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Canada Summer Road Trip! Montreal and Greater Toronto Edition

In this post I’ll outline the ultimate itinerary of what to do in Canada during the summer. Together we’ll explore summer activities in the Greater Toronto Area, Montreal, and a collection of Canada festivals along the way.

Places to visit in canada during the summer
Canada’s side of Niagara Falls

Canadian Summer Road Trip Guide

Oh, Canada.

I miss your green spaces, clean air, diverse culinary palette, and mostly on-time public transport.

After almost 10 years abroad, it’s time to visit my home country in a very serious way. And what better way to do it than to visit the places I know best –those that never disappoint, won’t break the bank, and where there’s plenty of ways to enjoy a Canadian summer with old friends and cheap Airbnb accommodations.

Before you head to Canada, sign up for Airbnb with this link and get some free credit for your first night.

I’ll be bouncing back and forth for birthdays and Canada festivals taking place in Montreal, Toronto, Burlington, and Hamilton, with a stop in Niagara Falls.

Links open in a new tab so you don’t lose your spot on this page.

Canada Festivals
Taarrraaahnahhhhh (aka Toronto)

This trip will be a nice change of pace from Asia, as a lot has changed in good ol’ Canadia since I last visited.

Montreal’s world-class restaurants await, Toronto’s skyline has changed remarkably so there’s more to explore, and I get to take a long, bong-filled breather from the Philippines’ drug war. While I will loyally respect the laws of the countries I visit, I’m eager to enjoy my new rights in Canada.

Cannabis is legal, folks!

So buckle up. This is your Canada summer road trip guide to Montreal and the Greater Toronto Area, written by a nostalgic Canadian local.

Canada Summer

Happy to Be Your Canadian Tour Guide

If you’re wondering about my experience in Canada, I was born in Burlington, a city located within the province of Ontario. A suburb outside Toronto where Jim Carry lived in a car and attended my high school, around the time he wrote himself his first blank cheque. Beside that other suburb where Ryan Gosling was born.

Sandwiched between a couple years out West and a couple years out East, my adult life was spent in equal parts between Hamilton, Toronto, and Montreal before I became a proper digital nomad.

Canada Summer Hamillton Music Festivals
Hamilton, the City of Waterfalls among other great things

Quick Facts

Before we get started, let’s take a quick, high-level look at summer in Canada.

We’re freezing cold most of the year, so we really milk great weather for everything it’s worth. And that’s why Canada summers are worth the trip –so many festivals and attractions, so few warm months, they have to cram it all into a single season.

Canada Summer Months

Canada summer months in the Greater Toronto Area and Montreal are between May and September. The average temperature during these months floats around 16 – 26 Ā°C, or 61 – 78.8 Ā°F.

The official start to summer and the longest day of daylight for the year (Summer Solstice) is usually June 21 and it gets dark around 9pm. Yep, over 15 hours of daylight in a single day.

You can learn more about the weather, sunrises and sunsets here.

Great Canadian Road Trip
A section of Montreal waterfront

Getting to Canada

I’m a local, maybe you’re not. My wife isn’t (yet). And for non-locals I recommend travel to Canada with your ETA ready.

In my experience, getting into Canada is a cottage industry –unless you’ve got some sort of outstanding criminal silliness, an e-visa should be easy enough to obtain and most people won’t have any problems.

What to Pack

Summer in Canada is about as hot or sometimes hotter than temperatures in Thailand during the day, depending on where you are.

If you’d like to know what to pack for Canada, this packing list for Southeast Asia is as good as any.

Bring a pair of pants, socks, shoes, and a hoodie or light jacket because it still gets chilly at night (and some nice restaurants demand gents wear dapper-looking pants and footwear).

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Getting Around

Getting around between Montreal, Toronto, Burlington, Hamilton, and Niagara Falls is made easy with the following modes of public transportation:

  • Go Trains and Buses
  • Via Rail
  • Megabus
  • City buses, LRT, street cars, and subways
  • Uber

And then of course, there’s cheap flights from either Pearson or Billy Bishop airports in Toronto to Montreal’s Trudeau international airport.

Places to visit in canada during the summer

Toronto is massive. It’s too big. So I’ll be focusing on its downtown and waterfront. I recommend using the TTC in Toronto, it’s an integrated network of buses, light rail (LRT), subways and street cars, and you’ll need to pick up a “Presto” pass to use it. For everything else, there’s Uber.

We’ll also clip over to Burlington and Hamilton for some epic Canadian music festivals. City buses (that also use a Presto pass), LRT, or Uber are the way to go here. To get to Niagara Falls, I recommend a Go Bus, and once you’re there use Uber.

And then, finally –the City of Saints, Sin City, the City of Festivals; La MĆ©tropole du QuĆ©bec. Montreal. Their Metro subway system is pretty great, the bus system not so much because they won’t speak English in most cases –even if they can.

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Let’s Go!

For the sake of simplicity, I’ll break down each place to visit in Canada during the summer by city like an ‘a la carte’ menu, from North to South. I’ll kick them off with a little personal background, and then jump into summer activities for each.

What to do in montreal tonight
Jacques Cartier Bridge, Montreal


Montreal will be the big winner for tourists on this Canada summer road trip itinerary:

  • Easy to get around, more to do in a small area, space is limited like Singapore so they make the most of it –you can view a map of their Metro system here
  • Insane number of festivals going on, all summer long –because of this, the city feels a little like Ferris Bueller’s Day Off 24/7
  • Cheaper to Airbnb than both Toronto and Hamilton, lower cost of living as a result of a weaker job market –great for tourists, not so much for locals
  • Culture and architecture is a mix of both progressive and historic, most of the time you feel like in you’re in a good part of Europe
  • Culinary mecca; Montreal has a so many foods and restaurants it is well-known for –legendary poutine, bagels, smoked meats, and even much of the low-cost gastronomy is considered high-end in much of the world
  • Best night life in Canada in my experience, it’s easy to make fast friends and wind up at a house party around 3 -4 am, and last call is later here than in other provinces
  • Montreal events some how find a way to be something for everyone; you can bring little kids to these events, or you can be a debaucherous party animal –people tend to keep to their own business and won’t cause trouble if you’re not wearing a political statement on your t-shirt

For the single folk among my readers, the entire planet recognizes that Montreal is known for its beautiful people. And the French for their culture of sexual openness and liberation. If you can carry on an intelligent conversation, you’ll get along famously with the locals.

Language Police

Quebec has strong language laws to preserve their culture. In fact, a greeting by a business in English before French can award them a fine from the government big enough to shutter them. Bus drivers are not legally required to speak English, and most will not. Signage doesn’t even need to be in English, at all.

This would be a pain in the ass if the city wasn’t so accessible, and if Google didn’t do a great job of putting all their transit maps online in English.

Money talks, so most establishments popular among tourists will speak English fluently and you may not run into any difficulty communicating.

For Canadian tourists who don’t speak whatever they’ve done to French; just say you’re American and avoid the language politics altogether. Socially, Americans will get a pass and fellow Canadians will not in many cases.

Most people are “tolerant” of your inability to speak French as a Canadian, but it likely won’t win you any friends. Saying you’re from Toronto or Calgary and don’t speak a word of Canada’s other national language may not go over well, and you’re there to have fun.

I learned enough of the language to work and carry on a conversation and I still got slammed for my accent. The stuff we learned at school in the rest of Canada (ROC) is different than that of France, a flavour of French they don’t actually speak in Quebec. It’s comparable to Visayan vs Tagalog in the Philippines or Friesian vs Dutch in the Netherlands. Same same, but different.

What to do in montreal tonight

Montreal Viex Port (Old Port)

Montreal’s Old Port is a great place to start your trip in Montreal. The buildings around this area predate the incorporation of Canada as a country; founded by Paul Chomedey de Maisonneuve in the 16th century, the Old Port is the site where early French settlers first landed long before the British set foot here to conquer it.

Montreal was also an important battleground when Canadians took on the Americans in the War of 1812 (Canada won). Although it isn’t the oldest city in Canada, it’s historical European roots are very obvious.

Today, the Old Port of Montreal is a village apart from the rest of the city where you can take a horse-drawn carriage, explore the old alleyways, visit cathedrals, and enjoy a quality meal at a patio near the waterfront or on a rooftop with a view.

The Old Port draws people of every stripe, from Fortune 500 business conferences to celebrities and government officials from around the planet.

When I was a busboy at Hotel Nelligan around the time The Aviator came out I once served the likes of Leo DiCaprio, Hugh Jackman, and Lucy Liu room service and printed emails for Hugh –I knew Hugh Jackman’s email!

Things to do:
  • Rooftop meal at Hotel Nelligan; the food is top notch and the crowd is upper class, so dress for it
  • Montreal Science Centre, right on the water –and it’s surrounded by shopping containers (where I once met John Malkovich while selling F1 swag)
  • Horse carriage, cathedrals, a little park area with a fountain during the golden hour –all a top notch way to spend a day (had my heart broken at that fountain once)
  • Other events such as Eureka Festival and Through the Echoes listed on the Old Port of Montreal website
  • The grassy part near the water / Science Centre is a great place to sit down and meet people, brown bag your favourite bottle, smoke a doob, and then take in fireworks (which they do on a frequent schedule, check Old Port website above)
  • I found a bunch of Airbnb in the Old Port for about $20 USD per night –zing!

Montreal Summer

Piknik Electronique

I’ve got three Montreal traditions where I spend most of my time while there, and this is one of ’em.

Imagine an island just outside the island of Montreal across from the Old Port, accessible by Jean-Drapeau Metro subway station –a baby island, and on that island is a weekly rave that starts around lunch time every Sunday and goes into the evening.

Canada festivals

The whole island is full of families and party revelers alike, it’s surreal. For some, it’s good, clean, family fun and a time for a Sunday picnic. And yet, 20 feet away could be a guy dancing alone, peacefully tripping balls in the golden hour sun on ketamine and blow.

It’s an eclectic event of hipsters and families, all there for the music, the scene, a quality green space, an outdoor party, legal cannabis, and the allowance of BYOB if you pack food along with it. They check bags –if you don’t bring food, they make you dump the alcohol.

This is a decades old tradition with internationally acclaimed electronic music gods and goddesses, the likes of Misstress Barbara, et al.

No one throws a high calibre party in Canada on such as consistent basis as they do in Montreal. You can check Piknik Electronique on their website and Facebook page.

Tam Tams at Mt. Royal

Another Sunday tradition takes place at Jeanne-Mance Park, where the city converges at the base of Mt. Royal to chill on the grass, enjoy a brown-bagged beverage, smoke a blunt, and listen to the hundreds of leather-bound drums that people bring with them.

The base of the “mountain” (it’s not very big) is situated right in the city centre, a few blocks above Rue Saint Catherine, just west of the Plateau, and accessible by Mont-Royal Metro.

People come with drums and spread out around the parc, others lay out bracelets and other trinkets for people to buy. They share a flow, and what you wind up with is an amazing atmosphere of hundreds of drums, all in sync, usually to the same pace of a heartbeat.

Sadly, I’ll have to update this post another day with photos of my time there. But truthfully, no photos would do it justice anyway. For more information visit

Montreal Summer Festivals
Photo by Dean Bere

Parc La Fontaine

If I remember correctly, the same bloke who created Manhattan’s Central Park was commissioned to design Parc La Fontaine. It’s designed to be a mini-replica of the former.

It’s right on the base of the Plateau, the French (and best) of the two downtowns Montreal has –yep, one for each culture in this bi-cultural town. It’s accessible on foot from Metro Sherbrooke.

I spent most of my time living in apartments somewhere around this parc and it became my office, my lounge, and a great place to make new friends.

One half is all hills and pond, the other half has an area that’s ideal for soccer and barbecue. Baguettes and blunts as far as the eye can see on either side.

Montreal summer festivals

Montreal Summer Festivals

In a strong finish, I leave you with a list of Montreal summer festivals and how to find more information about each. Even then, I’m only covering the ones I know best. I don’t want to fill your head with a bunch of copy-and-paste blogger repost silliness, I’d like to keep it real.

Montreal summer festivals are unparalleled by any other Canadian city for the sheer amount of time and space they occupy –the City of Montreal lets them take over the entire city, and yet some how, they don’t disrupt the infrastructure.

Even with all the action, people are still able to live their lives and get to work on time. Even protests run on the same precise clockwork, albeit with a little noise pollution.

These are only a handful of the summer festivals I greatly enjoyed personally in my 5+ years in Montreal, although there’s more on this website.

I can personally vouch that each of the following festivals are unbelievably saccharine, and well worth your time:

  • Jazz Festival
  • Beer Festival
  • Fireworks Festival
  • Circus Festival
  • FrancoFolies Festival
  • Food Trucks Festival
  • Folk Festival
  • Grand Prix Weekend (F1)
  • Carifiesta Festival (Carribean Festival)
  • Comic Con
  • Shakespeare in the Park
  • Just for Laughs Comedy Festival
  • Montreal Pride
  • Fringe Fest
  • Osheaga –their version of Coachella, a must-see
  • Heavy MTL
  • Ile Soniq
  • Fantasia International Film Festival

This is where I drop the mic —take that, Canada festival circuit.

Toronto Summer Activities
The late “Honest Ed’s”, a Toronto icon


Toronto is a place tourists love to visit, and one that locals eventually leave for Hamilton due to the high cost of living. It’s a city-wide museum of glass, lights, opulence, hipsters and dog parks. A layered wonderland –a Russian Doll of a city that you can visit hundreds of times and you’ll never see it all.

My best summer memories in Toronto were on the verandas of houses in city blocks since torn down for condos –entire neighborhoods being erased for an obsession with crystal castles.

I enjoyed the local food scene very much, Trinity Park, the festivals and concerts, Toronto Island, and climbing the CN Tower for an autism charity.

It’s a world class city with an amazing public transport system –and it needs it, because it’s so damn big and sprawling. And when it comes to summer activities in Toronto, tourists are spoiled for choice. Just don’t short yourself for time, traffic is a nightmare –less so than LA, but comparable.

Canada Summer
Overshadowing the city like a creeper, the CN Tower –what’s next, a ferris wheel?

CN Tower and Sky Dome (Roger’s Centre)

You can’t visit Toronto without seeing the CN Tower and the Sky Dome (now called the Roger’s Centre) –literally, you can’t not see it from just about anywhere in the city.

For as long as I remember, we had the world’s tallest structure. I think UAE takes that title now, but during my first 20+ years of life I know we had the rep for the world’s tallest building.

It’s status once got challenged in Canada and Calgary tried to beat us –but if you Google the Calgary tower, you’ll see we win the tower envy contest in Canada in spades. I’ve been in that one, too –the equivalent of “is it in yet?”. I got to the top and wondered where the rest of it was.

What to Do in Canada

At the top of the CN Tower, there’s a glass floor which is ideal for inducing panic attacks or throwing up on if you’re scared of heights.

The Sky Dome right beside the tower was also considered progressive at one point in time for being a stadium with a retracting roof that rolls back to reveal the night sky during a Jay’s game.

I’ve had many an elementary school class trip there for the World Indoor Games and the like. Today, it still holds up as one of the best stadiums in the world.

Summer activities Toronto
Photo by Laslovarga

Toronto Island

Montreal has their little tiny island outside the city, and so does Toronto. Ours boasts a nudist area, a place for festivals, a park, and the Billy Bishop airport. All of which are separate enough to ensure that no one bumps into eachother.

Pack a lunch and take a ferry to the island, tourists won’t be disappointed. It’s a great place to unwind, take photos of Toronto from afar, and relax. The sounds of the city dissipate behind the sound of birds and trees that line the island.

Toronto Summer activities
Photo by Simon P

Trinity Bellwoods Park

Trinity Bellwoods is my go-to for killing time on a lazy summer afternoon in Toronto. It’s a large park with a paved jogging/bicycling/rollerblading track that weaves through it, plenty of space to lay down a picnic blanket, an area to let dogs off the leash, and benches to sit up and take it all in.

There’s also a community garden with a greenhouse, a Farmer’s Market, a baseball diamond, and a community centre close enough to use a toilet or refill your water bottle.

You can learn more about Trinity Bellwoods Park here.

Canadian Summer Months Itinerary

Street Graffiti, Sculptures, Galleries and Museums

Toronto’s got plenty of art strewn throughout the city; graffiti on back alley walls in the Queen West area, commercial art lining the streets, and rare collections in art galleries and museums all over the downtown core.

There’s also the Hockey Hall of Fame and Casa Loma –in essence, a “living” museum; a historical building you can explore and learn more about it’s place in Toronto history.

You can learn all about Toronto’s galleries and museums here.

Canada Summer

Key Neighborhoods

While the Annex used to be my personal favorite for cafes during the day, great food and really eclectic night spots, I hear it’s all been converted into glass towers.

However, I checked to see if Tilt was still around, and it appears to be! Score.

Tilt is a vintage arcade and bar located in the Annex that I discovered in April of 2017. It’s like walking into your old best friend’s late 80’s / early 90’s basement, complete with those old kitschy couches everyone had at the time. Pay a cover, play all the classic arcade boxes and consoles until your thumbs cramp up, and drink beer. You can find out where Tilt is by visiting their website (it’s also close to a cannabis dispensary if my memory isn’t too garbled).

My other recommendations for key neighborhoods to visit in Toronto are Queen West (vintage, boutique shopping and graffiti on display), the Kensington area (great vibe, vegan restaurants), St. Lawrence Market (Sunday brunch –Hank’s was my go-to), Parkdale (live music), and the Distillery District (music, history, and beer).

And then of course, there’s plenty of shopping for the “normal” tourist within walking distance of Union Station –a place you will undoubtedly encounter. Upscale shoppers will want to explore Yorkville.

Toronto Summer

Toronto Summer Festivals

Once again, I will list my favourites and drop a link where you can find more information about Toronto’s summer festival lineup:

  • Luminato
  • Fringe
  • Toronto Jazz Festival
  • The CNE —a must if you’ve got kids with you
  • Hot Docs
  • NXNE (North by Northeast)
  • Taste of the Danforth
  • Fan Expo
  • Toronto International Film Festival (TIFF)
  • Buskerfest
  • Nuit Blanche

Summer in Canada

Theme Parks

There’s two classic Greater Toronto theme parks that, in addition to the CNE, are probably a part of every childhood in the region –Canada’s Wonderland and Wet ‘n Wild. One being a theme park, the latter being a water park. They’re not far from one another, and they’re both worth consideration.

Wet ‘n Wild is a little run down, but it’s great if you’re looking to have a pint and enjoy a dip in the pool, lazy river, or hop on any one of its water slides. I used to sell cold beer next to the heated pool –what a gig.

Burlington Summer
Skyway Bridge and Lake Ontario, Burlington


Burlington is a beautifully landscaped, middle-class sleepy suburb outside Toronto that’s known for it’s beautiful waterfront, bangin’ Sound of Music festival, and small boutique shops that line it’s downtown core.

It’s a great place to recover from the hangover of glass and skyscrapers in Toronto; the people are friendly, and the city, as much as they’ve torn down many historic buildings, retains it’s olde-towny feel.

To throw back to Jim Carry a last time in this article –I have a suspicion that Burlington was what he was thinking when he started filming Truman Show. Much of the city is so well-manicured it feels like a movie set.

Canada Itinerary

Sound of Music Festival

This one and only recommendation for my home town is an absolute must if you’re passing through Burlington just before the middle of June when the Sound of Music Festival is on.

It’s a not-for-profit, award-winning festival that puts Burlington on the map, and it’s mostly free with an optional VIP tent and a handful of ticketed gigs. It was a great way to lure friends from far and wide to visit on my birthday, as it seems it’s always running the weekend of.

With Canadian acts like Sloan, Headstones, Blue Rodeo, Finger Eleven, the Tea Party, The Trews, David Wilcox, Tom Cochrane, Junkhouse, Jacksoul, Wintersleep, Great Lake Simmers, Simple Plan, 54 40, Tokyo Police Club, Ashley MacIsaac, and a handful of well-known international acts like Bush, Devo, and Men Without Hats –and those are only the ones I can remember off the top of my head, the Sound of Music Festival is a great way to spend the weekend in Burlington.

You can learn more about the Sound of Music Festival on their website.

Canada Festivals Supercrawl Hamilton
Hamilton, a view from the escarpment


Hamilton is a love story that cities like Detroit and Portland could learn from. It was once known as a bustling jazz town with it’s population a majority of hard working blue collar workers. Each generation finds less blue collar work than the one before it, and as a result it’s had its challenges over my lifetime.

Today it’s the “City of Waterfalls” and a perfect alchemy of former steel town meets present-day medical technology hub with a healthy side of natural beauty and one hell of an active arts scene. The city owes much of its recovery to the latter, as the arts and technology sectors gave the city a much needed second wind.

The world came for the jobs and cheap housing and then stayed for the Art Crawl, killer music scene, and its waterfalls. Hamilton has beautiful green spaces, culture, class, and economy.

Of all the cities on this list I feel some “ownership” when I’m in the Hammer, and I will forever be grateful for the opportunities the city afforded me while living there. It’s a city for underdogs, and even today the potential for greatness hangs thicker in the air than the smoulder of last century’s smoke stacks.

Supercrawl and Other Hamilton Summer Festivals

On the second Friday of every month, James Street in Hamilton’s downtown opens up to host the Art Crawl; a celebration of local arts and culture, food trucks, great busking, and all measure of street performances.

And that was all well and good –until someone thought it would be a great idea to turn it into a bigger phenomenon, taking place once every year during September. And as such, the award-winning Supercrawl was born. An event known as “Canada’s Biggest Party”.

Supercrawl takes over James Street North and surrounding area from King Street to the waterfront, and it’s an Art Crawl on steroids.

Fire dancers, jugglers, buskers, choirs, mimes, illustrators, painters, comedians and food vendors line the street, where in the centre of the road are back to back stages that are host to Canadian and international bands like Broken Social Scene, Dan Mangan, Wintersleep, Blackie and the Rodeo Kings, Sam Roberts, Lights, Junior Boys (above), the Arkells, Dirty Nil, and many others.

It’s one hell of a f*cking party.

Other summer festivals in Hamilton that I’d recommend include; Festival of Friends, Hamilton Film Expo, Fringe Fest and Open Streets.

Hamilton Summer
Source: Dundurn Castle management


Strewn around the city are dozens of other sightseeing gems, divided by an escarpment –a cliff of sorts, making for some great waterfalls, forest areas, water bodies, and historic architecture mixed in for good measure.

If you’re stumped for things to see in Hamilton, you can’t go wrong with the following;

  • Art Gallery of Hamilton
  • Bayfront Park
  • Fifty Point Conservation Area
  • Cootes Paradise (near Burlington’s Royal Botanical Gardens)
  • Dundurn Castle and a really old Gothic cemetery across the road from it
  • Cliffview Falls, Chedoke Falls, Buttermilk Falls, Albion Falls, Tews Falls, Hermitage Falls, Great Falls, Webster’s Falls, Princess Falls, and Scenic Falls –to name a few
  • Canadian Warplane Museum
  • Westfield Heritage Village

Niagara Falls Canada at Night

Niagara Falls

Locals love Niagara-on-the-Lake (NOTL) for it’s wine country vineyards, and tourists love it for the sights, smells, and food that welcome American border crossers with open arms.

Unlike all the other destinations on this list, NOTL is best enjoyed on a weekend and not for a long-term stay.

It’s got the traditional tourist money sucks; a casino, Ripley’s Believe It Or Not and aquarium, Hard Rock Cafe, some great restaurants, and you can ride a ferry below the falls and see them up close.

Canada Summer
Take a ride on The Maid of the Mist to see Niagara Falls up close

Niagara Falls is always a great place to catch your breath. For me, some Tim Horton’s coffee in a paper cup, a pack of cigarettes, and the Falls are all I need here and it’s all I ever plan on going for no matter what season it is.

What’s on Your Great Canadian Road Trip?

Alright, I left some serious meat on the bone in this one. If you’re a local and you think I left out any places to visit in Canada during the summer that absolutely needs to be on this list, I’d love to hear from you in the comments.

I will be updating this post often over the next year or two to include many more Canada summer activities, so check back now and again to see if there’s anything new to see and do in Montreal, Toronto, Burlington, Hamilton, or Niagara Falls.

Places to visit in Canada during the summer

What to do in Canada
Canada summer months

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