9 Places to Spend the Perfect Summer Night in Toronto

There’s no better time to take full advantage of Toronto and all of its food, art, and lake-filled offerings than in the summer months.

There’s something distinctly memorable about summer nights in the city, and a reason why we tell our out-of-town friends to wait until the snow melts to visit.

Here are 9 places to spend the perfect summer evening in Toronto.

High Park
Both seasoned theatregoers and Shakespeare newbies can appreciate the appeal of ‘Shakespeare in the Park.’ For its 34th season, Canadian Stage once again hits High Park to present both Hamlet and All’s Well That Ends Well on alternating evenings throughout the summer. The best part about the outdoor venue is that you can enjoy a picnic and lay back and lounge in a way you can’t in a theatre. If you’re in the market for a ‘date night’ option, All’s Well That Ends Well is one of Shakespeare’s more romantic works. The performances run June 30-September 4.


Photo: Canadian Stage

Bar Reyna
If you’re looking for a laid-back yet refined evening of sharable Mediterranean snacks and quality cocktails, hit Yorkville’s brand new, much buzzed-about Bar Reyna. Aside from the artistic (and addictive) culinary offerings and fit-for-royalty drinks (Reyna means queen), one of the best parts about the space is its breezy back patio, which is tucked away from the street. Offering a tranquil escape from the sometimes over-the-top (but refreshingly revitalized) Yorkville scene, Bar Reyna is perfect for both first dates and quality catch-ups with friends (and a slight hangover that’s totally worth it).

Union Summer 2016
Union Summer returns once again in all of its foodie-filled glory. Transforming Front Street’s Sir John A. Macdonald Plaza, Union Summer will offer 70 straight days of food, drink and entertainment with an extensive outdoor market. If you’re the type with trouble deciding on restaurant options, the market’s 20 anchor vendors – some of the city’s finest – offer a bit of everything.

Vendors include favourites like Carbon Bar, Urban Herbivore, Burger’s Priest, Momofuku and True True Pizza. Naturally, you’ll also find classic cocktails, craft beers, and local wines. P & L Catering will operate a licensed area from Thursdays to Sundays, noon to 9pm, every week. On Wednesday nights, you can stay for their free movies, which will begin at 9pm. Union Summer runs June 27-September 5.

Photo: Toronto Union

The Drake Sky Yard
The Drake Hotel makes a solid option year-round, but the multi-faceted Queen West spot is made even better when their rooftop Sky Yard fills with an eclectic mix of the city’s finest. The newly designed urban oasis transports guests to mid-century Palm Springs, and features cool new additions like a Prince-inspired mural by internationally celebrated artist INSA, art from award-winning Canadian artist Micah Lexier, vintage photos, a retro diving board, and a re-envisioned bar. Of course, the spot features an expertly curated cocktail menu and a unique locally sourced menu.


The Molson Amphitheatre
You can’t go through an entire Toronto summer without taking in a concert at the Molson Amphitheatre. With the setting sun to the west as a backdrop, the breezy concert venue offers the best summertime spot to catch your favourite artists. City and Colour, Gwen Stefani, Blue Rodeo, Snoop Dogg and Wiz Khalifa, and Dave Matthews (as always) are just some of the acts to grace the stage this summer.

Photo: Black Muddy Blog

Sugar Beach
If you live in the city core, hitting the Toronto Beaches can be quite the mission – especially on a weeknight. But too many people forget about the ‘hidden gem’ that is Sugar Beach, an urban beach right at the foot of Lower Jarvis and Queens Quay. Dotted with pink umbrellas and white Muskoka chairs, with both the sailboats and cityscape in the background, it makes for a perfect spot for quality conversation and enjoying the often-neglected Toronto waterfront. Best of all, an evening spent here won’t cut into your summer music festival or road trip fund – it’s totally free.’

Photo: Wikimedia Commons

The Toronto Islands
If you live in Toronto, at least one evening spent on the Toronto Islands is pretty much mandatory. You can either hit the ferry or water taxi and curate your own evening with everything from a picnic dinner on one of the beaches and a mission through the maze, to a meal at The Island Cafe or The Rectory Cafe. If electronic music and a mass gathering of energy is your thing, Electric Island returns next on Canada Day, then each holiday Monday for the rest of the summer. Whatever you do, one thing is certain: you’ll return home with a camera full of stunning, social media-worthy skyline shots.

Photo: Green Autumn Photography

Lake Ontario
One of the best ways to celebrate the city in the summertime is to experience it from a boat. For the past two decades, a reliable option to do so is on a Mariposa Cruise. The best part about an evening spent on board is the stunning #views. The cruises offer some of the most iconic backdrops of the city, resulting in no shortage of the sunset-soaked skyline shots. Evening options include public dinner cruises and after-work Sip and Sail cruises. If that’s a little too “public” for you, you can also charter a yacht or powerboat.

Photo: Janet Vacanti

The Distillery District
No matter the type of evening you’re in the market for – from a quiet, romantic ice cream date to a big, tequila-filled night – you’ll find it at Toronto’s historic Distillery District. If a patio is your thing, the Distillery District houses one of the city’s best: El Catrin. The authentic Mexican cuisine caters to both traditionalists and outside-the-box foodies who enjoy a whole new take on tradition. The massive, colourful patio is complete with a vacation vibe (facilitated by the flowing tequila) and a fire pit. Tappo also makes a solid patio option – especially for the winos.

Now you know where to find us.