The Toronto skyline at sunset

Weekend in Toronto


What to see and do in one of the world’s most vibrant and diverse cities

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I feel uniquely positioned to tell you why you should spend a weekend in Toronto. I lived most of my life here, before moving to Denver in 2010.  I’ve returned every year for the last ten, and make a point to enjoy it as a visitor would. Things that locals might not notice or appreciate are fun for me. Cue my excitement at the streetcar rumbling by.

I began keeping a “Toronto list” for my American friends who asked for advice on touring my home city. It got a bit unwieldy so I’ve streamlined that list into this guide — my recommended things to see and do in one of my favorite cities, whether for a weekend or a week.

Rather than give you a specific itinerary, I list my top recommendations; you can customize your itinerary based on what’s most of interest and explore the city at a pace that feels right for you. Toronto, like most of the world’s great cities, is best explored by visiting attractions and also taking time to just wander around the city streets. It has a wonderful transit system (subways, streetcars and buses), but I recommend you also walk from place to place if weather permits. You’ll see more that way

Toronto's CN Tower with red leaves in the foreground. Fall is an ideal time for a weekend in Toronto

When to Visit Toronto

As far as when to visit Toronto, I have an “informed opinion”. I spent much of my life here, which adds up to a lot of blustery grey winters and hot muggy summers. The best time to visit Toronto is in the fall, the second-best is spring. Summer comes next, unless you want to spend time on an Ontario lake after your city visit (which I highly recommend – in that case visit in summer). I don’t suggest you visit Toronto in winter – winters are typically cold, damp, windy and grey, not ideal when this city is best explored on foot. (There’s a reason that Torontonians make their way around downtown via underground tunnels in winter.) 

Map of Toronto

Explore, Eat, See & Stay

I created this map with many of the suggestions in this guide included, to give you a sense of the city and help you plan your weekend in Toronto.

Weekend in Toronto Guide

Front Street Toronto with a mix of historic and new building and a Canadian flag

Popular Toronto Attractions Worth Seeing

A Rodin sculpture in a soaring gallery at the Art Gallery of Ontario in Toronto
The exterior of the Art Gallery of Toronto

Art Gallery of Ontario

A collection of over 90,0000 works of art including paintings from Canada’s Group of Seven who are famous for their beautiful landscapes. The gallery hosts many visiting exhibitions; I saw a fascinating Andy Warhol exhibit on my most recent trip. The architecture is fabulous with a glass-and-wood façade on one side that makes viewing the city a part of the experience. I love this museum. It’s one of my favourite things to do in Toronto. Don’t miss the Galleria Italia – the sculpture gallery with gorgeous architecture and city views. 

The exterior of Toronto's Royal Ontario Museum with it's combination of new and old architecture

Royal Ontario Museum

Founded in 1914, the Royal Ontario Museum features a huge collection of nature, culture and art from around the world. It is Canada’s largest museum with 13 million items.

If you don’t have time to visit, walk by the ROM and check out the exterior. A 2007 addition known as The Crystal was added to the historic building from 1914.  It looks like it sounds –  as if a giant crystal crash landed on an unsuspecting stalwart of a museum.  And it’s the subject of great debate – Torontonians seem to either love it or hate it. I like it; if you go, let me know what you think. 

The interior is really striking as well stunning and it’s conveniently located right on the subway line near Yorkville, a neighbourhood worth exploring if you enjoy shopping (more below).

Susan Heinrich in her home city of Toronto with the CN Tower in the background
The Toronto skyline at night with the CN Tower and Rogers Centre lit up

CN Tower

You don’t need to ride to the top to appreciate Toronto’s most famous attraction, the CN Tower, or “tall tower” as my kids called every time we drove past when they were little.  

I remember when it was built in 1976 – then the tallest free-standing structure in the world, it was astounding. And it still is. In 1995 it was classified as one of the Seven Wonders of the Modern World by the American Society of Civil Engineers. It’s a telecommunications hub with a range of attractions and dining, including a rotating restaurant with amazing views and expensive food. If you’re brave you can do the “EdgeWalk” experience. This sounds so terrifying to me I can’t even describe it you. 

Again, you don’t need to go up the tower to enjoy it – admission is pricey. You’ll see it many times, day and night as you explore the city. Don’t forget to get a selfie and tag me if you post it on instagram: midlife.globetrotter.

A shark swims above coral in a tank at Ripley's Aquarium in Toronto Canada

With Kids & Teens - Ripley's Aquarium

 A recent addition to Toronto and a good one. I enjoy aquariums and Ripley’s is really well done. It’s the perfect rainy day activity and ideal with kids and teens. Don’t miss petting the slippery rays at Stingray Bay. And if you are dreaming of a tropical getaway head to Rainbow Reef, the 200,000-liter home to over 100 species of fish. 

The colourful Toronto sign in Nathan Philip Square Toronto

Toronto Entertainment

King Street Theatre District

Toronto has a robust theatre scene, a combination of Canadian productions and big Broadway shows which come through. If you enjoy live theatre there is lots to choose from (note that popular shows can sell out weeks or months ahead).  “Come From Away” is a delightful Canadian production, funny and poignant, so I recommend you see it if you have the chance. I don’t suggest you have dinner right near the theatres, however. You’ll find better restaurants further west on “King West”, the stretch west of Spadina Avenue. 

Second City Comedy Club

One of two locations of this historic comedy club, the other is Chicago. Many of he most famous American and Canadian comedic actors got their start at Second City, including Dan Aykroyd, Gilda Radner, John Candy, and Eugene Levy. Explore a listing of current shows: Second City Toronto Shows.

Four Seasons Centre for the Performing Arts

A gorgeous glass-enclosed building built specifically for opera and ballet. If you are a fan of either, make a point to get tickets and enjoy the exceptional acoustics. The Canadian Opera Company presents six operas each season and the National Ballet of Canada has a similar number. Check for other events for the dates of your visit. The venue sometimes puts on special concerts. 

Massey Hall

Many of us from Toronto remember a great live music experience at Massey Hall,  Canada’s oldest concert hall, which opened its red doors in 1894. Find current listings here: Massey Hall Upcoming Shows.

Exploring Toronto's Vibrant Neighbourhoods

Queen Street West in Toronto

Queen Street West

Vogue magazine called Queen Street West the coolest street in the world. Queen Street really encompasses the multi-cultural and hip flair of Toronto. You can experience cuisine from many different cultures and creativity abounds here, both in the street art and boutiques. Ideally, you should walk along Queen from Spadina all the way to Ossington Street – the west end of Queen has more upscale boutiques. There are endless food to try: but I will suggest Vietnamese Bahn-Mi sandwiches at Banh Mi boys and delish Asian-inspired ice cream at Kekou Gelato (I loved the Hong Kong Milk Tea flavour). 

As you get closer to Ossington, the shops get a little more upscale. Be sure to check out Suzy Rohar for her incredible scarves, Eighteen Waits for beautiful men’s clothes and other collectibles made in Canada. And for trendy shopping check out Gravity Pope if you like prints by Marimekko and a unique selection of very nice shoes and other items.

When you are ready for a drink, stop by the Drake Hotel and in nice weather head up to the Sky Yard to enjoy the art murals and well-crafted cocktails. There is also a nice book store on Queen called Type Books. 

I am really only scratching the surface here. Queen Street West needs its own guide. I think this is also a great area just to explore without a  guide and enjoy the discoveries you make. 

A shop on Queen Street West called 18 Waits with a handmade Canadian flag
The 18 Waits men's shop on Queen Street West
The Gravity Pope store on Queen Street West is a nice space with a staircase and chandelier
The Gravity Pope store on Queen Street West


Yorkville is a chic area with upscale shops and dining. The Royal Ontario Museum is nearby, if that’s of interest as well as the Gardiner Museum. Bloor Street, the main west-east thoroughfare of the city has the big-name luxury brands such as Hermes while the smaller streets north of it which make up the Yorkville have smaller boutiques as well as nice restaurants.

For a lunch break during your shopping. I really like the Oxley Gastropub, a charming space with a cool Britannia vibe and delicious food (full disclosure, my friend’s husband is the owner.) Trattoria Nervosa has yummy Italian in a pretty space and the dbar lounge in the Four Seasons hotel is a nice place for a cocktail. For a quick bite and great coffee, sandwiches and pastries head to Café Mercurio. 

The Yorkville neighbourhood of Toronto
The Yorkville neighbourhood of Toronto

Kensington Market

More a neighbourhood than a market, this area is a vibrant series of narrow streets and Victorian row houses. It’s also designated a national historic site of Canada because it has been home to numerous waves of immigrants since the beginning of the 20th century. Its early residents were British and Irish immigrants. My dad told me his mother used to send him here to buy butter when he was a boy in the 1940’s and lived on nearby Spadina Avenue. At that time it was known as Toronto’s Jewish quarter. Later years saw an influx of immigration from Eastern Europe, Portugal and Italy followed by Afro-Caribbean, Chinese and East Indian.  All of these cultures are represented here. I highly recommend a visit!

Toronto's harboufront on Lake Ontario with the Toronto islands and a ferry in the distance

Harbourfront, Toronto Islands & Lakeshore Path

Toronto’s harbourfront has been undergoing a slow revival. Poor urban planning had created a separation between it and the rest of the city – but that is changing. While I would not say visiting the harbourfront is a top priority, I recommend taking the ferry from the Ferry Terminal to Toronto Island, a 15 minute ride that costs about $9 return and runs very 30 minutes. You will get spectacular city views and enjoy a little time on the island where you can visit one of the cafes or walk around and admire the adorable houses on Ward’s and Algonquin Islands. There are about 260 homes with 650 people living here. There’s also an amusement park called Centreville if you are traveling with young kids.

A pedestrian and bike path also runs along the edge of the city next to Lake Ontario. It’s another great way to see the lake on one side and the city on the other.

If you are interested in getting out on Lake Ontario and taking a tour of Toronto’s waterfront. This tour is very popular: Toronto Harbour & Islands Cruise.

Historic buildings in Toronto's Distillery district date to the 1830's

The Distillery District

The historic Distillery District dates to the 1830’s, when Toronto was still the town of York in the British colony of Upper Canada. This was the site of the Gooderham and Worts whiskey distillery, one of the largest distillers in Canada at the time. The historic buildings remain and now house art galleries, restaurants & charming shops with Canadian goods. Special events are regularly held here and the annual Christmas market is very popular if you are here in December. 

St. Lawrence market on a weekend in Toronto
St. Lawrence market on a weekend in Toronto

Front Street

There are a few attractions worth seeing here: the St. Lawrence Market, the Gooderham building, a beautiful “flatiron” completed in 1892, and Toronto’s Union Train Station which is being redesigned. And for the hockey fans the Hockey Hall of Fame is nearby as well. 

The historic St. Lawrence Market is worth is a stop for breakfast or lunch. Try a traditional Canadian peameal bacon sandwich at the Carousel Bakery. There is an exceptional assortment of cheese at Alex Farm and you can sample Montreal-style bagels at St. Urbain. There’s been a market here since 1803 when the town of York had grown sufficiently large, and the current building dates to 1902.

Susan Heinrich stands looking at Toronto's flatiron building, the Gooderham building completed in 1892
Susan Heinrich on Front Street with the Gooderham building beyond

Dundas Square & The Eaton Center

Dundas Square is a sort of mini version of New York’s Times Square with glowing billboards, street performers and shops. It’s across the street from the Eaton Center Toronto’s largest shopping mall with soaring ceilings. This area would be low on my Toronto list unless you really love to shop at established big-name brands, or are with teens or young adults who love to shop. Even then, try and convince them to go to Queen Street West instead. 

Toronto Food - What to Eat

Toronto is one of the world’s great food cities so to do it justice I am working on a separate guide – coming soon. In the meantime, here are a few things you should try, some of which I’ve already mentioned:

Poutine. Apparently, french fries with cheese curd and gravy are so objectively delicious they are now also found outside of Canada. But if you want to try “Canadian poutine” go to Smoke’s Poutinerie (multiple locations).

Montreal bagels. It’s the classic rivalry, Montreal or New York bagels and although I now live in the U.S. and love New York, Montreal bagels will always have my heart. They are denser, chewier, and just, better.

Susan holds a portuguese tart from Venezia bakery in Toronto
A portuguese tart from Venezia bakery in Toronto
A plate of oysters on ice with a lemon and red sauce
Price Edward Island (PEI) oysters at Farmhouse Tavern in Toronto

Butter Tarts. As sweet treats go, these are really sweet, almost too sweet. But these small pastries with a filling made of butter, sugar and eggs are truly Canadian. I like the ones with nuts and dislike the ones with raisins, but you should taste both and decide for yourself. Or go with the classic, straight up gooey filling. The delicious Portuguese custard tarts are also found around the city, thanks to a large Portuguese community here. Try one if you see it, especially if you are in Little Portugal. 

Prince Edward Island Oysters. Canada’s smallest province is nice enough to share their scrumptious oysters with the rest of us. They are smaller than some from other places, and I think especially yummy. So if you happen to see them on a menu, give them a try. 

Indian dosas. Toronto has a large South Asian population and incredible Indian food to go with it. I particularly love dosas. And samosas. And curries. And chana masala. You get the idea – Indian food is almost always a good idea in Toronto. Indian rotis are also widely available and yummy.


Loaded Pierogi restaurant in Toronto

Pierogis. These Polish dumplings were mostly found in the west end of the city where much of Toronto’s polish immigrants settled. But they can also be found at the St. Lawrence Market as well as a chain called The Loaded Pierogi which has taken creative pierogi flavours to new highs, or lows. Double cheeseburger pierogis are a fusion gone too far – stick with the classic – cheese and potato – at least to start.   

Naples-style thin-crust pizza. It’s as good in Toronto as almost anywhere I’ve had it (although I’ve yet to visit Naples). Terroni is considered to have among the best Naples-style pizza in Toronto. I really like their Adelaide Street location in the former courthouse building where you will pass the holding cells which remain downstairs, on your way to the bathroom. Pizzeria Libretto is also great (two downtown locations). As far as delish slices, “King Slice” is king – it’s on Queen Street West.  Pizza Libretto is also great and now has multiple locations. Reserve ahead if you have time. 

Toronto's Kimpton St. George Hotel is a great location in the heart of the city

Weekend in Toronto - Where to Stay

There are many good hotel options and because I lived here I haven’t actually stayed in as many hotels as somewhere like New York. But I am including a few suggestions.

Midtown Toronto Hotels

On my most recent visit in July of 2021, I stayed at the Kimpton St George Toronto because I have enjoyed Kimpton hotels elsewhere and I really like the central location. It was even nicer than I expected. It’s a former Holiday Inn, but you would never know. The decor is gorgeous and the rooms are well-designed. It is also well-priced compared to the other hotels in this neighbourhood which are typically very pricey to go along with the Yorkville location. You are right on the subway line here, and can get downtown quickly. In addition to the Kimpton, this area has a Four Seasons – lovely and pricey as elsewhere. But if you want luxe in midtown Toronto I recommend The Hazelton. I haven’t stayed here but would love to; it’s the #1 ranked hotel for Toronto on TripAdvisor and looks lovely.  

Downtown Toronto highrises at night

Downtown Toronto Hotels

If you would rather stay downtown, closer to the bulk of the attractions, I have stayed at Le Germaine Toronto Mercer and enjoyed it. It’s stylish with a great location. If you want a luxury hotel there are several choices. The hot new place to stay in Toronto is called The Bisha, a stunning space with a rooftop infinity pool. The big-name luxury hotels are all here as well, within in a few blocks of each other are the Ritz-Carlton the St. Regis and the Shangri-La

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A red streetcar travels past highrise buildings on downtown Toronto

You may be realizing that a weekend in Toronto might not be enough. You’ll just have to return!  You can’t expect to see North America’s third-largest city in a single trip (Excluding Mexico, Toronto’s population puts it third after New York City and Los Angeles.)

Sometimes people say it’s like a smaller New York, but it’s actually more similar to Chicago, very close in size and both set on one of the “Great Lakes”. But Toronto’s diversity makes it unique: there are over 250 ethnicities represented in the people of Toronto with 180 different dialects spoken. And over half of the city’s population is foreign born! So get ready to “guess that language” while riding the subway or streetcar –  another of my favourite things to do while in Toronto. 

If you enjoyed this Weekend in Toronto guide you might also enjoy a guide to a: Weekend Away in Venice Beach, California

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About - Midlife Globetrotter

Hey there,

I’m glad you’re here. Can we talk about midlife? I reached my late 40’s, realized my kids were growing up, and adventure began calling in a new way: big travel adventures as well as everyday ones. I want Midlife Globetrotter to be a place where we explore how to add a sense of fun, freedom and meaning to these precious years. Let’s celebrate how far we’ve come, and all that’s ahead.




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