Exciting Events and Date Ideas Happening around Toronto This June

We have rounded up all the best date ideas happening in June for you to keep handy!

Enter, summer dates! While the sun has been shining for a bit now, something about June makes it really feel like the summer. Patios, hikes, days by the water, and endless events and festivals are here, and you’ll seldom find a day without fun date ideas happening in June around Toronto and the GTA.

We have rounded up all the best date ideas happening in June for you to keep handy!

Ongoing Date Ideas

Dine Outdoors at Casa Loma Gardens

If you’ve been counting down the days to dine in a castle-like garden and feel like royalty, the gardens at Casa Loma are open for dining starting June 2nd!

Reservations are highly recommended and are open during operating house (except when they have private events).

Get yourself booked in before they fill up and have the dreamiest date in town!

Ripley’s Aquarium Friday Night Jazz

Jazz nights are back at Ripley’s Aquarium every second Friday of the month! A regular trip to Ripley’s is already a great date idea, but add live jazz music and bars all around the venue and you have the perfect night!

Celebrate an anniversary or special occasion, or make date night a special occasion and dress up for this cute spot.

June 10th

Canadian Music Week

Running from June 6-11th, Canadian Music Week is a celebration of talent and music all throughout Toronto. Now in its 40th year, the Canadian Music Week Festival has featured some of the top headliners in the music industry alongside thousands of rising new artists, including Post Malone, Katy Perry, Ellie Goulding, City and Colour, The 1975, Arcade Fire, Bloc Party, Janelle Monae, Travi$ Scott and so much more.

This year, you can expect Rock, Hip Hop, EDM, Alternative, and Indie Rock in-person concerts, panel discussions, thought leadership, and virtual events!

Sound of Music Festival in Burlington

The Sound of Music Festival is a staple in Burlington and celebrates live music that can be heard throughout downtown Burlington for nine days straight (from June 11th-19th this year).

From the ticketed kick-off concert, Live on the Lake on June 11th at Spencer Smith Park ft. Three Days Grace, Tim Hicks, The Beaches, and Saving Abel; to the huge lineup of FREE concerts on three stages, this is going to be an amazing month for music.

Also happening is the Downtown Streetfest, Grande Festival Parade, midway, vendors, food trucks and more!

June 3-5th, 2022

Do West Fest

Formerly known as the Dundas West Fest, the newly-named festival celebrates the best of Little Portugal with its annual block party stretching along Dundas Street West from Ossington Avenue to Lansdowne Avenue.

The weekend-long, 12-block street festival is closed off to traffic– allowing pedestrians to roam the busy streets and enjoy food trucks, an outdoor fair, live music, and extended patios! It’s totally free to attend but bring some cash if you want to sample the best of Little Portugal’s food, drinks, and artisan vendors! 

June 3-5th

Ajax Rotary Ribfest

We love when in-person events come back! The walk-up Ajax Rotary Ribfest support local and International charities and non-profits while dishing up amazing BBQ from six amazing Ribbers. You can also visit numerous vendors, listen to live music with a drink from Brock Street Brewery, or climb aboard several rides at the family friendly on-site carnival.

June 3-5th

Ajax Downs Casino

Pride Month Kickoff Party at Stackt Market

Over the month of June, stackt will be celebrating Pride Month through a wide array of epic programming, events, art installations, and musical performances celebrating Toronto’s 2SLGBTQ+ community!

On June 4th, you can attend the Pride Month Kickoff Party for FREE. Dance, play lawn games, check out art installations, listen to live DJs, shop at the vendor market and have fun at this all-day party!

June 4th, 2022

June 10-12th, 2022

TD Salsa in Toronto

Canada’s Largest Latin Culture celebration is back this summer! We can’t wait for this festival to take over midtown Toronto and transform St. Clair West into Canada’s biggest salsa party.

What you can expect? Music, dance, visual arts, and culture with salsa dance parties, art exhibitions, and FREE dance lessons at various schools across the city. Get moving with your date!

June 9-10th

Foodalicious Food Festival

Head to Downsview Park this weekend for the best foodie date ever! The Foodalicious Festival is full of good food, a Craft Ceer village, live music, photo ops, and a midway.

Food truck vendors include: The Smoke Stop, Ontario Corn Roasters, Mustache Burger, Summertime Lemonade, Pancho’s Baker, Universal Caribbean Fusion and more.

You and your date can even sign up for a Mixology class at the festival and get those date night drinks stirring!

June 10-12th

Milton Rib and Beer Fest

The Rib & Craft Beer Fest is touching down in Milton this weekend and will feature some of the best rib teams in Canada along with bbq foods along with amazing craft beer vendors! This is a FREE date idea, so you and yours can enjoy live music (Country Night, Rock the Park, and Music Mash Up), giant yard games, kids zones, and classic carnival eats & treats

June 10-12th

Bowmanville Rockin’ Ribs & Brews

Rib Fests are back no matter which city you’re in! Head out to Bowmanville for this exciting weekend for fun, food, beer, music, and all the excitement that comes with delicious food festival dates. 

This amazing community event raises funds on behalf of the Rotary Club of Bowmanville.

June 10-12th

Annual Peony Festival in Oshawa

See gorgeous peonies at Oshawa Valley Botanical Gardens. The popular festival celebrates horticulture, arts and heritage with more than 300 Peony plants in glorious bloom in the gardens.

This festival features one of Canada’s largest contemporary peony collections; the Matsuyama Bonsai Society annual show; Garden-inspired works by painters, sculptors and artisans; Musical entertainment and cultural performances; food from local restaurants; and a photo and art contest!

June 11-12th


Toronto Taste at Evergreen Brickworks

If food is your love language, Toronto Taste has the perfect date night for you! Whether you and your other half are foodies, or just looking to explore and try new things around the city, check out Toronto Taste. The event is presented by The Daniels Corporation and hosted by gastronaut Bob Blumer and on-air chef Bianca Osbourne.

Celebrate at the historic Evergreen Brick Works with food and drinks from 50 of the most recognized and highly acclaimed culinary and cocktail experts together in one spot.

June 12th

June 17-19th, 2022

The Taco Fest

After two years of doom and gloom, what could be better than a weekend-long taco party? Taco Fest returns to Ontario Place.

The three-day fiesta for taco aficionados features over 100 varieties of tacos, not to mention the ever-flowing tequila, salsa dancers, and live mariachi band all in the sunshine– it’s wrapping up to be an unforgettable experience so don’t miss out on the taco the town!

June 17-19th

Taste of Little Italy

The massive weekend festival will transform the heart of Little Italy into a bustling street festival. Taste of Little Italy is an opportunity to capture and explore the tastes and sounds of Italy as College Street transforms into a classic Italian piazza!

From restaurants and street vendors to the myriad of free tastings and samples, you and your date will have an absolute blast.

June 17-19th

Brampton Rib & Beer Fest

Those in Brampton will experience the Northern Heat Series Rib & Beer Festival. You and your date will experience mouth watering, feel-good barbecue and a Beer Market featuring the top brewers from across Ontario!

Entertainment will light up the night with Country Night on Friday, Rock the Park on Saturday, and Music Mash-Up and Ribs on Sunday. Other than ribs, you’ll find brisket, BBQ chicken, cornbread, funnel cakes, blooming onions, ice cream, lemonade and so much more.

June 17-18th

Vaughan Pizza Fest

Pizza lovers, rejoice! If you’ve been waiting for the perfect pizza-loving date, you’ll be delighted to know that Vaughan Pizza Fest is back. They have an amazing line-up for entertainment, and a list of pizzerias that you’ll have to wait a little longer to find out!

June 17-19th

Mac and Cheese Festival by Street Eats Market

The team at Street Eats Market is bringing some delicious foodie festivals and events to Scarborough Town Centre, but we can agree that we’re most excited for the Mac and Cheese Fest.

Grab your date and find so many new favourite mac and cheese creations by local chefs and food trucks!

June 17-19th

June 24-26th

Pride Festival Weekend

Pride Toronto is making their in-person return with the events we know and love, and new exciting additions! You and your date, fam, or friends can experience the classic parade, The Fierce & The Reckless Pride 2022 Kick-Off Party and Mini-Ball at El Mocambo, Cabana Pool Party with Symone, Sober Pride, Trans Pride, Bi Pride, and so much more.

June 24-26th

Toronto Craft Beerfest

If your date just can’t be without a frosty IPA, check out the Toronto Craft Beer Festival at Ontario Place. With over 40 beer brands, it’s Canada’s largest celebration of craft beer. There will be live music and DJs, plus every ticket gets you five sample tokens so you and your date can explore the hoppiest place on earth!

June 24-26th

Taste of Asia Festival

Taste of Asia is Canada’s largest Asian festival celebrating harmony, cuisine and culture for the past 17 years. This year, they’ll be celebrating collaboration with Hakka World Conference and Asialicious to help event-goers understand the various ethnocultural groups.

Check out the video below for everything you can expect at a Taste of Asia datenight!

June 24-26th

TD Toronto Jazz Festival

Now in its 35th year, the TD Toronto Jazz Festival is back this year, showcasing the best performers from across Canada and around the world! They will have 10 full days of outdoor programming to enjoy and is a perfect date ideas for music lovers.

Check out the 2022 programming below!

June 24-July 3rd

We have more local, national, and travel date ideas waiting for you to plan your summer, plus don’t forget to take the datenight game along, and receive Free Shipping when you use DATENIGHT at checkout!

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