Things to Do in Toronto in Your Twenties

Toronto at twilight
Toronto at twilight | © Rick Harris / Flickr

There’s plenty to do in Toronto if you’re young, adventurous, and looking to have some fun. Whether you’re interested in staying up all night or spending a lazy afternoon with your friends, here are some of the best activities you can do around the city in your twenties.

1. Dance and skate an evening away

Skate Park

Every winter, the Harbourfront hosts DJ Skate Nights on the Natrel Rink. This free skating dance party runs every Saturday from December to February, and it’s a great way to have a fun night out even when the temperatures dip well below zero.

2. Experience the magic of the Christmas Market

Market

The Christmas Market in the distillery District in Toronto.
© Jonny White / Alamy Stock Photo
Toronto’s Christmas Market has been called one of the top 10 Christmas markets in the world by Fodor’s Travel, USA Today, and others. Every year, the market can be found in the historic Distillery District, a romantic area that makes this holiday tradition feel particularly special. Along with the numerous vendors, you can enjoy traditional music and carols, dance performances, and other events.

3. Raise a toast at Toronto Winter Brewfest

Building

If you’re looking to refine your beer palate, head over to the Enercare Centre’s Heritage Court at the Exhibition Place to explore more than 150 craft beers from across Ontario and Quebec at the Winter Brewfest. You can balance it out by sampling the delicious gourmet food from Toronto’s best food trucks, also at the festival.

4. Participate in IceFest

Park

For the past 12 years, Toronto’s elegant Yorkville neighbourhood has hosted IceFest, which showcases incredible ice sculptures along with live ice carving demonstrations. Last year, 20,000 lbs. of ice were used. For a unique winter experience, you can explore the place where Canadian winter meets artistic expression. There’s always a fun Photo Opportunity Area featuring spectacular ice creations that you can tag across social media.

5. Belt it out at a Leafs game

Stadium

Hockey is Canada’s game, and what better way to experience the country’s energy and passion than by heading over to the Air Canada Centre and watching some? Torontonians remain loyal to their home team despite the Leafs’ relatively disappointing record. Going to a hockey game is a must-have experience while in your twenties.

6. Go to Winterlicious

Restaurant, Japanese

Winterlicious is one of Toronto’s best foodie events, where you can explore the city’s lively culinary scene through delicious three-course prix fixe lunch and dinner menus served up at more than 200 restaurants. There are also other culinary events like cooking classes and demonstrations, so you can start making yourself more than just macaroni and cheese dinners.

7. Spend a night out on the town

Art Gallery, Building, Cinema, Concert Hall, Movie Theater, Music Venue, Opera House, Theater, Theatre

The city has a vibrant clubbing scene, mostly concentrated in the Entertainment District, and your twenties are the decade for having fun deep into the night and the wee hours of the morning. Toronto’s trendiest nightclubs are always a good bet for an unforgettable night out.

8. Experience dizzying heights

Architectural Landmark

Toronto, Canada: CN Tower detail or details during the day
© Torontonian / Alamy Stock Photo
Edgewalk at the CN Tower is perhaps the best opportunity that Toronto has to offer for putting your youthful bravery to the test. This is the highest hands-free walk in the world, and it’s sure to be an unforgettable experience. Another fun event you should do while you’re still young and strong is test your thigh muscles with the annual CN Tower Stair Climb in April, a WWF-sponsored charitable event that raises money for a worthy cause: the environment.

9. Go to a Raptors game

Sports Center, Stadium

Even if pro sports aren’t your thing, going to a Raptors game is always fun. Basketball has been heating up in Toronto in the past few years, with support from local celebrity Drake and the infamous “We The North” campaign.

10. Eat, drink, and be merry on a patio

Bar, Pub Grub

Flight Deck at the Pilot in Yorkville
Courtesy of the Pilot

Whether you’re going for brunch, drinks, coffee, or dinner, a patio is always the best choice during the warmer months. Toronto is home to countless outdoor spaces for eating, drinking, and relaxing with friends, which range from crowded to cozy, chic to more rustic. Check out The Pilot in Yorkville for after-work cocktails, or Java House on Queen West for cheap eats and drinks during the summer.

11. Indulge in Summerlicious

Restaurant, Chinese

R&D Interior 1 -
© Cindy La

If you missed Winterlicious, then Summerlicious is your opportunity to enjoy some of the city’s best eats while relaxing on a patio. For three weeks in the heat of July, you can enjoy three-course prix fixe menus across the city.

12. Party it up at a museum

Building, Museum, Park

The Royal Ontario Museum and the Michael Lee Chin Crystal Modern addition.
© John Zada / Alamy Stock Photo
During May and June, Toronto’s favourite Friday night hang out spot is, unexpectedly, the museum. Every Friday, the Royal Ontario Museum (ROM) hosts its wildly popular Friday Night Live events, a themed party that features live indie artists, top DJs, and an array of food and drinks. You can dance the night away or explore the ROM’s stellar galleries. Grab a bunch of your friends and get 20% off a group of 20 or more.

13. Spend a day at the Toronto Islands

Park

Visitors leaving the ferry at Torontos Centre Island park
© Steven Chadwick / Alamy Stock Photo
Take the short, cheap ferry ride from the city’s downtown core over to the peaceful Toronto Islands. Their green spaces, bike paths, beaches, and boardwalks that will almost make you feel as though you’re enjoying a cottage getaway. It’s a great way to get away from the rush of the city and enjoy a summer afternoon with friends.

14. Have a beach day

Natural Feature

Even if you don’t want to submerge yourself in the cold water just off Toronto’s urban waterfront, the city still offers plenty of beach space to enjoy an afternoon in the sand and sun. There are beaches on the Islands, of course, but you can also head over to the popular Ashbridges Bay Park in the city’s east end. Bring a towel, shades, and sunscreen.

15. Cycle the length of the Lakeshore

Hiking Trail

Toronto’s Waterfront Trail spans the northern shore of Lake Ontario from Scarborough in the east to Etobicoke in the west. During the warmer months, the trail is a popular space for joggers, families, ice cream trucks, swimmers, picnickers, and cyclists. Since it’s mostly a flat route, biking the length of the lakeshore is an enjoyable and relatively easy activity. You can choose to take it slowly and enjoy a long summer afternoon meandering along the shore, or aim to set a personal record.

16. Experience the city by kayak

Building

Whether you’re at the Islands, the Harbourfront, or further west at the mouth of the Humber River, you can rent a kayak or canoe and explore the city’s waterways. Add a little nature to your urban life by taking lessons or following a guided tour of the local wildlife and ecosystems.

17. Go to a Jays game

Stadium

Toronto Blue Jays Major League Baseball stadium Rogers Centre
© Robert Quinlan / Alamy Stock Photo
On weekend afternoons in the summer, you’ll find a lot of young people heading over to the Rogers Centre to watch the city’s baseball team play. Have a beer or a foot-long hot dog, ice cream or fries, and enjoy a leisurely ballgame. Maybe the Jays will even win this time.

18. Attend a music festival

Park

Summer music festivals are a definitive experience, and there’s no shortage of fun, annual music events to attend across Toronto’s green spaces and concert venues. Among many others that span from rock to heavy metal, classical to a cappella, there’s TURF and the electronic music festival called Veld, the Toronto Jazz Festival, and the annual music event hosted by Drake: OVO oFest.

19. Spend all night exploring contemporary art

Building

In September, Toronto’s favourite contemporary art night, Nuit Blanche, takes over the city. The range of installations, exhibits, and events will easily keep you up all night—perfect for young, exploratory creatives. Other must-see art events in Toronto include the more performative Luminato, and Fashion Art Toronto.

20. Go to the Ex

Building

Throughout childhood, the arrival of the Exhibition signaled the end of summer vacation, heading toward Labour Day and the start of a new school year. Around since 1879, the Ex attracts around 1.5 million visitors annually and is Canada’s largest annual fair. There’s always something nostalgic about it, and it’s not just for kids! Spend a late-summer afternoon trying a few of the rides (if you dare), tasting the strange food concoctions that have become part of the CNE’s tradition, or wander through the stalls at the International Pavilion.

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