I have really grown to love Toronto. No doubt I wouldn’t feel the same if I actually lived here, but for an impromptu break every so often, it is perfect. The city is unassuming, welcoming, and full of interesting people. It is also considerably less conservative than most of Western Canada.

More than anything in Toronto, I relish the chance to feel anonymous, but also bold. I have now lived in Regina for longer than I’ve ever lived anywhere before. I do love the sleepy, flat prairie city, and I could not have asked for a better place to raise our kids. I know I would not have been able to grow my small businesses in quite the same way anywhere else. Regina is also small enough that it is easy to become famous — or at least, notorious. Everyone knows each other within certain communities in Regina. The literary and bookish community is small but infinitely supportive. The queer community is even smaller, and the overlap between the two is considerable.

In terms of business, this is sometimes useful. For instance, I rarely have to spend money on advertising. But personally, it is another matter. This ‘fame’ that comes from being the owner of the only mainstream bookstore in town provides welcome ego-boosts at times of need, but it also fills me with fear. If I fail — which I am doing now both in business and in life in general — then everybody knows. There is no hiding place in the fishbowl, and unlike fish, Regina residents’ memory is longer than six seconds. I closed my coffee shop venture in 2017 due to monumental failure. To this day, people still refer to me as ‘Dr. Coffee.’ People remember your screw ups in Regina. Forever.

But in Toronto, I am no one.

At the same time, I am also anyone I want to be, without expectations and with fewer inhibitions. I love it.

One Sunday morning, I decided to embrace my no one/anyone big city identity. I donned my favourite purple and green jumpsuit, screwed my hair up into 1990s ‘space buns’ on top of my head, and took the streetcar to Church Street to the ‘Drag Brunch’ at Glad Day Bookshop. It was fabulous and exactly what I needed. The area just east of Yonge Street and running north towards Rosedale is Toronto’s gay village neighbourhood. I had just caught the tail end of Pride month, too. Rainbows were everywhere. I was pleased to see I was not the most colourfully-dressed person wandering up Church Street that morning, although someone did stop me to ask where I’d bought my jumpsuit.

Glad Day Books is the oldest queer bookstore in the world. It prides itself on being an inclusive, safe space, and an alternative to the plentiful gay bars that fill the same area. Here was somewhere where you could congregate in a supportive environment without the space being dominated by alcohol consumption, as welcoming on a Tuesday afternoon as on a Saturday night. It wasn’t hard to find, even amongst all the other Pride flags. Its large window showed the place already half full of excited people, most of whom were busy with brunch rather than browsing books. As I was alone, I was seated at the bar, and even my coffee arrived in a cocktail glass. A substantial brunch soon followed that I enthusiastically washed down with mimosas. Alcohol may have been optional, but it was an option I was happy to take!

As could be expected, it was a diverse audience. The host singled me out as the sole Brit in the building, but I was not the only person who’d never been to a drag show before. I met a lovely woman named Katie from the Maritimes, who was chaperoning a fourteen-year-old aspiring drag artist. She invited me to join them at their table so I’d get a better view. When the show started, a Lebanese drag queen (with a full beard) lip-synced songs in Arabic to raise money for Palestine, then managed to do the splits on the bookstore counter in thigh high heeled boots. We all threw our five dollar bills at her enthusiastically as tips. It was raucous, ridiculous, and absolutely the best thing that I could have spent Sunday morning doing. It was completely unlike anything that ever happens in Regina.

With the noise and mimosas and the party atmosphere of the drag show, it was easy to forget that this was a bookstore first and foremost. Books – mainly modern, queer nonfiction – lined the walls on all sides. Katie and I made some time to browse before she left. She asked me if I recommended anywhere else they should visit, as they knew Toronto even less well than I did. I suggested Little Ghosts horror bookstore, and the teenager’s face lit up at the idea.

This gave me a good excuse to talk to the lone bookseller about Glad Day itself. I had heard a little of their troubles before visiting. This was a bookstore where community support had been absolutely crucial to its survival. In the spring of 2024, after fifty-five years in business, Glad Day Books was facing eviction from its Church Street home. Their story sounded similar to mine: years of debts racking up, compounded by the pandemic lockdowns. This being Toronto, however, my substantial rent payment in Regina pales in comparison to the overheads that Glad Day were facing. So, they had taken the only option available to them: asking their community for help.

It worked.

True to form, it worked fabulously. The owner reported receiving over a thousand donations in the first 24 hours and raising $85,000 within the first few days alone. It was enough to secure their lease and carry on at least for the foreseeable future. This was a bookstore that was getting it right. Glad Day know who their customers are and are deeply entwined with the local neighbourhood. Their books, their events and their general appeal meant that even in a city the size of Toronto, it’s possible to create a sense of belonging in a close-knit community, and that community will value its bookstore and support it through the tough times.

Annabel Townsend is a book lover, coffee enthusiast, and optimistic entrepreneur in Regina, Saskatchewan. From 2020 to 2024, she was the owner of Regina’s The Penny University Bookstore, the first general interest independent bookstore to operate in the city for a decade.

Excerpted from Books and the City: Psychogeographical Wanderings Around Toronto’s Independent Bookstores by Annabel Townsend. Copyright © 2025 (Pete’s Press, Regina). Reprinted with permission. All rights reserved. The book publishes on Feb. 17 and will launch in Toronto on Feb. 19.