina



(Photo by fw_gadget)

Originally, this street was an extension of Peter Street, named for Peter Russell, the first administrator in York. In 1993, the Toronto Blue Jays won their second World Series championship at the Skydome (now the Rogers Centre), which was located at the end of Peter Street. Wayne Gretzky, who owned Wayne Gretzky’s restaurant on the same street, then pitched the name change idea to honour the team’s win(s). He hoped Wayne Gretzky’s could be located at 99 Blue Jays Way (honouring his hockey jersey number) rather than 41 Peter Street. Initially the request was rejected by the city services committee, who said the name change and renumbering would make it look like they were catering to the rich and famous. Eventually the request was granted, with the restaurant agreeing to put up a plaque explaining the renaming and honouring Russell’s historical contribution.



Christie Street

Bathurst/Bloor



William Christie was a biscuit maker’s apprentice in Scotland, and began working in a bakery in York soon after he came to Canada in 1848. In partnership with one of the bakery’s owners, he built an enormous factory at Adelaide (then Duke) and Frederick streets (now home to George Brown College) and became the largest manufacturer of biscuits in the country. Christie died in 1899, but his son took over the company, which sold to Nabisco in 1928. Christie Pits are also named after Mr. Christie. Knowledge makes cookies taste even better.



Cummer Avenue

Bayview/Finch



Juuuust in case you were wondering, the Kummer (sometimes Cummer) family left Germany because of their Lutheran religion, and then Pennsylvania because they were loyal to Britain after the American Revolution. They settled on land between Sheppard and Finch, east of Yonge, in 1797, and then built a sawmill on the Don River near Finch and Bayview in 1819. What is now Cummer Avenue was once just a lane for horses and buggies. The Kummers continued to grow and build their businesses in the area, often referred to as Kummer’s Settlement, over the next 50 years. After converting to Methodism and hosting spiritual meetings and Sunday School, the area now known as Willowdale was known as Scripture Town and Angel Valley. Descendants of the original Kummers were none-too-pleased when Cummer Avenue ended up on a Toronto-based condom design a few years back.



Danforth Avenue

Kingston Road to Broadview between Gerrard and O’Connor/St. Clair



Asa Danforth Jr. was one of the first citizens in Onondaga County in New York when he arrived there from Massachusetts in 1788. He fell into quite a bit of debt while speculating in land in New York State, so he moved to Upper Canada. Here, he was commissioned by administrator Peter Russell (of Peter Street fame) to build a much-needed hundred-mile road between York and Kingston at a cost of $90 a mile. Danforth is credited for cutting the first road through thick forests in Scarborough. He built Danforth’s Road by 1799, but continued to be heavily in debt and wasn’t adequately paid by the Canadian government, who complained about the quality of the road and didn’t trust Americans at the time. As a result of the debt incurred from building Danforth’s Road and not being paid for it, Danforth gave up arguing for his payment and bitterly retreated to New York. The last records of him show he continued to face trouble for further debt, and he died around 1821. The roads he worked on are still in use as parts of Queen Street and Kingston Road. His Danforth Road in Scarborough and Danforth Avenue were both named for him, though he had no part in building Danforth Avenue.



De Grassi Street

Broadview/Queen



A side street in east Toronto is now forever associated with popular CBC shows The Kids of Degrassi Street, Degrassi Junior High, Degrassi High and Degrassi: The Next Generation, but it was named for either Captain Phillipe De Grassi or his son, Alfio, a well-known mason and merchant. Phillipe might have been one of the first Italians in the country, and chose farmland in the Don Valley in 1832 after serving with Napoleon’s French army in Spain and the British army in the West Indies. He wasn’t particularly experienced as a farmer, and once lived in a stable for some time with his family after a fire destroyed their home. De Grassi was a member of the Family Compact. His daughter, Cornelia De Grassi, was 13 when she spied on rebels gathered at Montgomery’s Tavern during the Rebellion of 1837. She was able to give Sir Francis Bond Head valuable information about the rebel numbers prior to him organizing his troops. Which makes us wonder if the street is actually named after her.



Dundas Street

Kingston Road to Dixie between Queen/Queensway and Danforth/Bloor



(Photo by hinter)

John Graves Simcoe, the founder of York, originally intended to have Dundas Street run as a military route from Detroit through London and York to Kingston in case of war with the Americans. It was built throughout the 18th century and named for the Right Honourable Henry Dundas, Viscount Melville, the British secretary of state for the home department, and previous Lord Advocate for Scotland. Dundas Street is made up more than a dozen smaller streets, which gives it a crooked feel throughout the downtown area. Notably, Dundas didn’t ever visit Canada (nor did George Yonge, who lent his name to Yonge Street).



Hubbard Blvd.

Queen/Woodbine



Frederick Hubbard was the general manager of the Scarboro Beach Amusement Park, a place designed to entertain fun seekers in the Beaches from 1907-1925. Initially, steamers brought park goers from the foot of Yonge Street in the city to the park, but in 1912, the Toronto Railway Company bought the amusement spot, which sat close to the end of the streetcar line. Now, the land is filled with subdivisions, but then it was a hotspot filled with attractions including roller coasters and rides, freak shows, circuses, costume parades, daredevil acts, refreshment booths, dance pavilions, band concerts and an annual six-day bicycle race. Hubbard Ave. is located where the park’s boardwalk sat while Scarborough Beach Boulevard is the street that was once the path to the entrance of the amusement park.



Leslie Street

Lake Ontario to Ivy between Cowell and Pape; Eglinton to Steeles between Don Mills Rd. and Bayview



George Leslie was a Scot who immigrated to Toronto in 1824. He worked as a builder on the Parliament Buildings and Upper Canada College. In 1834, Leslie co-founded the Toronto Horticultural Society. In 1837, he opened Upper Canada’s first seed store and operated the Toronto Nurseries in 1845 with his sons on about 200 acres east of the Don River. The gardens and some of the trees at Mount Pleasant Cemetery and in Allan Gardens, as well as some trees used in British shipbuilding, came from Leslie’s nursery. Many of the oldest trees were planted because of Leslie, and the city’s chestnut trees exist because of an oversupply – he sold them to the city at a discounted rate. Leslie was on the Toronto City Council, a member of the volunteer fire department, a founding member of the local Presbyterian church and he also worked as postmaster in the neighbourhood that became Leslieville in 1860. Kinda makes you wonder what you’re doing with your life, huh?



Montgomery Avenue

Yonge/Eglinton



It’s impossible to scratch the surface of Toronto’s history without John Montgomery’s tavern being noted. It was William Lyon Mackenzie’s Rebel headquarters during the Rebellion of 1837, and the site of the clash between the Rebels and Loyalists that eventually led to the legislative union of Upper and Lower Canada and responsible government. Montgomery wasn’t a supporter of an armed uprising, but was dragged into the consequences when he was arrested and tried due to being the tavern keeper despite being in the process of moving out. He was sentenced to be executed, and then instead deported. Prior to his exile, he cursed anyone involved in his unfair judgement by saying, “These perjurers…will never die a natural death, and when you, sir, and the jury shall have died and perished in hell’s flames, John Montgomery will yet be living on Yonge Street.” He outlived his accusers, and was compensated for just a portion of the loss of his business in 1873.



St. Clair

Kingston Road to Scarlett Road between Bloor/Danforth and Eglinton



(Photo by Hailey Toft)

The Grainger family rented a farm and owned a flower shop near what is now Avenue Road and St. Clair. After seeing a stage production of Uncle Tom’s Cabin, young Albert Grainger borrowed a misspelled name from the program to use as his middle name, which he didn’t have. He chose St. Clair, meant for the story’s hero Augustine St. Clare, who bought and set Uncle Tom free. That St. Clare is named for the Italian saint, founder of an order of Franciscan nuns called “Poor Clares,” who survived the Middle Ages and Industrial Revolution while living largely in silence and begging for alms. Grainger painted his new middle name on a sign and hung it on a tree on the farm, where it stayed even after his young death at the age of 20 due to complications of a cold. When surveyors later stumbled upon the sign, they assumed it was the name of the second concession and so it became St. Clair Avenue. In 1913, the St. Clare’s Church was built near Dufferin on St. Claire Ave. West by the Roman Catholic community.



Temperance Street

Queen/Yonge



(Photo by Commodore Gandalf Cunningham)

Jesse Ketchum was born in New York, but after being taken into a foster home when his mother died, he fled to Upper Canada and bought a tannery. He was known for being an extremely generous philanthropist and great contributor to the city of Toronto. He helped fund the rebuilding of Don River bridges, establish the Methodist church, and donated greatly to local schools, libraries and churches while also helping back in Buffalo. Because of his horrible experience with an alcoholic father, Ketchum was a strong supporter of the anti-liquor/Temperance movement, and so after the rebellion when he moved his tannery to New York he donated some of his land to be used for Temperance Hall on Temperance Street. He insisted alcohol should never be served on that street. His large, American-style house was destroyed in the late 1830’s. Ketchum’s name lives on at Ketchum Hall at Buffalo State College, Jesse Ketchum Junior and Senior Public school in Toronto and in Ketchum Manufacturing, a Brockville-based agricultural supply manufacturer founded by his descendants.



Need to know more? Pick up the Toronto Street Names: An Illustrated Guide by Leonard Wise and Allan Gould.



(Main photo by YU-JEN SHIH)