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Distillery District millers William Gooderham and James Worts established one of Toronto's first waterfront industries here in 1832; its windmill became a landmark in the young town. The site operated – including through Prohibition – until 1990; a decade later it began its second life as a retail, cultural, and residential neighbourhood, a likely precedent for 21st-century downtowns.

At the moment, it feels slightly Disneyfied, but the brawn and patina of the architecture give the place some soul.

1. The Stone Distillery

2 Trinity St.
David Roberts Sr.
Renovated in 1870 after a fire
Renovation, ERA, 2003

The oldest surviving building in the Distillery, this once faced the wharves where materials and products came and went. A fire in 1869 did not touch its outer walls, and distillery employees soon rebuilt it; production continued here until 1957. Today the brawn of the building's wood structure and stone walls serve as atmospheric backdrops for creative-class professionals. Interpretive panels and exhibits in the stairwell explain the distillery processes.

2. Fire Pump House

South end of Trinity St.
David Roberts Jr.
Renovation, ERA, 2002

The last building added here in the Victorian era, this has lost most of its tall chimney but retains much of its deliciously elaborate brickwork.

3. Pure Spirits

15 Trinity St.
David Roberts Jr.

The fine glassy facade at 15 Trinity had a very serious practical intent: the front of the building housed stills, and any explosion would dissipate its energy out the windows. The fact that William Gooderham could see this facade from his office may have inspired a certain level of quality. Today that volume is handsome office space (all private) and retail at ground level.

4. Pure Spirit, Clear Spirit, and The Gooderham

70 Distillery Lane.
2008 and 2013

Three crisp Neo-Modernist glass towers – the latter two, at the east end, enlivened by variegated and kinked balconies – rise in contemporary counterpoint to the Distillery District. The bases, with their cladding of long red bricks and punched windows, engage with the 19th-century form and materiality. (A set of canted concrete columns on the east side of Clear Spirit hit the ground with poetic force.)

5. Young Centre

50 Tank House Lane
David Roberts Jr.
1883 and 1888
Renovation, KPMB, 2006

The two tank houses, built for the storage and aging of spirits, feature solid massing and intricate brickwork; their open volumes have lent themselves well to theatre uses. The renovation shows the hand of KPMB's Thomas Payne, channelling Louis Kahn in the deep doorway details and hefty oak benches around the lobby hearth.

6. Canary District and Canary Park (condominium apartments)

398 Front St. E. and 120 Bayview Ave.

Curved buildings are rare in Toronto, but this pair of towers responds sinuously to their park-front site. A tailored facade of ironspot brick and glass is capped with Aalto-esque curved penthouses; with elegant townhouses at ground level and a through lobby, this is sensitive urbanism.

7. Canary District, precinct plan and block plans

Cherry and Mill streets
Urban Design Associates and du Toit Allsopp Hillier
Public realm and urban design
The Planning Partnership and Phillips Farevaag Smallenberg

A rare master-planned neighbourhood in Toronto, this district was expropriated in 1987

for an affordable-housing scheme that came to be called Ataratiri; then the land sat fallow for nearly 20 years before being rebuilt in a hurry to serve as the athletes' village for the 2015 Pan Am and Parapan Am Games. A Canadian dream team of architects and planners assembled a coherent mid-rise district that expresses the best of architecture and urbanism of its period: walkable, tightly detailed, formally coherent, and very grey. A consistent, six-metre ground floor creates strong retail and public spaces, while the public realm includes wide sidewalks with granite curbs. The plaza along the north side of Front Street (positioned to catch sunlight) includes two fine works of public art, Tadashi Kawamata's Untitled (Toronto Lamp Posts) and The Water Guardians by Jennifer Marman and Daniel Borins.

8. Cooper Koo Family Cherry Street YMCA/George Brown College Student Residence

461 Cherry St.
MacLennan Jaunkalns Miller and architectsAlliance

A complex and urbane ensemble, capped by a 500-bed student residence and ringed by sophisticated public space. The Y's interior is rational, tightly organized, and beautifully daylit, typical of the deeply competent MJM. The Cherry Street facade is marked by a bold red protrusion full of angled screens for sunshading; on Front Street, aA's irregular cluster of columns forms a dynamic composition while supporting the mass of the residence above.

Excerpted from Toronto Architecture: A City Guide by Patricia McHugh and Alex Bozikovic. Copyright 2017 by the Estate of Patricia McHugh and Alex Bozikovic. Published by McClelland & Stewart, a division of Penguin Random House Canada Ltd. Reproduced by arrangement with the publisher. All rights reserved.