One glance at a map and you realize there had to be a Windsor. Lake Erie and Lake Huron are so close that a settlement was natural to facilitate a continuous water route through the Great Lakes. That settlement arrived in 1748 in the form of a French Jesuit mission. The city it spawned is the oldest continually inhabited city west of Montreal.

It wasn’t Windsor yet, however. At least by name. When the first formal strides towards citydom took place after the British took control and the village was called Sandwich when it started in 1794. With expansion and the assignment of the Essex County seat it would eventually assume the name of the Berkshire, England town and the original village of Sandwich would get its own town status in 1858. 

But the biggest influence on the growth of Windsor was not French. It was not British. It was American, specifically the Detroit auto industry. After becoming the “Automotive Capital of the British Empire” the population of Windsor spurted from 10,000 in 1900 to 100,000 in 1925. The Ford Motor plant was established in 1904 and grew so large, at one point employing 14,000 people, that it became its own town known as Ford City.

It was not the first time an American industrialist spawned a municipality on the Canadian side of the Detroit River. Hiram Walker, a Massachusetts man, settled in Detroit and began buying land in Ontario in 1856. He moved to Canada in 1859 to build the Windsor Distillery and Flouring Mill, the surrounding town called Walkerville and a rail line to service his business. Walker moved back to the United States in 1864 but his distillery continued to crank out Canadian Club Whisky, the Dominion’s best-selling exported whisky. In 1935 Sandwich, Ford City and Walkerville all folded into the Windsor jurisdiction.      

Windsor has always been defined by its geography on the doorstep of America - it was a hot spot during the War of 1812, it was a major destination for escaped Southern slaves and it was a primary supplier of illegal liquor during the 1920s during the era of American Prohibition. Appropriately we will thus start our walking tour of the southernmost city in Canada where unobstructed views of the Detroit skyline are the main attraction... 

Festival Plaza
Detroit River at Ouellette Avenue

What were once a collection of bustling rail yards along the Detroit River were converted over the years into a waterfront necklace of parks nearly five kilometres long stretching from the Ambassador Bridge to Hiram Walker’s Canadian Club distillery. A serpentine bike trail traverses the greenspace and there are plenty of places to drop a fishing line right from the banks. Festival Plaza, on the east side of Ouelette Avenue, is mostly paved and takes it name from the many concerts, street performances and celebrations that fill the space here each year. 

The steam locomotive moored in the park is The Spirit of Windsor, a refugee from the CN Railyards in London, Ontario. It was one of about 75 locomotives facing destruction for scrap in 1961 when it was rescued, transported to Windsor, restored and put on display on May 7, 1963. Engine 5588 was built in 1911 and is a Type K3B Pacific 4-6-2, meaning it is configured with four leading wheels, six large driving wheels and two trailing wheels. The fountain in the plaza is a gift from Windsor’s sister city of Udine, Italy in appreciation for aid given to northern Italy following an earthquake in 1980.


One Riverside Drive
1 Riverside Drive West at southwest corner of Ouellette Avenue

This 14-storey glass-and-steel tower raised in 2002 is the current home of Chrysler Canada. The Greisler family was among the founders of Chatham, Ontario, receiving a land grant in 1798. When the family pulled up stakes to farm land in Kansas their German name was Americanized to “Chrysler.” Young Henry Chrysler was 12 years old when he ran off to join the Union Army in the American Civil War and after hostilities concluded in 1865 he came home to work in the local railroad shops. Henry’s son Walter tried many occupations but the mechanically-inclined youth never lost his fascination with locomotion and he found his calling with the nascent automobile industry in Detroit.

Walter Chrysler began his career with General Motors in 1910, as works manager for the Buick Division. His engineering wizardry soon earned him the reputation as a “car company doctor.” He worked his magic with the Maxwell Motors Company and Dodge Brothers Inc., which began in Windsor in 1897 when Horace Dodge invented a dirt-resistant ball bearing and began crafting Evans & Dodge bicycles on Ouellette Avenue. The Chrysler Corporation was formed in 1925 with cars being built in Windsor at a facility on Tecumseh Road where Jonathan Maxwell and Hugh Chalmers had manufactured cars since 1916. The windsor Assembly Plant opened in 1928 and remains the city’s largest employer.

Paul Martin Sr. Building
185 Ouellette Avenue at southwest corner of Pitt Street

This splash of Art Deco arrived on the Windsor streetscape in 1934 courtesy of the government’s attempts to stimulate the economy through large construction projects during the Great Depression. Windsor’s go-to architectural firm of Hugh Powers Sheppard and George Y. Masson took the lead on the design of the Dominion Public Building with help from John Edward Trace and Guy Buller-Colthurst. The stripped down classicism appropriate for the times showed itself in monumental fluted pilasters adorning the limestone walls. Look up to see Canadian crests on each of the street-facing facades. Long known as the “Post Office Building” the name was changed in 1994 when the letter delivery service moved to more modern digs. Naming honours went to recently deceased Paul Martin who was a 33-year Parliament Member of the Liberty Party of Canada and a professor of distinction at the University of Windsor. He is a “Sr.” because his son served as Prime Minster of Canada in the early 21st century. 


Equity Chambers
52 Chatham Street West

Ira Grinnell started his business career in 1872 selling sewing machines. He added musical instruments to his line in a new store in Ann Arbor, Michigan in 1879. With brothers Clayton and Herbert he came to Detroit in 1881. The Grinnell Brothers went into the piano-manufacturing business in 1902 and their Michigan plant was billed as the largest in the world. This brick building was constructed as a Grinnell music factory in 1911. The current Neocolonial appearance dates to the 1950s when the property received a makeover from Sheppard & Masson and did short-term duty as Windsor City Hall during a government move.


Security Building
267 Pelissier Street at northwest corner of University Avenue

Few architects left more fingerprints on Windsor than James Carlisle Pennington. He apprenticed early in his career with celebrated Detroit theatre architect C. Howard Crane. For this Colonial Revival ten-storey tower in 1927 Pennington teamed with John Boyde. It was one of the last of the first generation of high-rises that sought to replicate the image of a classical column with a defined base (the stone-clad first two storeys), shaft (unadorned brown brick middle floors) and crown (arched windows on the top floor and parapet on the roof). 
Capitol Theatre
121 University Avenue west at southwest corner of Pelissier Street

When the Vaudeville Theatre opened on New Year’s Eve, December 31, 1920 it was the largest single floor theatre in Canada with 1,995 seats. The stage was part of show business impresario Marcus Loew’s extensive chain of performance venues. New York architect Thomas Lamb, the man most responsible for creating the exuberant movie palaces of the day, designed the building. It was one of sixteen such palaces that Lamb built in Canada. The final price tag was $600,000 and required nine months to build. Two years after opening, Windsor’s premier entertainment destination became the Capitol Theatre. Gone With the Wind was the last movie ever screened here, in 1989. The Capitol dodged the wrecking ball and emerged as a performing arts centre after a $5.5 million makeover.


Bartlet Building Complex
52-98 University Avenue West

A chunk of the Batlet clan left Scotland for Upper Canada in the early 19th century and settled in what is today Amherstburg. The family moved to Windsor in 1854 as the village was incorporated. The next generation founded the venerable Bartlet and Richardes law firm and Edgar Bartet, in the generation after that, incorporated Ford of Canada in 1904. Edgar also bankrolled the construction of these properties on University Avenue. J.C. Pennington designed the classically-influenced building in the middle of the block in 1921 and three years later David John Cameron, who was instrumental in bringing English revival styles to western Ontario, drew up plans for the six-storey accompanying building on the corner. It boasts brown bricks and a Georgian Revival style stone wrap around the lower floors. 

Imperial Bank of Canada
285 Ouellette Avenue at northwest corner of University Avenue

Charles Sherman Cobb was a prolific bank architect in Toronto and he provided this Neoclassical vault for the Imperial Bank in 1920. The front facade is dominated by a pair of thick fluted Ionic columns. After its days of taking deposits ended the space was repurposed as The Bank Nightklub.   

Windstor Star
300 Ouellette Avenue at southeast corner of University Avenue

Jule and Jay Allen were brothers and energetic showmen who snared the Canadian franchise for Paramount films in the studio’s formative days. The Allens, using C. Howard Crane as their architect, moved rapidly to build top shelf theatres in every major Canadian city. Windsor received its Allen Theatre, with 1605 seats, on Ouellette Avenue on October 18, 1920. By that time the Allens had lost the Paramount franchise, triggering a bankruptcy in 1923. The theatres fell into the hands of Famous Players Canadian Corporation and the Windsor operator was Simon Meretsky. He re-named the movie house the Palace Theatre since the Famous Players had named their other property in town the Capitol after it was acquired from Loews. The Meretsky family shuttered the theatre in the 1980s and after shuffling through several owners the Windsor Star newspaper gave the aging theatre a $4 million facelift, including exchanging the stucco walls for glass, in 2012.

Windsor Armouries
353 Freedom Way at southwest corner of University Avenue

This flexing of military muscle arrived in 1902, designed with appropriately impressive castellated turrets by Federal Department of Public Works architect David Ewart. The walls are two-feet thick, rising from a massive stone foundation. A southern edition came along in 1935. Before this block-long red brick structure with imposing classical stone entrances was built, the Windsor military gathering place was a scattering of wooden buildings first constructed for Essex County in 1800. The interior has been refashioned as the home of the University of Windsor’s School of Creative Arts.

Greyhound Bus Station
44 University Avenue East

If you look closely - very closely - you still see vestiges of the sleek Art Moderne style in this 1940 bus terminal. It was the creation of local architects Hugh P. Sheppard and George Y. Masson, adopting the elements of the modernistic style which was all the rage at the time. The windows were paneled over in the 1970s and bus service ceased in 2007.

Tunnel Ventilation Building
70 University Avenue East

This 100-foot high structure was constructed to provide ventilation for the 1,570-metre Detroit-Windsor Tunnel. A similar structure is on the Detroit side. When completed in 1930, the immersed tube was the third underwater vehicular tunnel constructed in the United States. The Michigan Central Railway Tunnel had linked the two cities twenty years earlier. The brick-faced Ventilation Building has faint echoes of the Art Deco style that stresses verticality.

Windsor Cenotaph
City Hall Square East at University Avenue East

The Essex County War Memorial was originally dedicated to the lost soldiers of Essex County in World War I. Windsor architect George Y. Masson provided the design for the 20-foot high monument, fashioned from Canadian pink granite. It was originally located at Giles East and Ouellette Avenue but in 1965 it was taken apart stone by stone and rebuilt on this location.

All Saints Anglican Church
330 City Hall Square East at University Avenue East

Thanks to the efforts of the Reverend E.H. Dewar the village of Sandwich had an Anglican congregation early on, in 1852. When the first meeting house was raised in 1857 it was called “the prettiest church in Canada West.” The sanctuary served as a refuge for escaped American slaves on the Underground Railroad upon reaching Canada. As the military barracks across the street morphed into City Hall Square the church picked up a bell tower in 1875.


Windsor City Hall
350 City Hall Square West

The Central Public School was located here when the city decided to raise a new International Style city hall in 1955. It is now a government campus.


St. Alphonsus Church
85 Park Street at southeast corner of Goyeau Street

This congregation traces its roots to 1865 when its Romanesque-styled church was dedicated.


Canada Building
374 Ouellette Avenue
The largest office building in southwestern Ontario when it was raised in 1930 as a project of the Border Cities Star, as the Windsor Star was known at the time. Albert Harold McPhail, who hailed from Northern Ontario, won the commission and he delivered a 14-storey Art Deco office tower. Much of the decoration is reserved for the upper floors. The 70-metre Canada Building remained the highest building in Windsor until 1975.


Lazare’s & Company
493 Ouellette Avenue at northwest corner of Maiden Lane

Albert James Lothian designed this Art Deco retail space for the Reaume Real Estate Company in 1928. the most venerable tenant has been Lazare’s Furs, started by the Goldin family in 1925. The furrier’s neon advertising sign hanging in Maiden Lane has earned designation as a piece of Windsor heritage. It was first hung in 1942.

Pascoe Building
511 Ouellette Avenue at southwest corner of Maiden Lane

Across Maiden Lane is another Art Deco creation, this one designed by Pennington & Boyde for Pascoe’s Limited, a men’s clothing store. It boasts ziggurat patterns derived from ancient Egypt in the stone facade.


511 Pelissier Street

Recreational and residential facilities for both men and women in the same facility was a revolutionary idea in 1924 when Windsor built the first joint YMCA and YWCA in Canada. Architect David William Fair Nichols, in collaboration with Hugh P. Sheppard and George Y. Masson, delivered one of downtown Windsor’s best buildings for the project. His Italian Renaissance design features a carved stone porch above the entrance, ornamental ironwork and a handsome brick-and-stucco dressing.

Park Place Shops
405 Pelissier Street at southwest corner of Park Street

Down the street is another dollop of Italian Renaissance architecture. This three-storey structure with a stone base and reddish-orange brick was completed in 1908.


St. Andrew’s Presbyterian Church
405 Victoria Avenue as southwest corner of Park Street

St. Andrews formed in 1857 with 29 congregants. The first meetinghouse was not erected until eight years later, two blocks away on Chatham Avenue. Before that, there were services in local stores, homes and schools. St. Andrews relocated here in 1883 but fire destroyed the first brick church on this corner. Detroit architects Frederick H. Spier and William C. Rohns, known for their monumental railroad stations, sailed across the river to provide the Richardsonian Romanesque design for the congregation in 1895. The red brick church features several hallmarks of the style, including a square tower, turrets and powerful arched entrances. Due to a dwindling congregation St. Andrews was forced to sell its landmark home in 2016.

St. Clair College/TD Student Success Centre
305 Victoria Avenue at southwest corner of University Avenue

We take it for granted today but when the Guaranty Trust Company opened this branch in 1948 it offered depositors the “first teller’s drive-in window in Canada.”

Metropolitan/Guaranty Trust Building
176 University Avenue West at northeast corner of Victoria Avenue

Bank officers could keep an eye on the success of its drive-up window from across the street in its 10-storey headquarters. The Art Deco tower was built in 1928 and is another design from the busy drawing tables of James Carlisle Pennington and John Boyde. Faced entirely in brick, you can see the emphasis on verticality in the Art Deco style. You can also see the shift from traditional Renaissance high-rise architecture to Art Deco design by looking back at the firm’s Security Building at the end of the block, built just one year earlier. 


Labelle Terrace
309 Chatham Street West at southwest corner of Dougall Avenue

When James LaBelle, a physician, constructed this stylish townhouse of eight units in 1905 it fit right into the vibrant neighborhood. Today it is the sole survivor of that era to give a glimpse into how Windsor lived at the beginning of the 20th century.

Windsor International Transit Terminal
300 Chatham Street West

This barrel-vaulted bus station from 2007 replaced the earlier Greyhound station we saw on University Avenue. The tab for modernization after 67 years - $7.4 million.

Family Aquatic Complex
401 Pitt Street West

This showcase recreational centre came online is 2013 with a 10-lane pool and moveable bulkheads to accommodate any desired swimming competition. Also part of the complex is the Adventure Bay Family Water Park and the Windsor/Essex County Sports Hall of Fame.


François Baby House
254 Pitt Street West

Tucked inside a maze of modern structures is a National Historic Site of Canada, a rare Windsor heritage treasure. François Baby was born in Detroit in 1768, the son of local fur trader and Indian agent Jacques Baby who built one of the great fortunes on the western frontier of Upper Canada. François was a captain in the French-Canadian militia but was fighting on the side of the British when the War of 1812 rolled around. It was about that time that he started construction on this Georgian-styled manor house. Baby was captured by American forces and the unfinished house commandeered by invading troops. When Baby returned he found his house plundered and never did receive proper compensation for the damage. Baby lived into his eighties and war returned to his doorstep again in 1838 during the rebellion in Upper Canada known as the Patriot War. The Battle of Windsor concluded the affair after skirmishing in the Baby orchard resulted in the routing of some 140 American and Canadian invaders by Upper Canada militia. The house somehow trundled on unmolested until renovation took place in the 1940s, funded mostly by profits from Hiram Walker’s Club Whisky and eventually became home to the Windsor Community Museum.

University of Windsor/Windsor Star Buildings
181 Ferry Street at southwest corner of Pitt Street

The first editions of the Windsor Record hit the street in 1888. In 1918 the operation was purchased by W.F. Herman and the name changed to the Border Cities Star. Herman was of Nova Scotia stock, the son of a sea captain, but he fell into newspapering at an early age. After moving to Boston and marrying an American girl Herman determined to head to Saskatchewan to work the land. The story goes that his wife Adie believed her husband was only choosing that path for her sake so she sent a letter ahead to the Saskatoon Phoenix informing the publisher that a first-rate printer would be arriving shortly to scout for farm land. Herman was in Saskatoon only one day before he was at work on the paper, which he purchased in 1912. Even as publisher of the Star Herman could be counted on to show up in the press room from time to time to move type around. In 1923 the Star moved operations to this block, first in the brick building to the south, constructed in 1918, and then into the Beaux Arts offices on the northeast corner, designed by Albert McPhail in 1927. After the Star moved to Ouellette Street the property was turned over to the University of Windsor which redeveloped it while saving the historic facades.


St. Clair College Centre for the Arts
201 Riverside Drive West

Francis Cleary was born in County Fermanah, Ireland in 1840 but was on a ship for Montreal before he could walk. He was educated in Toronto and hung out a law shingle in Windsor; in the 1880s he won three consecutive terms as mayor. The Cleary family remained influential in Windsor affairs and in the 1950s E.A. Cleary donated $600,000 to the City for the construction of Cleary International Centre in memory of Francis and the men and women of the Windsor area who gave their lives in World War I, World War II and the Korean War. Johnson and McWhinnie, a leading mid-20th century Windsor architectural firm, drew up the plans. Among their other projects were the Windsor Public Library, the Windsor Yacht Club and Cody Hall at the University of Windsor. The City sold the property for $1 to St. Clair College in 2007 and the original building was transformed with a glass facade befitting its perch above the Detroit River. In addition to event space the St. Clair College Centre for the Arts includes the 1,200-seat Chrysler Theatre, home of the windsor Symphony Orchestra.  

Dieppe Gardens
78 Riverside Drive West at Ferry Street
In 1877 the Detroit Ferry Company and the Windsor Ferry Company dropped gloves and consolidated operations. The new passenger shuttle feature four steamships, all built within the decade. This is where the docks on the Canadian side of the Detroit and Windsor Ferry Company were located for decades. After World War II the docks were cleared and gardens created to remember the Essex Scottish Regiment of Windsor. The regiment was part of an invasion force that landed on the north coast of France on August 19, 1942 to raid the German-occupied port of Dieppe. The assault consisted of 6,086 men, 5,000 of whom were Canadians. Nothing went right on the beaches and 3,367 men were killed, wounded or captured.