2019 Toronto Summer Weekend Report

News flash! Summer is just around the corner. If escaping to a cottage every weekend isn’t in the cards for you there is a myriad of events and festivals taking place all over the city of Toronto (and bonus - you can avoid sitting in hours of highway traffic!) Below is your Toronto Summer Weekender Report, a list of events, festivals, markets, shows, and so much more. Now is the perfect time to plan some weekend activities. Rally your squad and make some unforgettable memories this summer without travelling far. Click on the event name for all the details and ticket purchasing if applicable.

June 21- june 23

Pride Parade | June 23 | Church Street |

Celebrate diversity with over 1 million people as the parade marches from Church Street and Bloor Street all the way down Yonge Street to Yonge and Dundas Square. Although the iconic parade is often considered the main event, there are heaps of pride activities planned this weekend in Toronto’s Village.

Toronto Craft Beer Festival | June 21 – June 23 | Ontario Place |

This weekend join other beer lovers and celebrate Toronto’s independent craft brewers of beer and cider while enjoying delicious food, fun activities and live music. Catch this event at Ontario Place. Early Bird Packages are on sale now!

June 28- July 1

Queen’s Plate Festival | June 29 | Woodbine Racetrack |

Grab your fascinator and celebrate 160 years of the Queen’s Plate Festival while enjoying thoroughbred horse racing, gaming, live entertainment and mingle with Toronto’s best dressed. You will need to purchase tickets to the horse racing event that takes place on

Canada Day Celebrations | July 1 | Multiple Locations Toronto Wide |

Celebrate Canada’s Birthday! With a wide range of activities taking place this weekend

there is no shortage of ways to show your pride. Every year a spectacular fireworks show can be seen at Ashbridges Bay and Woodbine Park in Toronto’s Beaches. A full schedule of activities will be available in June, so be sure to check back here for all the details.

July 5 - july 7

Wine Fest | July 5 – July 6 | CF Shops of Don Mills |

Calling all wine lovers! This is Toronto’s first ever outdoor wine festival! Hooray! Located at the CF Shops of Don Mills, this two-day event will host several free workshops, activations geared towards wine activists and present the Best Wine awards. Sip and sample old favourites and discover new wines or simply enjoy the live music and fine fare.

July 12 - July 14

Honda Indy Toronto | July 12 – July 14 | Exhibition Place |

This world-class motorsport festival takes place on the Toronto streets surrounding Exhibition Place near Lake Ontario and downtown Toronto. The Toronto Indy features beer gardens, food trucks, interactive displays, activities as well as charity events. Even if you don’t plan on attending this event, chances are you will hear these Indy cars zipping around the city this weekend!

58th Toronto Outdoor Art Fair | July 12 – July 14 | Nathan Phillis Square |

Discover over 360 artists and creative minds during this one of a kind outdoor art festival. Check out the full roster of artists who will be showing at this weekend long event and check out the Jurors top picks! This event is great if you are interested in supporting local artists and talent and connecting in a personal setting.

July 19- July 21

Burlesque Festival | July 18 – July 21 | Revival Bar & Virgin Mobile Mod Club |

Toronto’s Burlesque scene has flourished into a diverse fierce team of talent. The 12th annual Burlesque Festival is compiled of several performances and parties that are sure to be entertaining and whimsical. If you haven’t had a chance to get acquainted with burlesque, this is the perfect opportunity to get your feet wet.

Toronto Triathlon Festival | Sunday July 21 | Toronto Wide |

It’s not too late to register! But if checking a triathlon off your bucket list isn’t a top priority for you this summer, don’t fret. You can show your support by cheering on the participants from the side line as they run, bike and swim all over the city. This uniquely urban race on the downtown highways is truly a test of human endurance and tenacity.

July 26 - July 28

Toronto’s Festival of Beer | July 26 – July 28 | Exhibition Place |

Celebrate Canada’s broad brewing history and rub elbows with some of the world’s most

notorious brewers at this beer festival. And beer isn’t the only thing on tap at this festival, enjoy headlining acts, great food and much much more!

Jazz Fest | July 25 – July 28 | Toronto Beaches |

Although Jazz Fest technically begins on July 5th, this final week is where many would argue the real action takes place. Enjoy the street festival spanning 2.5km on Queen Street East with over 45 bands playing from 7pm-11pm nightly as well as food trucks, pop-up shops and more. The sounds of big band, jazz, blues, reggae, Latin, African, rhythm and blues will fill the streets this weekend.

August 2 - August 4

Veld Music Festival | Aug 3 - Aug 4 | Downsview Park |

Veld has quickly made a great reputation as one of the best music festivals in Toronto. For two days over 30 dance music and hip-hop artists will take the stage and headliners this summer include Cardi B, Kygo, Skrillex & Tiesto. You will need to purchase tickets in advance for this one.

Caribana | Aug 1 – Aug 3 | Exhibition Place & Lakeshore West |

Caribana is currently North America’s largest cultural festival celebrating freedom, diversity and joy. Expect tourists from all over to enter the city for this feel-good festival. Although this festival has events spanning over 4 weeks, you can catch the grand parade with over the top costumes on August 3rd.

August 9 - August 11

Rogers Cup | Aug 3 – Sunday Aug 11 | York University |

The women’s tennis tournament wraps up this weekend in Montreal and Toronto. See three-time champion Serena Williams and Mississauga’s teenage tennis star Bianca Andreescu among many other women tennis sensations. Catch all the action at the Aviva Centre located on the York University campus.

Taste of the Danforth | Aug 9 – Aug 11 | Danforth Ave & Pape Ave |

This weekend long event incorporates all things Greek, but they boast that there is something for everyone. During the Taste of the Danforth street festival you are encouraged to indulge in food, wine, music, art and culture at the largest Greek Festival in North America.

August 16 - August 18

The CNE | Aug 16 – Sept 2 | Exhibition Place |

Let’s Go to the Ex! The Canadian National Exhibition (CNE) opens this weekend and runs until labour day weekend. This is Canada’s largest community fair and a summer staple for tourists and locals alike. Enjoy free concerts, the air show, the midway, rib fest, discount shopping and of course carnival rides for the entire family. Advance tickets are on sale now.

August 23 - August 25

Toronto Cider Festival | Aug 23 – Aug 24 | Sherbourne Common |

Boasting the best cider party in the city, cider fanatics will not want to miss this award-winning milestone event! Who doesn’t enjoy a cold cider on a hot day in August? And did I mention they have more than 100 kinds to choose from? They also have contests, food, entertainment and interactive games. Day and night session tickets are available for purchase.

August 30 - September 2

Toronto International BuskerFest for Epilepsy | Aug 30 – Sept 2 | Woodbine Park |

With seven stages and a packed schedule of unique performers there is sure to be something that will wet your whistle at BuskerFest. They’ve also partnered up with the Mac n’ Cheese festival this year to bring you the best in comfort food. If it’s relaxation you’re after, you can make your way to the beer tent! Check out the website for the full performance schedule.

Canadian International Air Show | Aug 31 – Sept 2 | The Canadian National Exhibition |

Catch the famous snow birds and airplanes from all the world grace the sky in a one of a kind air show. The air show can be seen from several locations all over the city, including the CNE grounds, waterfront or Toronto Island.

Featured Posts
Recent Posts
Search By Tags
Follow Us
  • LinkedIn Social Icon
  • Instagram - Black Circle
  • Facebook Basic Square
  • Twitter Basic Square
  • Black LinkedIn Icon
  • Black Instagram Icon

O 416-925-9191 | C 416-561-3309josh@chestnutpark.com

1300 Yonge St Suite 100, Toronto