Cherry's High DIVE/GOODNIGHT Cocktail Club

What is Cherry's High DIVE/GOODNIGHT Cocktail Club? Occupying two distinct levels at 488 Wellington Street West directly across from The Well, this dual-concept venue pairs a sun-drenched, retro-fueled dive bar upstairs with a moody subterranean speakeasy below. Street level at Cherry's High Dive delivers a high-energy 1970s rec-room aesthetic with vintage barstools, a bustling patio, a leopard-print pool table, and an analog photo booth. Down an unassuming side stairwell, Goodnight Cocktail Club shifts the mood entirely into a sultry, dimly lit hideaway wrapped in rich wood panelling, stone walls, and plush velvet booths.

Cherry's High DIVE/GOODNIGHT Cocktail Club Menu & What to Order Upstairs, the kitchen focuses on tavern-style bar pies cut into shareable party squares, with the Spicy Soppressata drizzled with hot honey and the Truffle Mushroom standing out as immediate crowd favorites. Pair your slices with pull-apart mozzarella sticks, crispy calamari, or a cold draft lager served in frosted glassware. Downstairs at Goodnight, the drinks take center stage with precision concoctions like the Flamingo Room crowned with yuzu foam, spirit-forward classic martinis, and velvety espresso martinis paired with elevated bar bites like beef tartare and stuffed dates.

Know Before You Go Both venues accept reservations via Resy, though Cherry's saves walk-in space around the main bar, pool room, and outdoor patio. The room becomes strictly 19+ after 5:00 p.m., drawing intense post-work and late-night crowds on weekends. Street parking along Wellington is scarce, so taking the 504 King streetcar or 510 Spadina line is the most hassle-free route.