We’ve already covered that there’s a Toronto for every traveler, but what is it about Toronto that really makes it stand out from other Canadian and North American cities? Like other cities we’ve come to love, it’s incredibly multi-cultural and constantly growing. But if there’s anything that sheer size and activity lead to in a place like Toronto, besides a proliferation of businesspeople, skyscrapers, and suits, it’s unusual stuff.

After all, there has to be another side that makes a city stand out. At a glance, Toronto might resemble Chicago or even New York, but we know that these are obviously different places. Or, at least, you’re about to.

Unusual red holographic text appears on a wall above street artists and a crowd of bystanders in Toronto.
Photo by Alex Ortega

The Houses: Half, Little, and Doll

Particularly good for a unique Instagram shot, this trifecta of aesthetic and architectural weirdness forms a kind of triangle across Toronto. Besides their strange looks, these oddities offer the chance to explore different neighborhoods of the city and get away from the downtown area. They also each have a small story to tell, for those amongst us keen for curiosities.

The Half House is the only one amongst these that is centrally located, which adds to its intriguing appearance a charming degree of awkwardness — it’s just a stone’s throw from the U.S. consulate and a Japanese restaurant. It’s also architecturally frozen in time, an example of Toronto’s old bay-and-gable houses that sprung up during a 19th century revival of Victorian and Gothic styles.

The Little House is the littlest in Toronto, and probably the littlest functional bay-and-gable house you’ve ever seen — how little, exactly? Only seven feet wide. It was built in 1912, for no other reason than to satisfy the contractor’s curiosity. Arthur Weeden built and lived in this house, situated on a lot no wider than a driveway, for twenty-six years. It’s located close to the Corso Italia neighborhood, Toronto’s other Italian community (Little Italy being the first) that’s also home to authentic Portuguese eats.

Last but not least, the Leslieville Doll House is located in a sleepy neighborhood stretching along the shoreline, although you might not want to visit right before trying to sleep yourself (flashbacks to Chucky, anyone?) The colorful and crowded facade and front yard are simply the result of homeowner Shirley’s collecting hobby, and whether you consider this attraction funny or nightmare fuel, one has to admire her dedication.

Gibraltar Point and The Islands

It’s not “unusual” for a lighthouse to exist on a major body of water, but they are fascinating links to our past — especially when they’re as old as the Gibraltar Point Lighthouse and, of course, haunted. The story goes that its first keeper, JP Rademueller, was murdered in a drunken row with two soldiers from nearby Fort York.The tale is mostly used to spook schoolchildren and sneak in a history lesson at the same time, but checking out the light is just one among several great reasons to get out to the Toronto Islands.

A view of downtown Toronto from the central island ferry.
Photo by Alex Ortega

Take the ferry from the terminal at the foot of Bay Street for the added bonus of a great panoramic view of downtown Toronto on your way to a day on the Island, which you can spend any number of unusual ways. Take some friends out and rent a tandem bike, play disc golf, rent a kayak or canoe, test your balance on a stand up paddleboard, or have a picnic by the haunted lighthouse.

Centre Island also features a petting zoo and some stunning Japanese cherry trees, which are a must-see in late April/early May. There are also sand dunes to visit on the beach at Hanlan’s Point, and Olympic Island is said to have the very best view of Toronto.

EdgeWalk

At the opposite end of the adrenaline spectrum from tandem bikes and petting zoos is EdgeWalk, an experience that any thrill-seeker coming to Toronto cannot afford to miss. The CN Tower is the tallest building in Toronto, as well as the tallest anywhere in Canada and the 9th-tallest free-standing structure in the entire world. The best part about all that? You can walk around, outside, about half way up it: 116 storeys off the ground, in other words.

A profile shot of Toronto's CN Tower from below.

EdgeWalk was the first attraction of its kind in North America, has the designation of a Canadian “Signature Experience,” and is still the world’s highest circular walk. Your mission, should you choose to accept it, involves walking with a group of five other visitors on a ledge only five feet wide that  leans out over the Toronto skyline. It’s closed during the winter, but will operate in any kind of safe weather during the rest of the year. They even advertise the appeal of varying weather conditions for a more ‘unique’ experience. Radical.

Try Paan and Indian Sweets on in Little India

The Gerrard India Bazaar is one of the biggest South Asian marketplaces in North America, but there is more to Little India than just curry houses and exotic clothing stores. There are treats available here you won’t find in many places outside of India itself, like confectionaries and authentic soft drinks, but the most unusual and acquired taste among them is Paan — a chewed snack made by wrapping areca nut and other ingredients in a Betel leaf. The combination creates a relatively mild psychoactive effect, comparable to coffee and tobacco.

An unusual and exotic dish at a Toronto restaurant.
Photo by Alex Ortega

You can find Paan elsewhere in North America, but it’s more accessible to first-timers here in the Bazaar, where it’s often served with sweeter ingredients in place of actual tobacco. It does depend on who you ask, and who’s making it, because partaking in Paan can be a sweet after-meal treat or associated with groups of old men sitting around for hours at a time, as with shisha in Middle Eastern and North African cultures. It’s not for everyone, but if you’re looking for something new and unusual, try it with honey at Baldev Paan. If not, stick with the fruity and fizzy drinks they serve, like Maaza and Limca.

Casa Loma

A building project so overly ambitious that it bankrupted its owner and financier in less than ten years through tax costs alone, Casa Loma is to opulence as EdgeWalk is to thrill-seeking. 20th-century energy mogul Henry Pellatt, responsible for bringing the first widely available electricity to Toronto, decided to build this 98-room chateau after amassing enough wealth to rival the European castles that inspired him in his youth, though there’s doubt he saw any that featured three bowling alleys, two pipe organs, or an oven large enough to cook an ox.

The interior of Casa Loma in Toronto.

The city repossessed the property in the mid-1920s and it stood abandoned for about a decade until a reporter, who was initially sent to investigate paranormal activity, instead decided to make a public appeal to save it from demolition. It was then, in the late 30s, that the building’s long and illustrious history as a tourist attraction began. Today, you can explore every inch of the lavish and ornate interior, as well as the gardens and stables which currently house an exhibit on vintage automobiles. If the lighthouse ghost story wasn’t enough of the supernatural for you, investigate the claims from the 30s by taking a ghost tour through Casa Loma.

Kensington Market

The Market” has become much more than what the name implies, evolving from a traditional market into an entire neighborhood that embodies the same eclectic spirit. The lively and diverse range of people who work here and make it their home do justice to what is now a legendary name in Toronto and the whole of Canada. It blends and combines with nearby Chinatown to form the city’s most vibrant collection of sights, tastes, and sounds that easily rivals London’s Brick Lane and Brooklyn’s flea markets.

A unusual graffiti-covered street corner in Toronto
Photo by Alex Ortega

Kensington is the kind of place where, in the same afternoon, you can eat dim sum, drink mezcal, try on vintage clothes or a Grinch costume, and watch a skateboarding Spider-man named “Peter Parkour” perform down the street from a mural influenced by Czech nouveau art. The Market caters to so many different tastes, from thrift shops and cheap eats to curated denim stores and fine dining, that it’s perfectly possible to just turn up and go where your fancy takes you. If you’re looking for a more organized experience, hop on a food tour or check out the neighborhood on a Sunday, when there’s an art fair and DJ sets at a couple of bars.

Whether you’re an adrenaline junkie, ghost hunter, bizarre foodie, or just someone with a special appreciation for the offbeat in life, Toronto has got you covered. And if you’re looking for more activities along these lines, be sure to check our Alternative Shopping Guide while you’re at it!

The Marriott International portfolio of hotels in iconic neighborhoods across the Greater Toronto Area promise to be the perfect hosts for your next visit. Iconic brands like Westin, Sheraton and Delta are joined by Canada’s first St. Regis hotel and the world’s richest travel program, Marriott Bonvoy. Enjoy member exclusive rates and experiences when you book direct at marriott.com.

Header photo by Alex Ortega.

Share this:
Joseph Ozment
Originally from Tennessee, Joseph Ozment is a writer and musician whose relationship with travel was shaped by growing up between the Southern U.S., Wales, and Hong Kong. So far, he's written for a newspaper in Russia, released a handful of home recordings, and started a novel (with plans for more, someday). When he's not busy running country roads or cheering on Liverpool FC, he's most likely making the next cup of coffee, or plans for the next trip.