13. Walking Conversations.

Sometimes you get caught up in city life, and the city starts feeling small, a bit mundane, and isolating. You forget that there’s millions of other people having completely different experiences than you. Which is the reason I live in the city, right? That’s the most exciting part of living in the city, is that you have all these stories happening right next to you.

On this episode, we look at a topic close to my heart: walking in groups, with friends or strangers. Going on walks around Toronto is how I got to know the city and how I met many of my friends, including Dylan, whose love of walking led him to co-found an advocacy group that works to make the sidewalks safer for pedestrians. Juan is on the Toronto organizing team for this year’s Jane’s Walk festival, the Jane Jacobs-inspired event where ordinary people across Toronto, and in many cities globally, lead “walking conversations”. We talk about what makes walking a great way to socialize (for introverts and extroverts alike), how exploring your city can make you more aware of its history and of the other lives going on all around you, and how anyone can lead a Jane’s Walk, get involved in pedestrian advocacy—or just round up some friends and start wandering.


Dylan Reid is one of the founders of Spacing, a magazine about Toronto's urban landscape; he’s Spacing's book series editor and the author of the Toronto Public Etiquette Guide. He is also one of the founders of Walk Toronto, a grassroots advocacy group. He has a Master's degree in history and is a fellow at the Centre for Reformation and Renaissance Studies at the University of Toronto.

Juan Gonzalez-Calcaneo’s first passion was filmmaking; studying film was the reason he initially came to Toronto from his native Mexico in the early aughts. Since then, Juan has focused on developing engaging communications strategies for important non-profits arts organizations and festivals in Toronto, leading him to open his own boutique communications agency. Juan’s dynamic career also includes a successful four-year run as a panelist on a hit MTV show breaking down stigmas attached to the LGBTQ community. He continues to advocate for and promote the arts and other causes he’s passionate about, leading him to become a Jane’s Walk Toronto 2019 City Organizer.

Show Notes.

Slouching towards Bethlehem by Joan Didion.

50 Toronto Hidden Gems & Curiosities, edited by Dylan Reid and Matthew Blackett.

Nyctophilia, a public art installation on Weston Road.


Trampoline Hall.

Jane’s Walk (Facebook, Twitter, Instagram).

Jane’s Walk in Toronto (Facebook, Twitter, Instagram).

Internet Mysticism in Wychwood Park.

Queer East.

The leather bar was mentioned in an episode of This Is Your Mixtape.

Walk Toronto (Facebook, Twitter).

Some background on Toronto’s buried rivers.

Toronto Company of Flâneurs and Flâneuses on Facebook.

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