Walking tour of Toronto's Annex: the KESKUS neighbourhood

Join your host Christina Prozes on a walking tour of one of Toronto's historic and distinctive neighbourhoods, one that is deemed a Top 40 Coolest Neighbourhoods in the World by Time Out Magazine and where Estonian architects have made their. Welcome to the Annex !

The Annex burst to life in the late 1880s as Toronto's premier high Victorian playground, where flamboyant railroad barons, merchant kings, and eccentric tycoons built a mix of massive, theatrical red-brick mansions. Designed to flaunt immense wealth with aggressive turrets, Romanesque arches, and stone gargoyles, it was a hyper-exclusive enclave that brazenly redefined the city's architectural skyline.

And then came the Estonians - while traditionalists of the 1960s scoffed at anything that wasn't a standard brick box, Estonian architect Uno Prii used a special slip-form pouring method to create poetic, fluid, sculptural towers inspired by the American space race and European modernism. His bold, expressive style gave dignified, artistic housing to the dense, growing student and immigrant population of the Annex. Of the some 250 buildings by Uno Prii in Toronto, 34 of his finest buildings are here in the Annex and are fiercely guarded heritage gems.

Buried rivers, the massive tree canopies of Toronto's primeval forest from before the city grid and lots more lore! In English with consecutive translation by KESKfEST Youth Delegates.

Christina Prozes

Christina Prozes is a cultural advocate based in Toronto, with deep roots in the Estonian-Canadian community. Re-wired from a career with the Ontario government, Christina is passionate about local history, urban nature, and architectural heritage, she designs and conducts engaging walking tours that explore Toronto’s rich neighborhood narratives. Her tours seamlessly blend the city’s activist past, hidden historic gems, and the unique contributions of immigrant communities—such as the post-war Estonian architectural wave—offering participants an insightful, story-driven journey through Toronto’s evolving urban landscape.

Our route:

We'll meet at the northwest corner of Dupont & Spadina take a peek from afar at Casa Loma, one of Toronto's top tourist attractions, before wending our way back toward KESKUS, passing by several Uno Prii designed buildings, and end up back at KESKUS and Elmar Tampõld designed Tartu College!

To get to Dupont Station, either one stop northbound from Spadina subway, or walk the approx. 1km from KESKUS.