There are endless possibilities for walking tours in Toronto and, with so many neighborhoods marked by their own history and presence, it’s hard to know where to start. However, two definite must-see areas are the entertainment and financial districts, and the Old Town of York.

To get a sense of Toronto’s entertainment district, start at the corner of King and John. This area (stretching to Simcoe) is known as Mirvish Walkway or Mirvish Village, named after Ed Mirvish and his son, who have spent awesome amounts refurbishing the area, turning many of the theatres and restaurants into first-class establishments. Their most famous project, the Royal Alexandra Theatre, was saved from certain destruction and has become one of the city’s entertainment jewels.

Just down and across the street, there’s no missing the grand exterior of Roy Thomson Hall, with its glass and upside-down mushroom shape. The interior of this performance hall, a favorite venue for the Toronto Symphony and Mendelssohn Choir, is just as spectacular: luminous and elaborate décor topped by impeccable acoustics.

Head east and, on the corner of King and Simcoe, you’ll find St. Andrews Presbyterian Church. Constructed in 1876, the church was saved in the 1980’s when SunLife Tower paid over $4 million to build above and below it. The Scottish Romanesque Revival architecture stands in time-warp contrast to the skyscraping steel and glass around it.

Halfway between York and Bay you’ll pass the Standard Life Building, which stands beside the awesome Toronto Dominion Centre, consisting of five monolithic skyscrapers. The creation of famous modernist Ludwig Mies van der Rohe, the centerpiece building of the group, the Toronto Dominion Tower was the first International Style skyscraper in the city when built in the late 1960’s. The finished product was a meticulously constructed work of art that, while perhaps not visually stunning, set the tone for the architecture that followed.

Heading north on Bay you’ll come across the National Club Building, a Neo-Georgian structure built in 1874 to promote the Canada First movement patriots who fought to prevent union with the United States. Just up the street is the Canada Permanent Building, an historic site built in 1929. The Art Deco style along with the vaulted entrance and sculpted bronze elevator doors make the interior a must-see. Back up to King and further east stands the Canadian Imperial Bank of Commerce. When it was built in 1931, the 34-storey building was the tallest in the British Empire. Its Romanesque-Revival architecture, handsome wrought-iron detail and gilded moldings work well even in the contemporary backdrop of the city’s financial district.

Further west and right on Wellington can be found the old Commercial Bank of Midland District, now called Number Fifteen. The oldest structure in the area, it was built in 1845 in classic Greek Revival style. Down Bay and south to Front brings you to the old Toronto Stock Exchange, now the Design Exchange, which exhibits work from some of the world’s finest fashion and graphic designers.

On Front Street stands Union Station, completed in 1927 after 12 years of construction. The work of architects Ross and MacDonald, the building was modeled after the great U.S. railway stations and inspired by the basilicas of Ancient Rome. The massive, 250-metre long building sports magnificent columns, beautifully vaulted ceilings and ornate etchings in its stone walls.

If you’ve got some energy left after visiting the entertainment and financial districts, continue with a tour of the Old Town of York, where you’ll get a sense of Toronto’s rich history. Start at the corner of Yonge and Wellington and walk east to the Gooderham Building, financed by distilleries mogul George Gooderham and also known as the Flatiron Building due to its triangular structure.

Turning onto Front, the Beardmore Building stands out. During the 19th century, the area was known as the warehouse district, and this building was one of the first structures built to accommodate the busy waterfront industries. Further east to Jarvis, the historic St. Lawrence Market bustles more than ever with its fresh fruit, vegetable, cheese and meat vendors. Built in 1844, Toronto’s city hall stood here until 1904 when the space was converted into a public market. Since then it has been expanded, though the old city hall façade is still recognizable. Once home to working-class Irish Protestant immigrants employed in the many factories and warehouses surrounding it, the St. Lawrence Market area today is a trendy neighborhood, with a nice blend of old and new.

East on Front, you’ll find Trinity, a beautiful old street that features the Enoch Turner Schoolhouse, the oldest school building in the city and the first to offer free education. It was built in 1848 by Enoch Turner, a local brewer who employed many of the folks who lived in the area. A few steps south is Little Trinity Church, which was built for area Anglicans who couldn’t afford the steep pew rents at St. James Cathedral. While not as spectacular as the city’s other old churches, the simple Tudor Gothic styling gives it an almost magical appeal.

North to King, there’s no missing St. James Cathedral, Toronto’s first Anglican church, boasting the highest steeple in Canada and the second highest in North America. Built in 1819, the church was destroyed in a fire that devastated the entire city in 1849. It was rebuilt by architect Frederich Cumberland, who redid the exterior in Gothic Style.

Walk west and turn north on Toronto Street and you’ll notice a building with architecture resembling a Greek temple, complete with symmetrical Ionic columns. Occupied today by the Argus Corporation, it was once a customs office, a branch of the Bank of Canada and a Post Office.

Back on King, between Church and Leader Lane, comes the magnificent King Edward Hotel, designed by the same architect who oversaw the original City Hall and Massey Hall.

To finish off your tour, return to St. James Cathedral, walk through the Toronto Sculpture Garden, and you’ll find yourself at Market Square. Here you can relax in one of the many cafés, enjoying the bustle of Toronto’s oldest neighborhood.