Penny's

What is Penny's? Anchoring the corner where Junction-Wallace Emerson meets Bloordale, Penny's at 1306 Bloor Street West is a cherished, community-driven dive bar and indie music venue helmed by longtime hospitality veteran Olivia Jewer. Behind a modest storefront marked by glowing retro signage, the low-lit space unfolds with sharpie-drawn wall murals, a long wooden bar counter, and a back stage wired for amps and drum kits. Seating centers around worn pub tables and bar stools that fill quickly with neighbourhood locals, touring indie musicians, and open-mic regulars.

Penny's Menu & What to Order Penny's keeps things refreshingly simple at the bar, eschewing pretentious cocktail mixology in favor of well-poured rail drinks, shot-and-beer specials, and a rotating draft lineup of Ontario craft beer stalwarts like Left Field and Woodhouse. While drink orders rule the night, bar snacks lean casual with quick bites like crispy vegetable samosas and chips, alongside a welcoming BYO-food policy that lets patrons bring in slices from neighboring Bloor West pizza joints. Order a cold pint of local IPA or a crisp lager paired with a whiskey shot, settle into a booth, and take in the live room sound.

Know Before You Go Penny's is strictly walk-in only, operating daily from late afternoon until last call at 2:00 a.m. Tuesday open mics, Wednesday and Thursday karaoke, and weekend live punk and indie sets bring wall-to-wall crowds by 9:30 p.m., so arriving early is crucial to snag a table. The bar sits just a five-minute walk west of Lansdowne subway station, and note that the washrooms require a trip down a steep flight of basement stairs.