A Guide to Toronto's Secret Bars and Speakeasies in Dundas West

If you want a spot in the city to linger over drinks in soft warm lighting, while jazz music plays in the background, in a fashion that’s a true throwback to Prohibition, Cocktail Bar is the essential speakeasy. Only a short walk from Ossington Avenue, you can check out some of the other places on this list while stopping by here. The drinks at Cocktail Bar (often laced with house-made bitters) can’t be replicated or found anywhere else in Toronto. Owner Jen Agg brings her vision to timeless cocktails by blending really good alcohol with innovative ingredients that you won’t find on other menus. Less of a bar and more of an experience, this is one of those places where the money spent is worth it, if only because your temporary intoxication will allow you to magically drift back in time.

A short walk off Dundas Street W, down Ossington Avenue, is SP184. The entryway to this offbeat spot lies beneath a bright purple light in the alley behind the popular pizza joint, Superpoint. Through their dimly illuminated doorway, you’ll find a garage-like space where the regulars are throwing back shots of Jameson, spiced with fernet and Montenegro. Like most of the places on this list, there’s not much room, but that hardly matters, a DJ’s spinning tracks on the bar and you can order a side of pizza on Fridays and Saturdays.

Another intriguing hidden bar on Ossington Avenue is Gift Shop. In the backroom of a barber shop, there’s a one of a kind no-nonsense English bartender (with a really strong London accent), serving the most amazing concoctions. He’s known to the punters as H, has been in the business for decades, and takes his craft very seriously. Gift Shop is a small venue but it’s one of Toronto’s most unique drinking experiences, it won’t come as a surprise that this place gets super busy, so be prepared to wait if you haven’t made a reservation.

It’s easy to miss the only thing distinguishing this tiny and unassuming haunt – a wooden sign hanging in the window. The new owners haven’t replaced the old Nazare Snack Bar sign outside for years, but when you step into the Communist’s Daughter that kind of makes sense. Once a Portuguese diner, remnants of the bar’s past have been incorporated into its present-day. The nostalgic decor gives it a speakeasy feel, a nostalgic mixture of treasures dug up at a flea market, think early 20th century vibes with Russian-inspired paintings and posters. The romantic bohemian vibes are offset by the selection of beers served with things like pickled eggs. Young lovers, students, artists, and hipsters are drawn to this place for the live music on weekends. Over a decade ago, this was a true hidden gem and although the word has gotten over the years, the Communist’s Daughter has managed to retain its charm and soul.

Stowed away behind a pink bodega storefront, Mahjong is the latest addition to Toronto’s secret bars. You can enjoy a casual beer or glass of wine in the convenience-store style drinking space, or opt to go through a keyhole-shaped doorway into their colorful cocktail bar. Of course, mahjong tiles aren’t the only thing on offer here, the kitchen serves up Chinese small plates until midnight and the bright cocktails here are more like affirmations, they come with them too. For example, take the Tropic Thunder, a coconut soaked rum, lime, and pineapple beverage for when everyone on Instagram is on vacation and you’re stuck in Toronto.

From the outside, you’re looking for a basement dive bar marked with a heart that has been crossed. Unlovable has been a cult hangout in Little Portugal for quite some time, making its way on to almost every Toronto bar guide, and the venue is packed on the weekend. Nevertheless, it’s still a blink-and-you-miss-it-joint with a speakeasy tone, so it’s worth stopping by for the local brews and whiskey. The retro 70s decor, bathroom adorned with album covers, jukebox, and no-frills attitude are what makes it so lovable.

Disguised as a Tarot Card Reading joint, The Libertine is an underground speakeasy-style lounge, for which you need only follow the red light. The craft cocktails and cozy booths have a vintage feel to them, further adding to the Prohibition-era flavor here. While they don’t serve food, there’s an assortment of erratic snacks, Trix, Wasabi Pringles, Pop Tarts, and even Cookie Crisp.

This one is tricky to spot from the street but look for a dim hallway wedged between an exposed brick wall and a scotch-stocked bar. The Hole In The Wall is an incredibly narrow bar that sits inconspicuously on the corner of Dundas and Keele. Apart from comforting pub food, craft beer, and live music, they also serve brunch on the weekend. With limited space, they don’t take reservations, so make sure you grab a cozy table while you can.