Hamilton has hooked on to several nicknames through the years but none has ever been more fitting than “The Ambitious City.” That ambition was in its genes, tracing back to founder George Hamilton. George was one of four sons of Robert Hamilton, a Scottish businessman who landed a contract to supply goods to the British Army at Fort Niagara in 1780 which became the basis of the family fortune.

George Hamilton signed on to the War of 1812 when he was 24 years old and during his service likely gained knowledge that the creation of the Gore District was being planned for colonial Upper Canada. In 1815 Hamilton purchased 257 acres from James Durand with an eye towards building a town that would become the new district capital. New neighbour Nathaniel Hughson was all in on the scheme and together they offered land to the crown for a courthouse and jail. 

With help from Durand in the House of Assembly the Gore District was hatched on March 22, 1816 and the as yet non-existent Hamilton was named the district town. George got to work laying out a street grid for the townsite with 80 lots set up as homesites. Just being named a district capital was no guarantee for a young town’s success. Many a government in the North American frontier moved around in the early 1800s and private towns were especially vulnerable to such vagaries. 

Hamilton, motivated as much by the desire to keep his land valuable as civic pride, worked hard to ensure the survival of his town. The Burlington Canal was constructed in 1823 and the new court house was ready by 1827, at about the same time all his original lots were finally sold. He established an important market and added more building lots from his land. George Hamilton died in 1836, not living to see his namesake town achieve Official City status a decade later but he had put the venture on solid footing.

One of the last important things to happen during Hamilton’s lifetime was the chartering of the London and Gore Railroad on March 6, 1834. The line ran from Niagara Falls to Windsor and when it was opened in 1854 the then-named Great Western Railway (GWR) lopped 200 miles off the journey from New York City and Boston to the boomtowns of Chicago and Milwaukee. The GWR located its maintenance shops in Hamilton and the city’s industrial foundation was laid.

Soon there would be iron and steel mills. And then beer and tobacco and textiles. Procter & Gamble and the Beech-Nut Packing Company established their first operations outside the United States in Hamilton. Studebaker built an assembly line in the city. Hamilton was a working town, a union town, a progressive town. The first telephone exchange in the British Empire was set up here in 1878.

Most of the industry has shuttered now but Hamilton has segued into the service business, growing to over 500,000 residents with amalgamations of surrounding municipalities. Along the way the “Ambitious City” made a concerted effort to rid itself of the “Victorian rot” on the streets and embrace modernistic structures. To see the results of those efforts our walking tour of the hub of the Golden Horseshoe will begin at the point that George Hamilton designed to be the most important intersection of his nascent town grid, where King Street, the main east-west road, crossed James Street, named for one of Hughson’s sons and the principle north-south thoroughfare...

Gore Park
King Street

This triangular sliver of two blocks was intended by George Hamilton to be the centre of his new town, containing some of his land and some of Nathaniel Hughson’s. But Hughson never ceded his half and Hamilton’s block remained undeveloped, triggering a long history of wrangling over its use. There were lawsuits between the City Council and the Hamilton family and only a visit by the Prince of Wales in 1860 motivated officials to remove the garbage that had piled up there over the years. A fountain was installed and turned on for Queen Victoria’s birthday on May 24; it became the first of four fountains in the park and the latest, from 1996, is a replica of the original.

In 1893 the second block was finally acquired but the controversy surrounding the little greenspace has continued to swirl. The first monument was built that year to honour Canada’s first prime minister John Macdonald, who had died two years previously. A proud coterie of 20,000 showed up but the statue proved a deadly menace as it had been placed in the middle of John Street and was the cause of numerous accidents. It was hauled to the eastern end of the park where it remains today. 

In front of you, at the western end, the rendering of Queen Victoria by Louis-Philippe Hebert of Montreal was dedicated in 1908. The monument is shaded by several trees, including the last of the historic ash trees that once populated the park. Nearly 10,000 ash trees infected by the emerald ash borer in Hamilton were unceremoniously sawed down in 1983. Also removed at that time were subterranean European-style washrooms that had been hailed as the Best Lavatories in Canada by Today Magazine. Installed in 1913, they were filled in during 1984.


Commerce Place
1 King Street West

This is Exhibit A for ambitious Hamilton’s zeal for urban renewal. The Canadian Imperial Bank of Commerce built two identical aluminum and glass towers here in 1987 and 1990. To make room for this pair the sacrifice was Hamilton’s first skyscraper, built by the Bank of Hamilton. That venture was led by Scotsman Donald MacInnes who sailed to Upper Canada at the age of 16 in 1840. He became one of Canada’s leading merchants and organized the bank in 1872. The original quarters burned seven years later and after several moves the Bank of Hamilton landed here in 1892. The bank thrived, eventually opening more than 100 branches across the Dominion before being absorbed by the Canadian Bank of Commerce in 1923. When eight floors were added to the head office here in 1905, Hamilton had its first high-rise.

Exhibit B is the corner facing Gore Park on the south side. Here the Canada Life Assurance Company raised such a magnificent Victorian pile in 1883 that Oscar Wilde called the five-story turreted brownstone confection “the most beautiful building in all of North America.” Nonetheless, amidst howls of protest, it was demolished in 1973. It was known as the Birks Building by then and the clock from the tower was saved and shuffled over to Jackson Square across the street.  


Lister Block
northeast corner of James Street and King William Street

While the blocks in this area seem somewhat desolate today this part of town was so happening in the middle of the 19th century that merchant Joseph Lister invested in a four-story commercial block for his business in 1852. The Haymarket, now Jackson Square, was across the street and the federal post office and city hall down the block. The eye-catching City Hall was destroyed in 1961 to make way for what is now part of City Centre. The Lister Chambers was one of Canada’s first indoor shopping arcades and became a focal point of Hamilton’s thrust towards big city status. 

Fire erupted in the store in 1923, drawing every firefighter and every piece of apparatus in the city. It was the worst conflagration Hamilton had ever seen and before it was over 80 businesses were destroyed. Joseph Edmond Lister vowed to rebuild what would be “undeniably one of the finest and most modern business structures in the Dominion.” He hired celebrated industrial architect Bernard Prack for the task and he delivered a Neoclassical six-storey ornament with dark brown rug brick wrapped with ivory terracotta on the lower two floors and cornice. Copper alloy spandrels accompanied the double-hung windows. The Lister Block closed in the 1990s but managed to dodge the wrecking ball for two decades until a multi-million dollar restoration arrived.

Hamilton City Centre
77 James Street North

Timothy Eaton’s retail empire spawned a chain of downtown shopping malls across Canada in the 1970s and 1980s. While some thrived, Hamilton’s always battled red ink. After Eaton’s fell into bankruptcy in 1999 the nameplate was retired and Hamilton City Centre became the purview of independent local retailers.

Federal Building
72 James Street North

This quirky hybrid of a building was constructed in 1856 as a classically-styled post office built of cut stone. It actually did temporary duty as Hamilton City Hall for a few years in the 1880s during a government relocation. After that the Sun Life Assurance Company, Canada’s first insurance firm and started in Hamilton, moved in and started remodeling. In the 1920s the insurance men decided to expand and rather than live with a sympathetic addition a completely different two floors of Edwardian Revival styled offices were added on top. 


Orange Hall
175 James Street North

The Orange Order is a Northern Ireland Protestant fraternal organization founded in 1795 to celebrate King William’s victory at the Battle of the Boyne on July 12, 1690. On that day he vanquished the Jacobites and cemented British control of Ulster. The first Orange lodges began springing up in Hamilton in 1840. The Hamilton Orange Society was so flush by 1905 that they were able to spend $20,000 on this ornate four-storey building with pressed brick and stone trim. William Palmer Witton designed the clubhouse which includes a classical nook on the second floor for a triumphant King William to stand. Since 1969 it has been the social club of the Vasco da Gama Futebol Club. 

John Weir Foote Armoury
200 James Street North

John Weir Foote was four years old when this sprawling armoury was completed on James Street. Department of Militia Chief Engineer Henry James designed the original North Drill Hall in the Italianate style in 1888 when Hamilton was considered crucial as a military centre and first line of national defense. In 1905 it was decided a second drill hall was needed and a much larger section constructed to the south side. In addition to the drill hall there were classrooms, recreational facilities and modern washrooms. The James Street Armoury was considered state-of-the-art for its time. Foote hailed from Madoc, Ontario and enlisted in the Canadian Army in 1939. He was posted to the Royal Hamilton Light Infantry as a Regimental Chaplain and became the only Canadian chaplain to be awarded the Victoria Cross in World War II. After saving many lives on the battlefield at Dieppe, France on August 19, 1942 Foote then surrendered to the Germans so he could continue ministering to the wounded in captivity. 


Commercial Block
56 York Boulevard at northwest corner of McNab Street

York Boulevard predates the city of Hamilton; George Hamilton retained the serpentine military road when he created his street grid. This block-filling Renaissance Revival warehouse was raised in 1858 to contain the burgeoning grocery and dry goods business of John Young. Young gave the commission to Frederick Rastrick, a British architect whose father John had been an iron founder and engineer instrumental in building some of the first railway locomotives. After a peripatetic first 33 years of his life the younger Rastick settled in Hamilton in 1852 and this was his first major commission.

Although there is not much competition, the Commercial Block earns its reputation as the “finest surviving pre-Confederation building in Hamilton” honestly. The mass of the structure is lessened by the organization of pavilions and an interior courtyard. The interior is graced by some of the first cast-iron column supports used in Canada. Clothing manufacturer John Calder converted the building to industrial space in the 1880s and in 1883 George Coppley, E. Finch Noyes and James Randall bought the Calder operation. The Coppley Apparel Group continued to manufacture clothing on the premises into the 21st century. Save for the sympathetic addition of a mansard roof early on, the masterwork of F.J. Rastrick has been little altered. 

Hamilton Farmer’s Market
35 York Boulevard

The Hamilton Farmer’s Market began operation in 1837 after Andrew and Mary Miller gave the city some land for such a purpose. By 1885 the market was operating year-round in a Victorian showcase with spires and a copper-topped dome. Market Hall burned in 1917 but stalls at York and McNab with meats and eggs and butter were soon operating in an open air market that was said to be the largest in Canada. The stalls were shut down for a parking lot in the 1960s before the Market landed in its current digs in 1980.

Philpott Memorial Church
84 York Boulevard at northwest corner of Park Street

Peter Wiley Philpott was a sometime blacksmith and construction worker who came to religion through a Salvation Army meeting in Dresden in 1884 at the age of 18. He became a street preacher with the Salvation Army and arrived in Hamilton in 1892 to begin a mission for the many industrial workers. His sermons attracted great crowds and his congregation - which numbered no wealthy donors among its numbers - purchased property on this corner in 1901 for $2,500. Another $6,000 enabled the construction of the Christian Workers’ Chapel. A good wage at the time was a dollar a day. The new building proved too small and somehow $30,000 more was found to add an auditorium with a capacity of 1,200 in 1906. It was renamed The Gospel Tabernacle. Dr. Philpott was lured away to Chicago in the 1920s and after his death in 1957 the church was renamed in his honour. 

First Ontario Centre
101 York Boulevard at southeast corner of Bay Street

The Hamilton Forum, also known as the Barton Street Arena, was the city’s sports palace beginning in 1910. In 1977 when the 2800-seat facility suffered a breakdown in its ice-making machinery the city decided it was cheaper to build a new arena than buy new equipment. Thirty-six million dollars and six years later came Copps Coliseum, named for long-time mayor Victor Copps. There were dreams of a National Hockey League franchise but being less than an hour’s drive from Buffalo and Toronto the city had to settle for some regular neutral-site big league games. In 2014 FirstOntario purchased the naming rights.


The Regal Hotel
152 King Street West at northwest corner of Bay Street

This Italianate-style commercial building was constructed on land deeded by Sir Allan MacNab, perhaps as early as 1847. It lays claim to having been one of Hamilton’s earliest hotels with names such as the Hamilton House, the Florence, the Palm Hotel and Lager Beer Salon, the Fairchild Hotel and The Dressel Hotel. The last of the long-departed guests knew it as the Regal Hotel, beginning in 1906. 

Art Gallery of Hamilton
123 King Street West at southeast corner of Bay Street

This is the third home for the Art Gallery of Hamilton that was founded in 1914 and is now the oldest and largest public art collection in southwestern Ontario. The exhibition space dates to 1977 and was expanded in 2005 with a design by local architect Bruce Kuwabara. The works of another Hamilton artist, William Blair Bruce, were key to the formation of the collection. After growing up in Hamilton for his first 18 years Bruce went to Paris in 1881 and became one of the first Canadian-born impressionist painters. 


Hamilton City Hall
71 Main Street West

The address for the current Hamilton City Hall, dedicated in 1960, was not a whimsical choice. So many buildings were torn down to make way for its construction that the numbers 55 through 105 were opened up on Main Street West. The number 71 was selected because that was the number of years the previous government home on James Street was in operation. Stanley Roscoe provided the modernist, International Style plans.

Hamilton Public Library
55 Main Street West

As his career was winding down, steel magnate Andrew Carnegie was ready to sell off his empire. He sat with financier J.P. Morgan who asked the Scottish industrialist how much money he wanted. Carnegie wrote $400 million on a slip of paper and passed it across the table. Morgan glanced at it and said, “Congratulations Mr. Carnegie. you are now the richest man in the world.” Carnegie then set about giving away as much of his fortune as possible. His pet project was public libraries and he funded over 2,500 across the world. In Canada 125 were built, 111 of them in Toronto. The grant for Hamilton’s library came in 1909 and was for $100,000 - only Toronto received a larger bequest. Architect Alfred W. Peene designed the stately Neoclassical building that replaced Hamilton’s main library that had been constructed in 1889 as the first in Canada designed solely to hold books. Hamiltonians borrowed their reading materials here until 1980.  

Centenary United Church
24 Main Street West at northeast corner of MacNab Street

The cornerstone for this Italianate-styled red brick church was laid in 1866. The first services were held in 1868 that happened to be the 100th anniversary of Methodism in North America and so the congregation in Hamilton named Centenary. In 1925 the Presbyterians and Congregationalists merged to form the United Church of Canada. 

Sun Life Building
22 Main Street West at northeast corner of James Street South

This early Chicago Style building with orderly fenestration was constructed in 1905, Th econvention of the ay was to design towers in the manner of a classical column with a defined base (the lower floors), an unadorned central stories (the shaft) and a decorative top floor and cornice (crown). The Sun Life Building followed the playbook perfectly.  


Pigott Building
40 James Street South

The Pigott Building represents the next generation of skyscrapers that stressed verticality. The Gothic-inspired Art Deco tower completed in 1929 was the masterwork of the Hamilton architectural team of brothers Bernard and Frederick Prack. The Prack family of industrial architects and engineers were natives of Pittsburgh, Pennsylvania but were extremely active in Hamilton and Ontario. The 18-storey tower was the tallest building in Hamilton and the city’s first steel-skeleton skyscraper. The price tag of $1,000,000 was picked up the Pigott Construction Company, also a family affair. Joseph handled the money and Roy took care of the engineering details. Together they built Canada’s largest privately owned construction business. In the 1970s the landmark tower fell into disrepair and seemed not long for the Hamilton streetscape - even the building’s hardware was sold off. But in the 1980s the property was linked with the Sun Life Building next door as a condominium complex and within a year the 109 units were 90% sold.  


Landed Bank & Loan Company
47 James Street South

This banking temple is the oldest remaining financial building from the early 20th century when such buildings were intended to project power and safety to potential depositors leery of trusting their money to strangers. The imposing fluted Corinthian pilasters are carved from Indiana limestone like the rest of the exterior. The Beaux Arts vault was designed by Charles Mills and completed in 1908. Mills was a leading Hamilton architect in the prime of his career at this time and he borrowed heavily for the Landed Bank & Loan Company building from the monumental Knickerbocker Trust Company Building on 5th Avenue in New York City. That architectural treasure did not survive modernization but this disciple stands much as it did a century ago.


Bank of Montreal
1 Main Street West at southeast corner of James Street South

Another Neoclassical ornament from this intersection’s halcyon days as the city’s banking and insurance heart, the Bank of Montreal’s main Hamilton branch arrived in 1928. The bank’s go-to architect, Kenneth Guscotte Rea, drew up the plans. The building is accented by Corinthian pilasters that lead to the main entrance on James Street which boasts a richly carved pediment featuring the Bank of Montreal coat of arms in the tympanum. The pediment is supported by a quartet of fluted Corinthian columns.

Saint Paul’s Presbyterian Church
56 James Street South at northwest corner of Jackson Street

William Thomas designed this textbook English Gothic style church building in 1857. Thomas had been born in England in the 18th century and this was one of his last projects before dying in 1860; he was Toronto’s city engineer at the time. The gray limestone came from local quarries and the 180-foot steeple is fabricated entirely of stone; it is the largest of its kind in Canada. The church bell was the first to ring in Hamilton. The congregation formed in 1830 among Scottish immigrants and was initially called St. Andrew’s.

James Street Baptist Church
southwest corner of James Street South and Jackson Street

One of Ontario’s leading ecclesiastical architects, Joseph Connolly, designed a Gothic style church for Hamilton’s Baptists in 1878 to mimic the appearance of Saint Paul’s. The heritage building was pulled down with the idea of saving the facade to be incorporated into a new building. 


Toronto, Hamilton & Buffalo Railway Station
36 Hunter Street East
The Toronto, Hamilton and Buffalo Railway (TH&B) was chartered in 1884 to link Toronto to the International Railway Bridge for local lines into the United States. After a few false starts the first trains rolled in 1892 and reached Hamilton two years later. When the line was completed in 1895 it was promptly bought jointly by two railroad powerhouses, the Canadian Pacific Railway and the New York Central Railroad. This is the second passenger station built by the TH&B in Hamilton, raised in 1933. Alfred T. Fellheimer, who was the lead architect for Manhattan’s fabled Grand Central Terminal, and Steward Wagner provided the distinctive Streamline Moderne style for the station. The last TH&B passengers boarded on April 26, 1981 and the facility became a centre for GO transit buses and trains.   


Tim Horton’s
257 Main Street East at southwest corner of John Street

Tim Horton’s is more than a coffee and doughnut chain; it is a Canadian institution. And the first store opened in Hamilton in 1964 about a mile from here at 65 Ottawa Streets North. Tim Horton was a physical defensemen for the Toronto Maple Leafs for over 20 years. He was a National Hockey League All-Star three times and skated around the ice with the Stanley Cup four times, including the last time Toronto won the championship. His first foray into post-hockey life was investing in his brother’s used car dealership but Tim Horton Motors was a bust. He then hooked up with Jim Charade who had a struggling shop called Your Do-Nut in Toronto and was looking for a celebrity endorser. 

The newly named Tim Horton Do-Nut failed but the duo decided to try again outside of the crowded Toronto market. Charade landed in Hamilton in an abandoned Esso service station and Tim Horton’s began selling a coffee and doughnut for a quarter and a box of a dozen fried pastries for 69 cents. That was some 4,000 stores ago. Tim Hortons serves more than 2 billion cups of coffee each year and Canadians drink more coffee per capita than just about any country on the planet. The chain collects 25 cents of every dollar spent on fast food in Canada. The Canadian Oxford Dictionary even contains an entry for “Double Double” - the go-to Tim Hortons order of “a coffee with double cream and double sugar added.”

Dominion Public Building
northwest corner of John Street and Main street

William Russell Souter and Gordon J. Hutton were versatile Hamilton architects in the 1920s and 1930s. After winning the commission for this government building in the 1930s they delivered an Art Deco manifestation of stripped down classicism appropriate for the times. It was part of a general program of putting the citizenry to work on public projects. While austere on the outside, save for bas relief carvings of men at work, the postal lobby inside in resplendent in brass fittings, marble and ceramics. When opened on September 21, 1936 there was room for the offices of Customs, Taxes, Immigration, Colonization, Relief, Pensions, National Health and the Royal Canadian Mounted Police. The post office shut down in 1991 and eight years later the space was converted into the John Sopinka Courthouse.  

Royal Connaught
112 King Street East at southwest corner of John Street

Harry Louis Frost dreamed of giving Hamilton a grand hotel. He had been born in Ohio and was on the road as a salesman for Jones National Fence by the time he was 15 years old. He came to Hamilton in his early twenties and started the Frost Wire Fence Company. The business was so successful that in 1909, when Frost was 35 years old, he rented a railcar and took his employees on holiday to California. In 1914 he broke ground on his dream hotel.

The first guests checked in on June 5, 1916. The Royal Connaught - it was named for the Duke of Connaught who was the Governor General of Canada at the time - was the tallest building in the city with 12 storeys. There were 244 guest rooms and each had marble on the bath floors and brass beds in the sleeping areas. The banquet hall could serve 1500 with elbow room to spare. A rooftop restaurant provided views of Lake Ontario and the Niagara Escarpment. Over the years prime ministers, Hollywood stars and business tycoons would sign the Connaught register.

Frost was a victim of the Spanish influenza epidemic and died in 1919 at the age of 45 but his hotel soldiered on, encompassing the building next door. The Royal Connaught shuffled through several owners and eventually began drooping in the 1980s. The last guest checked out in 2004. In 2008 developer Harry Stinson had a dream for the hotel as well - he was going to use the Edwardian-styled landmark as the base for a 100-storey, 1,000-foot tower, twice as high as any building in Hamilton. The plans fell through but the property is being repurposed for residential use.