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5 Romantic Proposal Ideas in Toronto

by James Kenneth Presley
view of the toronto skyline from the water featuring an orange and yellow sky

Having a hard time coming up with the ideal setting for your Canadian proposal? It’s a big decision—not to mention, overwhelming. That’s why we’ve offered you a little journey through Toronto to help you simplify the process and discover the perfect place to pop the question, one that complements and makes sense for your relationship, no matter the season.

As the capital of the province of Ontario, Toronto’s awe-inspiring skyscrapers will shrink in comparison to the grand gesture of love you’ll soon present to your forever love. From festive outdoor settings to architectural masterpieces, there are tons of proposal idea options in this dynamic metropolis, one with a culture as rich as its history.

Without further ado, here is our roundup of the 5 most romantic proposal ideas in Toronto that are sure to result in a resounding yes—and a kiss.

1. The Toronto Christmas Market

people gather at night under festive twinkle lights at the toronto christmas market

Are those Christmas bells you hear in the distance or wedding bells? The historic Distillery Market, a pedestrian-only area featuring 19th-century buildings and cobblestone pathways, hosts the annual—and supremely festive—Toronto Christmas Market.

Here, you can experience all the sights and sounds of the holidays while taking in this festive Toronto tradition and its offerings, including local musicians and craftsmen, artisanal delicacies, and delicious mulled wine. Whether it’s because of the gala of wood carvings, the handmade holiday ornaments, or the European-style Christmas cocktails, this event will leave you and your sweetheart all warm and fuzzy.

That’s why we think proposing at a place as joyous as Toronto’s Christmas Market will light up your beloved just as bright as its giant Christmas tree. Bonus points if you can arrange some local carolers to sing a holiday classic after your romantic proposal, one that’ll surely blow up your Instagram.

Find The Toronto Christmas Market on Facebook, Instagram, and Twitter.

2. Casa Loma

exterior of casa loma castle under a blue sky in toronto

If it’s a fairytale proposal your love desires, consider taking a trip to Toronto’s Casa Loma, a city-owned heritage landmark that was built in 1914. Located in midtown Toronto, this majestic castle is considered one of North America’s most enchanting attractions, making it an ideal setting for your proposal.

Casa Loma, decorated with a European flair from imported artists, sits on over 343,000 square feet of space and features seven floors of uniquely-themed rooms and suites complemented by 5 acres of lavish gardens.

If you and you sweetheart happen to be movie buffs, you may be excited to learn that Casa Loma has hosted multiple movie shoots, serving as the setting for Hogwarts in Harry Potter and the Deathly Hallows and the beast’s castle in Disney’s 2017 Beauty and the Beast, to name a few. Why not make your special proposal moment one that will be remembered as a tale as old as time?

Find Casa Loma on Facebook, Instagram, and Twitter.

3. Nathan Phillips Square

view of nathan phillips square in toronto featuring water, arches, a large toronto sign, and buildings in the background
Photo: Wikimedia Commons

Named after a former Toronto mayor, Nathan Phillips Square is an urban plaza that forms the forecourt to Toronto City Hall. With over 12 acres where tourists and Toronto locals come together and celebrate the spirit of community, this location plays host to a variety of concerts, rallies, and other ceremonies.

Weekend and seasonal events take place on a recurring basis, so you’ll have countless opportunities to strategize your marriage proposal. Plus, Nathan Phillips Square provides you with an endless playground of opportunities to pop the question. Whether you propose on the elevated concrete walkway or at the square’s Peace Garden, which features a large fountain and a stone-clad gazebo, Nathan Phillips Square has no shortage of romantic options.

One impressive feature is the reflecting pool which rests under three concrete arches and transforms into a large skating rink during the winter months. If it feels right to you, perhaps you can get down on one knee, pull out that ring, and ask your beloved, “Now that our love is on ice, will you marry me?”

Find Nathan Phillips Square on Facebook, Instagram, and Twitter.

4. The CN Tower

view of the cn tower in toronto under a blue, cloudy sky with surrounding buildings

Standing tall and kissing the clouds at 1,815 feet tall, the CN Tower in Downtown Toronto is currently the 9th-tallest freestanding structure in the world. So why not take your love to new heights as you attempt the tower’s EdgeWalk?

As the highest, hands-free walking experience, you and your soon-to-be fiancé can admire views of the city and the Toronto Islands—all from the safety of a harness and a cable apparatus from the tower’s rooftop.

But if EdgeWalk is a bit too extreme for your proposal, consider booking a reservation at the tower’s 360 The Restaurant. Sitting 1,150 feet above the ground, the restaurant offers locally-sourced and market-fresh cuisine options essential to Canada, as well as craft beers and sophisticated wines. With panoramic views of the city and a variety of menu options, you can make your proposal as memorable as your time spent atop one of the true wonders of the world. 

Find the CN Tower on Facebook, Instagram, and Twitter.

5. High Park

two people walking through high park in toronto along a leaf-lined pathway in autumn

Recognized as one of Toronto’s most significant natural sites, High Park is a municipal park that spans 400 acres, offering a variety of recreational activities while reserving a large portion of the park to honor its natural state.

With easy public transit access, this park is a must consider for the active, outdoorsy couple. It offers a variety of hiking trails, sporting facilities, and a gorgeous lakefront for a possible couple’s yoga-in-the-park session. If there are children involved, or you plan to make your proposal a family affair, consider visiting the park’s zoo, a feeless feature of High Park that’s open all year.

One of the biggest draws is the cherry blossoms which are located near the park’s Hillside Gardens and duck pond. These cherry blossoms tend to peak around late-April to early-May for a couple of weeks, depending on the weather. Perhaps the hopeless romantic in you will propose to your love as you say, “Unlike the beautiful cherry blossoms, my love for you will continue to bloom, growing each and every day we spend together. Our love will always be in season.” 

Find High Park on Facebook and Instagram.

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