2019 Toronto Summer Events and Festival Guide

Summer 2019 Toronto Events and Festivals Guide 

There is lots of fun and free events to do in Toronto all summer long. The guide is divided into two sections. 1.) Events listed by date and 2.) Things to do in Toronto that happen all summer long which also includes the list of weekly events at The Bentway.  Most of the festivals are free however some music/alcohol festivals do have an admission fee which is indicated below. We have provided you a short description of the event with links to some of our blog posts from past events to provide you more details. Als

We created this guide because we were unable to find a comprehensive listing of the up-to-date list of summer events and festivals in Toronto. So we created one for you by going to each and every event website to confirm the date and details. Please note that some dates are show as to-be-determined (TBD) because the event organizers have not updated the 2019 dates yet,  however we will update the dates as they become available.

Location and getting there. We have noted the location of the event and how long it takes to get from the Boatel. Don’t worry about the car because you can get to most of these events and festival by walking or streetcar access from Toronto’s only boat B & B but as a reminder please book your Boatel stay early so that you’re not disappointed.

A note to event organizers: if you wish any details updated or if you wish to be included in our guide please email us.

2019 Calendar of Events and Festivals in Toronto this Summer

June 1 – 2, 2019           SING! Toronto Vocal Arts Festival is Canada’s premier a cappella festival (singing without instruments) held every year. 10am to 6pm. Location: Distillery District.  

June 1-2nd, 2019      Riverdale ArtWalk is a fine art exhibition showcasing artists in Jimmie Simpson Park in Queen Street East arts district. 11am to 6pm Free Event

June 7-8, 2019         The Bentway NEW this year –Dérives, a site-specific commission that explores and celebrates the architecture of The Bentway, by acclaimed Canadian choreographer Noémie Lafrance. Free Event

June 7-8, 2019          Dundas West Fest  is a celebration of arts, community and everything local. The festival stretches across 12 city blocks and features 3 stages, 6 busker areas, over 40 patios, and shopping at over 200 different vendors. Free event

June 8, 2019            Toronto Art Crawl hosts over 65 artist and food vendors. Free Event. 11:00am to 6pm Location: Liberty Village Park

June 8, 2019          Toronto Naked Bicycle Ride Once again the naked bike ride takes to the streets of Toronto with a theme of “bare as you dare”. The events starts at 11:00 in the Coronation Park with body painting available. Free event – bring your own bike 

Harbourfront Festivals

June 8-9  2019      Beaches Art & Craft Show  For the 35th year the annual festival is held in Kew Garden Park. This is one of the best arts and craft shows in the city.  Free event. Location: 2075 Queen St. East

June 7-23, 2019          Luminato Toronto is a city wide annual festival of Lights, Arts and Creativity. Free. Location: Multiple locations.

June 7-16, 2019      North By Northeast Music Festival (NXNE) is an annual music and arts festival that showcases 650 bands and 40 films in five exciting days. $ Cost for admission. Location: Multiple locations.

June 8, 2019        Roncy Rocks Music and Art Festival in Roncesvalles Village features an juried art show an sale, music, food and side-walk sale. Free Event: Location: Roncesvalles Village

June 15, 2019         Leslieville Flea at the Distillery District outdoor in the main square. 11:00 to 6pm Free event.

June 14-16, 2019       Taste of Little Italy Is an annual cultural event in the heart of Little Italy with music, street performance and sample food from over 45 restaurants. Free event. Location: Little Italy (College  from Bathurst to Shaw). Take the Spadina Streetcar to College 10 minutes or 25 minute walk from the Boatel.

June 14-16, 2019       Beach BBQ & Brews Festival is an annual event every Father’s day weekend at The Beach. Enjoy Ribfest, live music, children’s play area, craft vendors, grilling demonstrations and beer garden. Great family outing to celebrate Father’s Day. Free Event. Location: Woodbine Park at Coxwell and Queen Street East

June 15-16, 2019        Toronto International Dragon Boat Race Festival in its 31st year with over 200 teams from around the world. Location: Toronto Centre Island 10 minute ride on the TikiTaxi ($10) or walk to the ferry docks.

June 21, 2019         Summer Solstice Cruise – Board the Tall Ship Empire Sandy for a dinner cruise. music and dancing to celebrate the first day of summer. $85 + cash bar. Boarding at 7pm return 10:30. Ask us for more details. 

June 22, 2019         Summer Solstice Festival– This annual festival in celebration of summer is held in this revitalized west end neighbourhood . Includes a side walk sale and entertainment. Free event. Location Dundas Street  between Keele and High Park. 

June 21-23, 2019      Pride Parade Festival celebrates diverse sexual and gender identities with many  events during the 10 day festival including the famous Pride Parade Free Event Location: Gay village Church & Wellesley

June 21-23, 2019       Toronto Craft Beer Festival  will be held at Ontario Place (955 Lake Shore Blvd W, Toronto). 20 minute walk or easy bike ride. 19+ event. 

June 21-30, 2019         TD Canada Trust Jazz Festival celebrates all Jazz musical styles in its annual festival. 1500 musicians and 350 concerts  Location: Main Stage is at Nathan Philips Square (city hall) plus multiple other location

June 28-29, 2019        Queen’s Plate Join the Hats and Horseshow Party at Woodbine Race Track for the annual 160 running the Queens Plate  with live thoroughbred racing . $ for admission Location: Woodbine and Lakeshore Ave

June 30, 2019        Kensington Pedestrian Sundays takes place the last Sunday of the month from May to October. Streets are closed to traffic, vendors expand onto the streets and sidewalks and live music in the heart of the funky Kensington to celebrate the neighbourhood. noon – 7pm. Also includes the Kensington Art Fair which runs  from 12-7PM 

July TBD        Dancing on the Pier every Thursday. Free event Location Harbourfront Centre – 10 minute walk from the Boatel

June 29 to July 1, 2019      Redpath Toronto Waterfront Festival. The annual festival in celebration of Toronto’s vibrant waterfront and this year the Tall Ships are coming to town with the famous BlueNose and 9 other Tall Ships to tour. Free event with tickets $ available to tour the Tall Ships. Location: Queens Quay from Spadina to Jarvis. The Boatel is the best place to stay for this festival

July 2019          Waterfront Artisan Market Every Saturday and Sunday this summer HTO Park will play host to the Waterfront Artisan Market along the Toronto waterfront with arts, locally crafted merchandise and foo vendors.  See our blog post

July 1, 2019      Canada Day Events Celebrate Canada’s birthday. Join us to celebrate the nation’s  birthday with exciting musical performances and activities for the whole family. Events at multiple locations including Harbourfront Centre. Free event. 

July 6-7, 2019     TD Salsa on St. Clair  The 15th annual festival is a 2 day fiesta which includes food, dancing and more  Free event Location: St. Clair Avenue by subway. 

July 7, 2019        The Bentway The Bentway Block Party, a family-friendly day-long celebration, featuring musical acts, art installations, games, food and drink, and more.  Free Event a short walk from the Boatel.

July 3-14, 2019            The Fringe: Toronto’s Theatre Festival. The largest theatre festival of its kind with 160+ shows in 45 venues with more than 1100 performances featuring local and International theater companies over 12 days. Max ticket price is $13 so that everyone can enjoy theater. Multiple locations

July 5-7, 2019     Sounds of Leslieville & Riverside – part of the Beaches International Jazz Festival  Free event Location: Jimmie Simpson Park @ Queen Street East and West of Logan avenue. Take Queen Street car.

July 5-28, 2019         Beaches International Jazz Festival – free annual music festival features a mixture of Latin, soul, and traditional jazz with more than 100 bands.  Free event every weekend in July. Location: The Beach. 

July 5-21, 2019         Summerlicious  Once again features over 200 Toronto restaurants that offer three-course prix fixe lunch and dinner menus at exceptional price points. Reservations recommended. Various locations.

July TBD              Harbourfront Centre Free Flicks presented by Billy Bishop Toronto Airport every Wednesday at the outdoor theatre. Free Location: Harbourfront Centre just a 10 minute walk from the Boatel.

July 11- August 3, 2019         Summer Music Festival explores and celebrates cross-cultural influences of classical music from the times of Mozart and Mahler, right up to the composers of today. Ticketed $ event. Location: Various locations.

July 12-14, 2019         Toronto Outdoor Art Exhibition Since 1960 this an annual outdoor exhibition has been held at Toronto City Hall. A juried exhibition with 500+ artists.  Free event. Location: Nathan Phillips Square at Queen & Bay streets.

July 12-14, 2019        Honda Indy Toronto returns to the streets of Toronto around Exhibition Place with world class Indy Car racing. $ for admission. Location: Exhibition Place Lakeshore Avenue and Strachan. 20 minute walk or 10 minute streetcar ride 

July 20, 2019        Leslieville Flea at the Distillery District outdoor features antique, food and artisan market in the main square. 11:00 to 6pm Free event

July 20, 2019         Empire Sandy Blues Cruise – A wonderful evening cruise aboard the Tall Ship Empire Sandy with live blues band, buffet dinner and cash bar. Boards  7:00pm & Returns 10:30pm. $ event – ask us for details. Location: Empire Sandy

July 20-21, 2019     Toronto Triathlon – this annual event brings athletics from across North America to compete in this event. Held at Marilyn Bell Park on Lakeshore Blvd. 

July 18-21, 2019         Toronto Burlesque Festival this annual festival returns with workshops to learn from international stars, art reception, and the famous burlesque ball to celebrate this classic art form. Location: Revival Bar and Virgin Mobile Mod Club.

July 26-28, 2019       Toronto’s Festival of Beer returns with 200 brands of beer and 60 brewing experts from around the world. Hosted by the Beer Store. Ticketed event. Location: Exhibition Place at Lakeshore and Strachan. 20 minute walk or 10 minute streetcar ride from the Boatel. See our blog post

July 25-August 4, 2019    Festival Kompa Zouk is Ontario’s largest gathering of French-Caribbean performers celebrating culture through dance, music and cuisine. Location: David Pecaut Square on King Street. 

July 27, 2019        Kensington Pedestrian Sundays takes place the last Sunday of the month from May to October. Streets are closed to traffic, vendors expand onto the streets and sidewalks and live music in the heart of the funky Kensington to celebrate the neighbourhood. noon – 7pm. Also includes Kensington Art Fair which runs 12-7PM

July 27, 2019         Taste of the Middle East – celebrate of food, dance and culture of the Middle East. Location: Yonge Dundas Square. 20 minute walk or street car/Subway to Dundas Station. Free Event

August 3, 2019              Scotiabank Caribbean Carnival Toronto Parade (formerly Caribana). The highlight of this annual three week festival is the famous Grand Parade  with Calypso, Steel Pan, Brass Bans, Soca and Reggae and Caribbean styled dancers. Location: Exhibition Place and along Lakeshore  20 minute walk or streetcar

August TBD                      Harbourfront Centre Free Flicks presented by Billy Bishop Toronto Airport every Wednesday. Free Location: Harbourfront Centre outdoor theatre just a 10 minute walk from the Boatel.

August TBD         Dancing on the Pier every Thursday – Free Location Harbourfront Centre – 10 minute walk from the Boatel

August 2-4, 2019       Island Soul Festival at Harbourfront Centre Come to the waterfront to catch a little bit of that island soul and experience the rich legacy of Caribbean music heard through Canada and around the world.

August 2-11, 2019         Rogers Cup – Tennis anyone? This prestigious professional tennis tournament is organized by Tennis Canada and presented by National Bank and attracts the top ranked tennis players from around the world. This year the men will be in Toronto while the women will play in Montreal at the same time. $ for admission. Location: Rexall Centre at York University. Drive or 1 hour by public transit.

August 9-11, 2019       Krinos Taste of the Danforth celebrate Greek food, music, art and culture at the largest Greek Festival in North America. Free event. Location: Greektown on Danforth Avenue. Street car to subway.

 August TBD               Sail-In Cinema is hosted by Ports Toronto and is the world’s first two-sided floating movie experience. Movies are shown under the open skies on a two-sided screen set atop a barge in Toronto Harbour. You can watch movies for free by boat if you drop anchor in Toronto Harbour or landlubber can bring a chair or blanket. Free event. Location: Sugar Beach Queens Quay and Jarvis. 20 minute walk from the Boatel along Queens Quay.

August 16-Sept 2, 2019      Canadian National Exhibition (CNE). Since 1879 the CNE or the EX (as locals call it) is Canada’s largest community fair. Includes daily parades, talent shows, air show, free concerts, ice skating show, talent competition, midway, beer garden, rib fest, discount shopping, food vendor galore and a working farm. $ cost for admission TIP: $6 after 5pm Monday – Thursday.  Location: Exhibition Place at Lakeshore and Strachan. 20 minute walk or 10 minute streetcar ride from the Boatel. See our blog post

August 17, 2019        Leslieville Flea at the Distillery District outdoor in the main square. 11:00 to 6pm Free event.

August 22-25 2019       Fan Expo Canada Four days of celebrity guests and exciting family-friendly events await at Fan Expo Canada. Ticketed Event

August TBD    Coconut Festival will host its annual event for health conscious foodies with a love of all things coconut. The events includes stage presentation, dance interactive demonstrations, yoga along with vendors promoting healthy products and coconut based foods. Free event Location: David Pecaut Square 215 King Street West, 20 minute walk or 10 minute bike ride.

August 25, 2019       Kensington Pedestrian Sundays takes place the last Sunday of the month from May to October. Streets are closed to traffic, vendors expand onto the streets and sidewalks and live music in the heart of the funky Kensington to celebrate the neighbourhood.  Sundays from  May – September,  noon – 7pm

chinatown festival 2August TBD                Chinatown Festival Immerse yourself in this Asian festival which annually hosts a street party in the heart of Chinatown on Spadina street. The festival features mixed martial arts demonstration, lion and dragon dances, multicultural performances and international cuisines. Free event.  Location: Spadina Avenue a 20 minute walk from the Boatel or 7 minute streetcar ride.  See our blog post

August 30th to September 2, 2019          Scotiabank Buskerfest is the largest international street performance festival in North America with over 170 of the best street performers from Canada and around the world from daredevils, puppeteers, contortionists, clowns, music, magicians and more. $ Admission is a donation to Epilepsy Canada Each performer then passes a hat after their performance. Location: Woodbine Park

August 31 – Sept 2, 2019       Artfest 2019  Fall Fine Art and Craft Festival is an outdoor art and craft shows celebrating painting, photography, sculpture, fine craft, live music. Location: Set throughout the cobblestone lanes of the Distillery District. Free admission 

August 31 – Sept 2, 2019        Canadian International Air Show with it’s dazzling array Toronto air showof planes from around the world and Canada’s very own Snow Birds. Shows daily. Location: can be viewed from the Boatel however there are various locations along the waterfront or Toronto Island that provide an unobstructed view. Various Toronto charter boat also offer public cruises during the airshow.  See our blog post.

September 5-15, 2019           Toronto International Film Festival (TIFF) attracts Hollywood actors and visitors at this special annual event hosting more than 300 films from over 60 countries. $ cost for admission. Location: Various locations.

September 7-8, 2019           Cabbagetown Art and Crafts Sale is one of the premier art and craft festivals with unique made-in-Canada artisans and is held each year during the Cabbagetown Festival and Riverdale Farm Fall Festival. Location: Riverdale Park West, in the heart of Toronto’s historic Cabbagetown. Free event Hours Friday 1-7pm and Sat /Sun 10am to 6pm

September 7-8, 2019              Toronto Vegetarian Food Fair has over 100 exhibitors which includes food, wellness, health and authors. Location: Harbourfront Centre Queens Quay Ten minute walk from the Boatel.

September TBD      Toronto Bicycle Music Festival is a yearly series (since 2010) of free outdoor pedal-powered concerts taking place in and between our city’s great community parks and streets. Location: Making music and travelling across the city from *to be determined* to Prairie Drive Park.

September 13-15, 2019          Toronto Ukrainian Festival Bloor West Village closes down it streets to cars to celebrate North Americas largest Ukrainian festival. The festival features a parade, dance competitions, food and music celebrating Ukrainian culture. Free event. Location: Bloor West Village between Runnymede and Jane Streets.  Take the streetcar to the subway and get off at Runnymede Subway approx. 30 minutes See our blog post

September 13-15, 2019          Toronto Polish Festival  Annually Roncesvalles Village closes down the street to celebrate North Americans largest Polish festival featuring sidewalk sale, dance competitions, Polish food, music and culture. Free event. Location: South of Bloor and Dundas West in Roncesvalles Village. 

September 22, 2019        Word of the Street Book and Magazine Festival is a not-for-profit which promotes Canadian reading and writing through this free outdoor festival and has Canada’s biggest outdoor bookstore. Location: Harbourfront Centre – Queens Quay. Ten minute walk from the Boatel.

September 21-22, 2019      Queen Street Art Crawl The main draw is the Outdoor Art Show & Sale which features 250 artists, food vendors, community booths and an entertainment stage. The event also includes The Parkdale Night Crawl and Parkdale Crawl, a walking tour with guest speakers. Free event.  Location: Trinity Bellwoods Park on Queen Street West and Parkdale various locations Walk 25 minutes or Bike share

September 20-29, 2019           Francophonie en Fête  The annual Toronto Francophone Music Festival, a jam-packed 10-day deep dive into the rich Francophone musical diversity that thrives in Toronto. A highlight of the Festival is the Free Distillery Weekend Concerts on September 21 and 22nd. 

September 29, 2019        Kensington Pedestrian Sundays takes place the last Sunday of the month from May to October. Streets are closed to traffic, vendors expand onto the streets and sidewalks and live music in the heart of the funky Kensington to celebrate the neighbourhood. Sundays from  May – September,  noon – 7pm

September TBD         Toronto’s JFL42 Comedy Festival includes a stunning array of comedians across North America. Location: various venues



Brand NEW at The Bentway this summer:

May 11-August 30: New Monuments for New Cities, a joint touring art exhibition with the High Line Network, showcasing provocative works by 25 acclaimed artists from Toronto, Houston, Austin, Chicago, and New York that explore new monuments for today’s changing social and political landscape.

June 13-August 29: Recreational classes, including Tai Chi with Eti Greenberg Monday at 5:30 and Thursday at 11:00am and Yoga with Tribe Fitness on Sundays from 7 to 8 pm.

June 13-August 29: Communal Table, will offer weekly communal dining opportunities for neighbours and community members featuring local chefs and food offerings as curated by Toronto restaurant and innovative “culinary talent showcase” The Depanneur to explore Toronto’s diverse culinary traditions. Pre-registration is required.

July 7- August 25: Sunday Social with the Exclaim! Stage featuring Toronto’s hottest musical acts on the coolest covered patio in town at The Bentway from Noon to 9pm. Free event. 

June – October          Waterfront Artisan Market Every Saturday this summer HTO Park will play host to the Waterfront Artisan Market along the Toronto waterfront with arts, locally crafted merchandise and foo vendors.  See our blog post

June to September           Harbourfront Centre Dancing on the Pier every Thursday night during the summer with free live bands, social dance clubs and instructors. Come dance the night away. Location: Harbourfront Centre Queens Quay and York. See our blog post and detailed weekly information above.

June – August             Harbourfront Centre Free Flicks on Wednesdays at sunset with a cooling breeze near the lake and under the stars. Arrive early for a good seat because seating is limited Location: Harbourfront Centre Queens Quay and York.  See our blog post  Detailed schedule above

June  to September      Toronto Music Garden free concerts in a truly magical setting. Most Thursdays at 7pm and Sundays at 4pm and are approximately one hour in length. Limited bench seating is available but very limited so just ask us for a chair or a blanket. Location: Just down the pier from the Boatel. See our blog post

Yonge Dundas Square Lunchtime Live at Yonge Dundas Square Free concerts on Mondays from 12:30 to 1:30 at Yonge Dundas Square. Singer & Songwriter Series Location: Yonge and Dundas.

Yonge Dundas Square Indie Fridays on Fridays from 8-10pm at Yonge Dundas Square. Free music concerts and Beer Garden provided by the Hard Rock Café from 4 to 11pm Location: Yonge and Dundas.

Yonge Dundas Square City Cinema  Free outdoor movies on Tuesdays at sunset. Seating is limited so go early for a great seat. This year’s theme: TBD.  Location: Yonge and Dundas.

Kensington Pedestrian Sundays takes place the last Sunday of the month from May to October. Streets are closed to traffic, vendors expand onto the streets and sidewalks and live music in the heart of the funky Kensington
Sundays from  May – September,  noon – 5pm

Distillery District Sunday Market. Features local artisan goods, including tasty treats like empanadas and organic maple syrup. Free event. Noon till 5pm 

Shakespeare in High Park Bring a blanket and a jacket to enjoy this Shakespeare production under the stars. $ Donation requested Location: High Park located south of Bloor and High Park Ave.

Antique Market at St. Lawrence Market – The Sunday Market is a weekly antiques and collectibles show and sale that takes place every Sunday at the North Market. 

This entry was posted in Events and Festivals, What to do in Toronto by Diane Greene. Bookmark the permalink.

About Diane Greene

Diane Greene stepped off the corporate treadmill in 2004 for pursue a life of traveling and adventure. 10 years later she is still operating Toronto's only Boat Bed and Breakfast and travelling with her husband on Boatel, their 65 foot trawler in the US and Bahamas during the winter. Diane has three wonderful children and 3 grandbabies. Diane loves photography, travel and scuba diving.

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