Old City Hall Cenotaph, Toronto

The Old City Hall is a Romanesque-style civic building and former court house in Toronto, Ontario, Canada. It was the home of the Toronto City Council from 1899 to 1966 and a provincial court house until 2023, and remains one of the city's most prominent structures. The building is located at the corner of Queen and Bay Streets, across Bay Street from Nathan Phillips Square and the present City Hall in Downtown Toronto. The heritage landmark has a distinctive clock tower which heads the length of Bay Street from Front Street to Queen Street as a terminating vista. Old City Hall was designated a National Historic Site in 1984.

The Battle of York was a War of 1812 battle fought in York, Upper Canada (today's Toronto, Ontario, Canada) on April 27, 1813. An American force, supported by a naval flotilla, landed on the western lakeshore and captured the provincial capital after defeating an outnumbered force of regulars, militia and Ojibwe natives under the command of Major General Roger Hale Sheaffe, the Lieutenant Governor of Upper Canada. After Sheaffe's forces were defeated, he ordered his surviving regulars to withdraw to Kingston, abandoning the militia and civilians. The Americans captured the fort, town, and dockyard. They themselves suffered casualties, including force leader Brigadier General Zebulon Pike and others killed when the retreating British blew up the fort's magazine. After the American forces carried out several acts of arson and looting, they seized ordnances and supplies from the settlement and subsequently withdrew from the town weeks later. Although the Americans won a clear victory, the battle did not have decisive strategic results as York was a less important objective in military terms than Kingston, where the British armed vessels on Lake Ontario were based.

Old Toronto is the part of Toronto, Ontario, Canada, that corresponds to the boundaries of the City of Toronto prior to 1998. It was incorporated as a city in 1834, after being known as the town of York, and being part of York County. Toronto periodically grew in size by annexing adjacent land and municipalities. In 1954, the City of Toronto and the surrounding suburban towns and townships of York County were joined in a federation known as the Municipality of Metropolitan Toronto (Metro). Later, the lower-tier city annexed two towns until it reached its final boundaries in 1967. In 1998, the municipalities of Metro Toronto were amalgamated into the present-day single-tier City of Toronto, which continues legally from the predecessor City of Toronto, although the by-laws of each municipality remained in force. Historically, "Old Toronto" referred to Toronto's boundaries before the Great Toronto Fire of 1904, when most urban development was to the east of Yonge Street. Since the 1998 amalgamation, however, the 1967–1998 area of the lower-tier city is referred to as "Old Toronto" or the "former city of Toronto". It is sometimes less accurately referred to as "downtown" (Downtown Toronto is located within Old Toronto) or as "the core". Old Toronto has a population density of approximately 8,210 residents per square kilometre, which would rank as Canada’s densest (North America's second-densest) city with a population over 100,000 if it were still a distinct city.

York was a town and the second capital of the colony of Upper Canada. It is the predecessor to the old city of Toronto (1834–1998). It was established in 1793 by Lieutenant-Governor John Graves Simcoe as a "temporary" location for the capital of Upper Canada, while he made plans to build a capital near today's London, Ontario. Simcoe renamed the location York after Prince Frederick, Duke of York and Albany, George III's second son. Simcoe gave up his plan to build a capital at London, and York became the permanent capital of Upper Canada on February 1, 1796. That year Simcoe returned to Britain and was temporarily replaced by Peter Russell. The original townsite was a compact ten blocks near the mouth of the Don River and a garrison was built at the channel to Toronto Harbour. Government buildings and a law court were established. Yonge Street was built, connecting York to the Holland River to the north. To the east, Kingston Road was built to the mouth of the Trent River. In 1797, the town site was expanded to the west to allow for public buildings and expansion. One of the new area's public functions, a public market, was started in 1803. It continues today as St. Lawrence Market. The settlement was attacked by American troops during the War of 1812. As the British garrison retreated, they detonated their powder magazine, inflicting numerous casualties on the invading U.S. forces, who proceeded to loot and destroy the town. The victorious Americans chose not to occupy the town and the British eventually returned without conflict. A reprisal attack was made on the American capital of Washington, D.C. a year later. After the war was over, the town continued to grow, expanding to the west, leaving the original town site, a less desirable location, somewhat undeveloped. A new parliament building was erected, near the original location, but this burned down and a new building was built in the new lands to the west. A permanent fort, Fort York, was built on the site of the garrison. Dundas Street was built to connect York to towns to the west. In the 1820s, the town experienced a surge of immigrants, expanding from 1,000 residents to over 9,000 by the time the town was incorporated as the City of Toronto in 1834. During its existence, the town did not have its own government; it was governed by the province of Upper Canada, with a mix of elected officials and an aristocracy known as the Family Compact controlling the government. By 1830, this led to an ongoing political conflict, which would later lead to the 1837 Upper Canada Rebellion.

The Simpson Tower, located at 401 Bay Street, is the 38th-tallest building in Toronto, Ontario, Canada. Completed in 1968 by architect John B. Parkin, as the headquarters of the Simpsons department store company, it has 33 floors and is 144 m (472 ft) high. In 1978, as part of a corporate takeover, the Simpson Tower became the property of the Hudson's Bay Company. The building today remains the head office of HBC and also houses the head office of subsidiaries Hudson's Bay and Home Outfitters. It is adjacent to the historic Simpsons store at Yonge and Queen, which includes Arcadian Court. Today the store is the flagship for Hudson's Bay, is integrated with the Eaton Centre across Queen Street, and is the home of Toronto's comprehensive health centre. In January 2014, Hudson's Bay Company announced it would sell the tower and adjacent store to Cadillac Fairview and lease the site for 25 years.

The Temple Building was a 12-storey, 36.93 m (121.2 ft) highrise erected at 62 Richmond Street West and Bay Street in Toronto, Ontario.

Shea's Hippodrome was a historic film and play theatre in Toronto, Ontario, Canada. The Hippodrome was located in downtown Toronto, at the southwest corner of Albert and Bay streets (now Nathan Phillips Square). At its opening in 1914, it was the largest movie palace in Canada, and one of the largest vaudeville theatres in the world. The Hippodrome included 12 opera boxes, a Wurlitzer organ, as well as a full-size orchestra pit. It debuted some of Canada's first non-silent films. It was built by brothers Jerry and Michael Shea and situated directly across from Toronto's (now former) City Hall. The Hippodrome was operated by Famous Players and managed for decades by Leonard N. Bishop. It was demolished in 1957 to make way for Toronto's new City Hall.

The Broadway Theatre was a burlesque live theatre and cinema in Toronto, Ontario, Canada. The theatre was opened under the name of Globe Theatre, in 1918. It was renamed the Roxy Theatre in the early 1930s and assumed its final name, the Broadway Theatre, in 1937. It was located on the southwest corner of Bay and Queen streets at 75 Queen Street West. The Broadway was initially a traditional Burlesque theatre. In 1933, it was renamed the Roxy and offered girlie shows. In 1935, the theatre's manager was murdered in his office. $378 appeared to have been stolen, but, according to author and cinema historian Doug Taylor, Toronto Police did not believe robbery was the motive. The shooter was never identified. Taylor wrote that when New City Hall was to be built on the north side of the street, politicians felt that the Broadway and the Casino Theatre, another Burlesque theatre just five doors west, pawn shops and the block's other businesses were inconsistent with civic dignity, and the whole block was expropriated and demolished in 1965. Following a two year construction, from fall 1972, the block became the site of the large Four Seasons Sheraton Hotel (since rebranded as Sheraton Centre Toronto Hotel). At the far corner was an office block with a Toronto Dominion Bank branch, which was also demolished and replaced with a low rise glass pavilion housing a TD Bank.

Sterling Tower is a twenty one storey art deco skyscraper at 372 Bay Street at Richmond Street in Toronto, Ontario, Canada.

The Arcadian Court is an Art Deco event space in Toronto, Ontario, Canada. It is located on the eighth floor of the flagship downtown Toronto location of the Canadian department store The Bay at Yonge and Queen Streets. For many years, it was an exclusive restaurant, then an art gallery, then closed and used for storage. It was restored and is now used as an event space. The facility first opened in 1929, when the store was part of the Simpson's chain. The Arcadian Court was intended to compete with the Royal York Hotel's Imperial Room, the Georgian Room at the main Eaton's store, and the Eaton's Seventh Floor on College Street (now called The Carlu) for downtown lunch business. The Court was two stories in height, the main floor and a mezzanine (called "The Men's Grill" from 1968–1969), which was men-only for many years. The restaurant's architecture featured wrought iron railings, arched windows, and huge chandeliers. Three skylights allow light to enter the whitewash hall interior. At its opening, it was the largest department store restaurant in the world, seating 1,300. The restaurant hosted many of the Toronto Symphony Orchestra's first radio broadcasts, and in 1967, it hosted the first auction ever held outside Britain by Sotheby's. In 1978, Simpson's was acquired by the Hudson's Bay Company, and subsequently became downtown Toronto's flagship Bay store in 1991. From 1988 to 1989, some of the mezzanine space was converted to gallery space, which displayed the Canadian art collection of Kenneth Thomson. Much of the second floor of the Arcadian Court was closed off or used for the storage of chairs. A small pictorial display and a cast-iron fountain is located outside the hall. This gallery space was closed in 2004, and the Thomson collection was transferred to the Art Gallery of Ontario and now displayed as the Thomson Collection. Reopened in May 2012, the Arcadian Court is now a part of a larger event complex (which now includes the neighboring Arcadian Loft) called "Arcadian", which is operated by Oliver & Bonacini Events. The renovations were carried out by architecture firm DeSignum Design. The renovations have stripped back layers of walls and flooring that have been added over the years, reclaiming approximately 5 feet (1.5 m) of the perimeter. The arches were also restored. Eight of the 16 grand arches in the mezzanine that were closed off in past renovations were reopened and the squared-off arches were restored. The renovations added 4 feet (1.2 m) in height to the remaining eight. The Court is now 8,086 square feet (751.2 m2) with improved acoustics, new chandeliers that are a deconstructed take on the original Lalique crystal chandeliers and an opened-up mezzanine. The "Arcadian Court" name has been carried on as a brand name for other restaurants operated in Bay stores, though none are as opulent or exclusive as the Toronto original was. The Arcadian Court also figures prominently in Margaret Atwood's novel The Blind Assassin, as the center of Toronto's high society to which Iris Chase Griffen is introduced.

Bell Trinity Square is an office complex occupying part of the former site of the historic Eaton's Annex in downtown Toronto, Ontario, Canada. The name is a combination of: the name of original and now former occupant Bell Canada; the location of the site south of the Church of the Holy Trinity; and Trinity Square. Built in from 1980 to 1983 and designed by architect John B. Parkin, the post modern complex consists of 15 floor and 10 floor towers connected by a glass atrium. The building is connected to the Toronto PATH underground pedestrian network. After renovations completed in 2010 which brought the building up to LEED Gold standards, the first retrofitted building in Toronto to achieve the standard, the site has been partially used by CIBC.

The Economic Club of Canada is a non-partisan speaker’s forum based in Canada, and modelled on American societies such as the Economic Club of New York, or the Economic Club of Pittsburgh, although the latter organizations are not-for-profit. The Canadian organization meets three times a week and provides a platform for policy makers and business leaders. Notable former speakers have included John Tory, Bill Clinton, Kathleen Wynne, Mike Savage and John McCallum. It markets itself as a business elite organization that can turn events around quickly, thus making its events more timely and newsworthy. Members are drawn from the business, industry and finance sectors. Speeches are typically held in the modern hotels in various cities over the lunch hour. Tickets to the events can be individually sold or by table to the companies, organizations or private members.