The Most Fun You Can Have in Toronto on a School Night

With all the regular gatherings and parties happening weekly in Toronto between Monday and Thursday nights, your weeknights here don’t have to be weak nights

Sure, Friday and Saturday are infamous as the sexiest nights to party. But they also come with large crowds, long lines and overpriced hype. Mondays through Thursdays may be the underdogs of the social calendar, but they’re free of the high stakes of the weekend. Everything tends to be a little more relaxed, spontaneous and experimental. There’s an undeniably giddy feeling that all of us school night rebels actually want to be out. And if you’re a weeknight warrior, you probably won’t have to shout to be heard or even pay full price. Whether you’re taking a break in the work week or getting revved up for the weekend, here are a few of the most inspiring and original weeknights out in Toronto.


Foodie fun and cocktails

The Drake Hotel’s 86’d Mondays is a free weekly event featuring food and cocktail competitions and tastings. Local chefs, suppliers and bartenders face-off in themed “smackdowns” for such bragging rights as the best breakfast sandwich, ceviche, fried chicken, guacamole, oysters, or gin cocktail in town. You’ll have the opportunity to snack or sip on them all and vote for your favourite. After the winners are crowned, the bar breaks out into a dance floor with live music from high energy bands like the St. Royals and the Lonely Hearts.

If you prefer home cooking, the Depanneur hosts cooking workshops in its warm and homey kitchen every Monday night. You can fraternize with the locals while learning how to make everything from Polish pierogies to French sauces, handmade chocolates, and citrus marmalades. You can also share the communal table at a Friday night “open mic” drop-in dinner where professional and amateur chefs alike have been known to prepare masala dosas, Yucatan tapas, Indian street food, and three-course Burmese feasts.

Have strangers rate your music

Brush off your best vinyl and bring it on over to endearing neighbourhood watering hole, the Communist’s Daughter. At its weekly DeCIDE on the B-SIDE, you’ll sling back a microbrew and listen to the A-side. And then, in true communist fashion, come to a consensus on whether the B-side is worth the commitment or hightail it to the next mystery record. Pro and con barflys take the floor to defend their stance.

Like a TED talk, but weird

Running for more than 15 years at The Garrison, the widely popular Trampoline Hall is a monthly lecture series like no other. Hosted by the always entertaining improv maven Misha Glouberman, the show features three talks on any subject from the mundane to the arcane, followed by a lively Q&A. The only caveat is that a topic cannot be the speaker’s area of professional expertise (though they can certainly be knowledgeable). Recent topics have included “On Having a Penis,” “Anxiety,” and “I was a Public Speaking Champion.” Every event is lovingly prepared by special guest curators and set designers.

The regularly sold-out performance has travelled to New York, Vancouver and Montreal, and even did a 10-city U.S. tour. It’s a daring mix between improv and TED talk, or as The New Yorker described it, “a lecture series celebrating eccentricity and do-it-yourself inventiveness.” A tip: Tickets sell out quickly but you can score them at Soundscapes, starting the Thursday before the show. Or try your luck with the limited same day tickets at the door.


Upping the ante on buck-a-shuck

It’s hard to beat trendy Ossington strip’s chic and modern Boehmer on a Tuesday night.  You can indulge in buck-a-shuck oysters, half-price bottles of wine, and $22 lobsters. Enjoy a crisp glass of Alsatian white over a perfect plate of juicy PEI oysters and buttery steamed lobster, all the while saving your loonies for the weekend.

You can also surf weeknight buck-a-shuck specials at other top-notch establishments like Pearl Driver (100 oyster for 100 bucks on Thursdays), Barhop (Tuesdays), Bestellen (Wednesdays), Hopgoods Foodliner (Monday), Hole in the Wall (Tuesdays), The Yukon (Mondays).

Beer and blocks

The Gladstone hotel wants to take us all back to our carefree kindergarten days. Everything is awesome with their recently launched Lego and lagers extravaganza on Tuesdays. The Melody Bar provides the boxes of lego, so you can finally build your dream home. And if your inner child still can’t get enough, there’s Music Bingo on Wednesdays and Adult Colouring followed by live music on Thursdays. Sip a signature cocktail, while trying to stay in the lines.

Dance like nobody’s watching

Perfect your dance moves at the Dovercourt House. There’s drop-in classes every night of the week, from salsa to tango, hula hooping and swing. Every first Tuesday of the month, try a free West Coast Swing dance lesson and stay afterwards for the social.

At the Piston’s Tuesday Indie Nights, you’re likely to discover original singles and catchy covers by local guest bands. Or head for a sure thing at the Drake Underground, the hipster hotspot known for weeknight indie shows and DJ dance parties.

Jazz things up

Every night is legendary at jazz institutions like the Reservoir Lounge. But on “Tipsy Tuesdays,” the cover is only $5 to hear the full-bodied jazz and swing rhythms of Juno winner Tyler Yarema and his seven piece band. If the swanky Shangri-La is more your style, you can warm-up by the lobby lounge fireplace, listening to free weeknight musical stylings like the smooth blues of Errol Fisher (Wednesday nights). Or discover where the musicians themselves go to fill-up on live music. The 40-year-old jazz and blues bar, lovingly known as The Rex, is open every night and plays more than 19 shows per week.


Join a flash pop ensemble

If you’re looking for some truly original and local entertainment, Choir! Choir! Choir! has gained cult status as a flash ensembling of pop singer wannabes. A group of familiar and unfamiliar faces converge for drop-in impromptu singing sessions Tuesdays and Wednesdays at the back of Clinton’s Tavern. Whether you have real singing chops or just like to belt it out in the shower, the sessions are open to everybody.


Pick-up a lyric sheet, channel your best baritone, alto, or soprano, and spend the eve mastering three-part harmonies of your favourite pop songs. You’re guaranteed to be in good company and meet some characters; the impromptu group has performed at the Art Gallery of Ontario, the Juno Awards, TEDx Toronto, and the closing gala of the Toronto International Film Festival.

Yuk it up

Now in its 20th year, Comedy Night at Spirits Bar and Grill has become a fixture in the Toronto comedy scene. Hosted by Yuk Yuks comedian Cal Post, it’s a fun, frolicking and free open mic with an impressively long and diverse roster of professionals and amateurs. The unassuming stage has even been graced with impromptu performances by the likes of Robin Williams, Lewis Black, and Seth Meyers.

If you’re Uptown, the Pro/Am show at Absolute Comedy is also sure to deliver lively professional headliners and emerging talent with an equally rowdy crowd.

Open house for art lovers

The last Wednesdays of every month, the 401 Richmond Galleries host an after hours open house of their six galleries and the rare musical instrument collection of the Musideum. Toronto curator William Huffman is also on-hand to lead free tours of the current exhibitions. March’s open house features an annual Easter Art Hunt where original hand-painted eggs by gallery artists are hidden throughout the 200,000-square-foot heritage building.


Variety is the spice of life

Since 2006, Laugh Sabbath has built a critically acclaimed collective of original comedic voices, many of whom have gone on to star in their own TV shows, films and stand-up tours. Hosted by the Comedy Bar, the weekly themed variety shows bring out some of the best comics in the city. Expect the unexpected in the form of stand-up, sketch and character comedy accompanied by music. And maybe even a comedy competition parody judged by trolls.

AGO First Thursdays

The first Thursday of every month, the Art Gallery of Ontario throws a party after regular gallery hours. With a cocktail in hand, you can roam one of the finest art collections in the country while taking in the sights and sounds of loud bands, experimental DJs, and interactive performance art. In addition to emerging local artists and big names like Patti Smith, Grandmaster Flash and Ai Weiwei, there’s always entertaining people-watching.

The Thirsty Games

Play a couple of rounds yourself or just watch the “fierce” weekly competition for King of the Court at Spin, the 12,000-sqare-foot ping pong social club owned by Susan Sarandon. You can also try your hand (the one that’s not holding a pint) at bocce ball or shuffleboard at Track & Field, Toronto’s first bar to merge cocktails and craft beers with lawn games.

If board games are more your speed, the trendy and impeccably designed Addison’s Residence does their version of “Afternoon Tea” with $4 drinks from 5 until 10 pm every Thursday. You can play Monopoly or foosball in the rec room until the DJ gets the party started. Meanwhile at Night Owl, the two storey bar and games arcade, Thursday means all you can eat tacos, boozy root beer floats, and live hip hop and R&B covers.

PRO TIP: Above all else, going out on a weeknight means revelling in a city that’s yours for the taking, being spontaneous and savouring those places that are usually overrun on the weekends. It’s a carte blanche to go see the sharks after dark at Ripley’s Aquarium, sip cava cocktails at the tiny, always bustling Bar Raval, find a new neighborhood local like The Walton, or skip the reservation at Dandylion and just show up.

The Most Fun You Can Have in Toronto on a School Night
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