50 Ways to Fall in Love With Toronto All Over Again
Updated: Nov. 24, 2019
Whether you’re a seasoned Torontonian, new to the city, or a tourist touching down for a visit, these 50 things to see and do will convince you that Toronto the Good is actually really, really great.
1. The Toronto skyline
There are a handful of spots to catch a picture-perfect view of Toronto’s iconic skyline, but these three should top your list: the crest of the hill at Riverdale Park (grab a cocoa at Rooster Coffee House first), the west shore of Tommy Thompson Park (known locally as Leslie Street Spit) and the north shore of Toronto Island. You’re welcome, Instagrammers! #PerfectView.
2. CN Tower EdgeWalk
If you’ve already stood on the glass floor of the Wonder of the Modern World that is the CN Tower, it’s time to take the next challenge: The EdgeWalk. The adrenaline-pumping attraction takes participants around the exterior of the restaurant’s roof – a whopping 1,168 feet above the city streets.
3. Friday Night Jazz at Ripley’s Aquarium of Canada
On the second Friday of every month, Ripley’s Aquarium of Canada (home to 16,000 aquatic specimens) invites non-gilled guests to sip cocktails and enjoy some live jazz. Where else can you pet a stingray, sip a martini and tap your foot to a beat at (almost) the same time?
4. Toronto’s stories
Performance storytelling is one of Toronto’s hottest new scenes, and it provides the perfect opportunity to hear the sometimes sad, often hilarious and always true tales of the everyday people who populate the city. Take advantage of a packed calendar of monthly storytelling events, ranging from Dare (“stories you never thought you’d tell”) to High Stakes (“stories that that significantly changed you”). A particular favourite is Raconteurs, held on the second Wednesday of every month at the Tranzac Club. Go early, it fills up fast!
5. Doors Open Toronto
Doors Open Toronto, held on the last weekend in May, sees more than 150 buildings of cultural, historical or architectural importance open up to visitors for free. The roster changes each year, but past participants include the R.C. Harris Water Filtration Plant (the city’s largest water treatment plant, pictured here), a textile museum, the marine police station and a “lost” subway station.
6. Toronto Island on a tandem bike
Even though they’re only a short ferry ride from downtown, the Toronto Islands feel like an escape from city life. First settled as a leisure destination back in 1862, it’s best explored on a bicycle built for two.
7. Allan Gardens Conservatory
Curing the winter blues since 1910, Allan Gardens Conservatory is a glass-and-steel-domed greenhouse in the centre of the city. With exotic tropical plants and a collection of cacti, the jungle and the desert are just a few steps apart, 365 days a year.
8. High tea at the Windsor Arms Hotel
Redefine leisure over an elegant afternoon tea at the historic Windsor Arms Hotel. The traditional tea service-complete with sherry or sparkling wine, finger sandwiches, scones and exotic loose-leaf teas-will make you feel like royalty.
9. High Park’s cherry blossoms
Under a canopy of fluffy pale-pink blooms, breathe in the sweet scent of High Park’s cherry blossom trees, the first 50 of which were gifted to Toronto by Tokyo in 1959. These fleeting flowers are in bloom for less than two weeks between late April and early May, so track their progress on the High Park Nature Centre website before you visit.
10. The Distillery Historic District Christmas Market
From mid-November to late-December, a magical European-style Christmas market takes over Toronto’s historic Distillery District. With its cobblestone streets, 55-foot Christmas tree, costumed carollers, mulled wine and turkey drumsticks, the charmingly old-school celebration feels plucked from the pages of a fairy tale.
11. The Second City
It’s hard to ignore Canada’s contribution to the comedy scene when we can lay claim to some of the greats-many of whom spent their early years performing at Toronto’s Second City. Take in drinks and a show, and you might just catch the next Mike Myers, John Candy or Eugene Levy. (Warning: Those who sit up front could well become the subject of the performer’s next punchline.)
12. Open Roof Festival
What do you get when you pair live local music with an open-air film screening? The perfect date night, of course! Every Wednesday throughout the summer, the Open Roof Festival at 99 Sudbury Street offers the indie answer to “dinner and a movie,” complete with beer and snacks, including popcorn. (Note: It’s held in a parking lot rather than on a roof-but don’t let that hold you back.)
13. Pedestrian Sundays at Kensington Market
This boho village, filled with funky thrift shops, eclectic eateries and fine food markets, closes to traffic on the last Sunday of every month from May to October. Join in the pedestrian takeover, strolling the streets to the sounds of live bands and street performers. Bring your appetite so you can stop for Seven Lives’ celebrated tacos and a slice of award-winning cherry pie from Wanda’s Pie in the Sky.
14. Le Tour de Café
Torontonians take their coffee seriously and you, too, can become a coffee connoisseur thanks to Le Tour de Café. It’s a guided tour through some of the top java stops in the city’s east end, including tastings, teachings and roasting demos.
15. Toronto Pride
Toronto Pride is more than just a parade! Enjoy a full weekend of festivities, with food trucks, beer gardens, live music and drag shows. It’s a morning-to-night street party is where dressing eccentrically is celebrated and dancing on the street is encouraged.
16. Toronto Fringe Festival
Expect the unexpected at the city’s largest theatre festival, where 150-plus indie plays and comedy shows are held over 12 days in venues across the city. The Fringe Festival line-up is chosen by lottery and anyone can apply, so it’s an anything-goes outlet for students and emerging artists to make their mark. The best part? Tickets go for $12 or less a pop.
17. “Off-Mirvish” Theatre
Toronto boasts a stellar theatre scene, and though the big Mirvish musicals are a small splurge, tickets for lesser-known plays often go for a song. Check out the line-up at alternative theatre venues like Randolf, Lower Ossington, Buddies in Bad Times and Factory.
18. Toronto Marlies
Toronto Maple Leafs tickets may be notoriously hard to get your hands on, but the Toronto Marlies are much more accessible-and easier on the pocketbook. As the Leafs’ farm team, this AHL team is a gateway to the NHL, so you might be getting a sneak peek at the Leafs’ next MVP.
19. Steam Whistle Brewery
One of Toronto’s top microbreweries, the award-winning Steam Whistle is fittingly headquartered in what was once a steam train service station owned by the Canadian Pacific Railway. Take a behind-the-scenes tour of the National Historic Site, and then sample some suds. Sipping this premium pilsner at the foot of the CN Tower will have you raising your glass in a toast to Toronto.
20. Paddle boarding
A hybrid of surfing and canoeing, paddle boarding has been a popular watersport along the Toronto shoreline for several years. Take private or group introductory lessons (there are tons on offer and take 1- to 1-1/2 hours), strike your best balance and take to the water.
21. Summerlicious and Winterlicious
If you have a bucket list of restaurants to try, this is the time to tackle it. For two to three weeks, more than 100 restaurants across the city (past participants include Origin North, Canoe and Momofuku) offer three-course prix-fixe lunch and dinner menus, ranging from $18 (for lunch) to $48 (for dinner). Check this season’s participating restaurants, prices and full menus in advance on the Summerlicious website.
22. Haunted Walks
Love a good ghost story? Perhaps you’re brave enough to consider a late-night ghost tour of University of Toronto’s downtown campus. Marvel at the moonlit Gothic Revival architecture while revelling in its haunted history. Warning: You might need to leave the lights on after hearing about the little girl in the Planetarium.
23. Clay class at Gardiner Museum
Sculpt a masterpiece at the Gardiner-Toronto’s ceramics museum-where professional potters will advise budding artistes of any skill level. Drop-in classes are held every Wednesday, Friday and Sunday, or sign up for a weekly course to hone a specific skill.
24. Treasure hunting at the Sunday Antique Market
Antique furniture, vintage jewellery, obscure collectibles-oh my! Toronto’s St. Lawrence Sunday Antique Market is the prime place to dig for a diamond-in-the-rough. Go early, be ready to bargain and look for the lady who transforms old utensils into bracelets, rings and key chains with a provenance. Amazing!
25. Dig into Chinatown
Toronto’s vibrant, bustling Chinatown overwhelms the senses with its colourful shops, herb stores and authentic eats. Swatow’s shrimp dumpling soup is drool-worthy, but you also can’t go wrong dining at New Ho King, Lee Garden or Pho Hung. And good luck walking out of B & J Trading or Plaiter Place without snagging a bargain-priced souvenir.
26. Taste of Toronto
Meet Canada’s culinary geniuses, taste dishes from Toronto’s top restaurants and learn new cooking skills through live demos and hands-on classes at this elite foodie festival held at the end of June in Garrison Common at Fort York. Pictured above, last year’s celeb chef attendees (left to right) Ted Corrado, Darby Piquette, Mark McEwan, Michael Bonacini and Eric Chong.
27. A new kind of sports bar
Instead of simply watching the game at the bar, get active and start a match of your own. A fashionable new take on the sports bar is popping up across Toronto in which *you’re* the one breaking a sweat-drink in hand, of course. Play ping pong at Spin, go bowling at Ball Room, and try your hand at bocce ball and shuffleboard at Track and Field.
28. Summer Symphony in the Gardens
Step into Casa Loma’s grounds and you’re instantly transported into a fairy tale. Enjoy an enchanted evening under the stars every summer Tuesday, when the Toronto Concert Orchestra plays in the glass pavilion of this urban castle’s gardens.
29. Daybreaker Rave
Want to start your day with the same energy you’d normally save for Saturday night? Put on your wackiest workout clothes, lace up your dancing shoes and kick-off your workday with this carefree sunrise dance party set to live music and DJs. Go early for pre-dance yoga and enjoy healthy breakfast bites, coffee and juices.
30. Diner en Blanc
A movement that started in Paris more than 25 years ago, Diner en Blanc is an annual al fresco dinner, where thousands wear their best whites, pack a refined picnic and get taken to a surprise location to eat, drink and dance under the moonlight. This is one of Toronto’s hottest ticket, so you’ll have to register for the waiting list well in advance.
31. Sunning in Trinity Bellwoods Park
Spend a lazy summer afternoon sunning in Trinity Bellwoods Park-a popular hangout for the city’s young and hip set. Bring a blanket and Frisbee, and be sure to treat yourself to an ice cream sandwich from Bang Bang.
32. Axe throwing
Ever fancied yourself an urban lumberjack? Test your marksmanship (and brute strength) with axe throwing-a sport that’s rapidly risen in popularity in Toronto. Gather a group of six or more friends for a private lesson and tournament at the city’s Backyard Axe Throwing League.
33. Harbourfront Centre’s DJ Skate Nights
The best place to embrace a polar vortex is the Natrel Rink at Toronto’s Harbourfront Centre. Every Saturday night throughout the winter, skaters take to the ice for DJ Skate Nights, gliding along to the beat of lively tunes.
34. The Marilyn Denis Show
Be on TV-or at least in the studio audience-during a live taping of Canada’s most beloved daytime talk show. Go to The Marilyn Denis Show website to request your spot well in advance, as tickets are in high demand.
35. Shakespeare in the Park
On weeknights and weekend afternoons, Canadian Stage continues the summer tradition of Shakespeare in Toronto’s High Park. Plan your attendance based on your mood: generally, a comedy and tragedy perform on alternating days. At $20 or PWYC (that’s “pay what you can”), this theatre series makes summer days all the more lovely and temperate.
36. Evergreen Brick Works Farmer’s Market
When it’s cold, grab a spiked coffee and sit by the fire; when it’s warm, stroll the surrounding trails of the Don Valley. Whatever season you visit the Evergreen Brick Works Farmer’s Market (open all weekend in the summer and on Saturdays in the winter), you’ll have the opportunity to stock up on some of the city’s best local eats.
37. Come Up To My Room
This annual design event held at the Gladstone Hotel-Toronto’s oldest continually operating hotel-sees artists and designers transform rooms into absurdist interior design installations. Including a variety of interactive programs, the exhibition closes with an epic dance party, appropriately dubbed the Love Design Party.
38. Toronto’s music festivals
Music festivals are synonymous with summer, and Toronto has a ton of hot tickets on offer. Indie rock and pop lovers will discover new bands and enjoy current favourites at North by Northeast, Bestival and Field Trip; EDM fans will be in their element at Digital Dreams, Electric Island and Veld; and Drake’s own hip-hop/comedy OVO Fest brings surprise celebrity headliners every year.
39. Toronto’s outdoor art fairs
Find the perfect piece for your gallery wall at one of Toronto’s many outdoor art markets. From Riverdale Art Walk to the Liberty Village Art Crawl, these weekend fairs display rows upon rows of works by artists both established and emerging. One of the largest, Toronto Outdoor Art Exhibition, has been held in Nathan Phillips Square since 1961.
40. Jane’s Walk
A movement started by urban activist Jane Jacobs, Jane’s Walk is a festival of free neighbourhood walking tours led by the people who actually live there. It’s the best way to explore parts of the city you might otherwise never see.
41. Friday Night Live at the ROM
Dance among dinosaurs and feast alongside fossils at the Royal Ontario Museum’s Friday Night Live. This after-hours museum adventure, held every Friday through spring, pairs live music with ancient history.
42. Yoga at the AGO
Yoga at the Art Gallery of Ontario gives you the opportunity to get centred in the presence of great masterpieces. Hosted twice weekly in Frank Gehry’s iconic glass-and-wood Galleria Italia, it’s an inspiring way to start (or finish) your day.
43. Toronto Film Festivals
The Toronto International Film Fest (TIFF) might draw the red carpet royalty, but it’s not the only film festival in town. Hot Docs, Inside Out and Toronto After Dark are a few other favourites, but there’s something for everyone-even cat lovers. (And by that, we’re referring to the Just for Cats Video Festival. Yes, seriously.)
44. St. Lawrence Market
Hailed as one of the top food markets in the world, Toronto’s St. Lawrence Market serves up farm-fresh fare with a side of history. Not only does the building date back to 1904, but a market has existed on the site since 1803. Shop hundreds of vendors while sipping one of the best coffees in the city (Everyday Gourmet) and make a souvenir of some artisanal mustard from Kozlik’s Canadian Mustard.
45. Woofstock
The largest outdoor festival for dogs in North America, Woofstock plays host to 15,000 dogs (and dog owners) annually. With vendors selling every doggy indulgence, as well as doga (dog yoga), stunt shows, fashion shows and pageants, this event is a pooch-lover’s dream.
46. Toronto’s craft beer festivals
Whet your whistle taste-testing local brews at some of Toronto’s top craft beer festivals. Sample the Roundhouse Winter Craft Beer Festival, Summer Craft Beer Fest at Liberty Market and the Hart House Craft Beer Festival (pictured) for laid-back vibes and lots of fun.
47. One of a Kind Show
A celebration of all things Canadian and handmade, the twice-annual One of a Kind Show is the best destination to find unique gifts. Between the gourmet goods, clothing, jewellery, ceramics and art, you’re guaranteed to find the perfect present for even the most impossible person to buy for.
48. International Festival of Authors
A forum for literati and book lovers alike, the International Festival of Authors (IFOA) brings Canadian and international writers, poets and playwrights together every October. Head down to event HQ at Harbourfront Centre for 11 days of readings, book signings, interviews and lectures.
49. T&T Supermarket Waterfront Night Market
“Midnight snack” takes on a new meaning when you’re trying squid on a stick, stinky tofu and grilled pig’s feet. You’ll find these (as well as less-daring fare) at this vibrant late-July pop-up market on the Toronto waterfront.
50. Free Concert Series in the Richard Bradshaw Amphitheatre
Free concerts from the internationally acclaimed Canadian Opera Company? Yes please. Held Wednesdays and Thursdays at noon in the light-filled Four Seasons Centre, the concert series showcases musicians from a range of genres, including piano, jazz, chamber and world music.
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50 Reasons to Visit London
10 Must-See Attractions in Montreal and Quebec City
