Despite having grown up in Toronto, I surprisingly learned quite a bit about the city’s history on the Underground Donut Tour ($50 for children or $60 for adults). Over two hours, we leisurely covered around two kilometres around Queen Street West and Kensington Market, stopping at four vendors to sample their sweet treats. With roughly a doughnut’s worth of goodies per person at each stop, I’d recommend bringing a few friends so you can split everything and try more flavours without completely being knocked into a sugar coma.

The tour concept started in Chicago in 2015, when Jeff Woelker, a self-proclaimed doughnut fanatic, decided to share the Windy City’s doughnut scene with more people. He started leading tours himself, and the idea proved so popular that the company has since expanded to five countries, employing more than a hundred doughnut lovers.

Our tour was led by Rob, a prompt and friendly guide who had Sheldon Cooper’s encyclopedic knowledge of the city’s history and landmarks, paired with Leonard Hofstadter’s warmth and ability to put everyone at ease. Before long, we were chatting and sharing treats like old friends. If you’re confused by those references, I guess you don’t watch The Big Bang Theory.

Our first stop was Cops, a cheeky nod to the stereotype of police officers loving doughnuts. Here, we tried some of the freshest, airiest mini doughnuts I’ve ever had. The company worked with chefs to develop a light batter that makes these little treats stand out.

There are only three flavours to choose from: cinnamon sugar, O.G. sour cream, and a rotating weekly feature. With such a simple lineup, the focus is firmly on the dough itself. I loved the traditional cinnamon sugar, which brought back memories of Tiny Tom doughnuts at the CNE. But it was the featured alfajor that had us reaching for seconds. The fluffy fried dough was coated in caramel glaze and topped with toasted coconut and shortbread cookie crumbs. Dangerously delicious, these were the kind of doughnuts that made practising self-control feel like an actual chore. And we still had three more stops to go!

Thankfully, we had a chance to walk off at least a fraction of those calories before reaching the next bakery. We strolled through Graffiti Alley, where Rob shared the stories behind the colourful murals, including works by Toronto's own Uber 5000. I won't spoil all the fun by revealing everything we learned, but the alley is packed with vibrant street art worth taking the time to appreciate. Consider this a little preview of what you'll see along the way.

Our next stop was Bloomers, a well-known local bakery that's entirely vegan and offers gluten-free baked goods and savoury treats (though its doughnuts aren't gluten-free). If the word vegan immediately makes you think of bland, joyless baking, give Bloomers a chance. These doughnuts are flavourful and pillowy enough that you won't be sitting there wondering where the butter and lard went.

Apple fritters are among my favourite doughnuts, so I couldn't resist trying Bloomers' apple fritter. It had that familiar combination of cake-like and yeasty dough, studded with big chunks of apple and seasoned with well-balanced spices, all finished with a light glaze. While St. Jacob's Farmers' Market still takes the crown for my favourite apple fritters, Bloomers' version was a respectable contender.

We also tried a Ferrero Rocher doughnut, a limite- time fall flavour filled with custardy chocolate cream and covered in a thick, soft chocolate ganache. This was an indulgent, seriously rich treat. Delicious? Absolutely. But even with our sweet tooths in full swing, a quarter of a doughnut was enough to leave us satisfied.

Luckily, a stroll through the neighbourhood gave us a chance to admire the fall colours before arriving in Kensington Market for the final stretch. One of the potential stops is I Love Churros, a standalone outpost from Pancho's Bakery. The churros are made fresh to order, arriving piping hot with a crisp exterior and a light, airy centre. Honestly, freshly fried churros are hard to resist.

You can also have your Mexican churro filled with chocolate, dulce de leche, strawberry, or condensed milk. We sampled the condensed milk version, and I was pleasantly surprised that it wasn't overly sweet. Perhaps some of the milk had escaped into the bag, but what remained added just a hint of sweetness and a delicate glaze to the crunchy pastry.

By this point, we were getting pretty full, but one look at the display case at Dipped Doughnuts and all thoughts of restraint went out the window. Although an apple fritter was on offer, we opted for something more unusual: the mango mint jelly doughnut. This was easily one of the most distinctive bites of the day. The sweet fruitiness and slight tartness of the mango were balanced by a refreshing mint finish… bringing to mind a mash-up of mango chutney and a mojito. An unexpected combination, but one that worked brilliantly. It ended up being one of my favourite doughnuts of the entire tour.

Rob also swore by the brown butter sea salt doughnut, so naturally, we had to try it. He didn't steer us wrong. The brown butter aroma was intoxicating even before the first bite, and the sweet-savoury glaze added plenty of flavour without overpowering the yeasty brioche dough. Sometimes the simplest combinations are the most satisfying, and this was proof.

One of the nice things about the Underground Donut Tour is that the experience can change with the seasons, as bakeries introduce new and limited-time flavours. You can revisit the Toronto tour at different times of the year or explore the company's other tours in Canada, the UK, Ireland, and the US. There's always another excuse to eat doughnuts, right?

My friend and I both agreed that this isn't just a tour for visitors. Even if you've lived in Toronto your entire life, there's something fun about rediscovering familiar neighbourhoods while learning about their history, architecture, and local businesses.

It's also a great idea for a birthday outing with tweens or teenagers: they'll get plenty of sugar, lots of opportunities for social mediate-worthy content, and a chance to appreciate the city beyond their phone screens. Just bring friends to share the doughnuts, pace yourself, and don't make the mistake of eating a huge meal beforehand!