The Best Bars in Yorkville, Compared: Rooftops, Hotel Lounges and Cumberland Street Classics

Yorkville is usually pitched as a shopping district, but after the boutiques close it turns into one of the most varied drinking neighbourhoods in Toronto. Within a few blocks you can sip a martini surrounded by contemporary art, drink on a rooftop with a view of Bloor Street, or settle into a pub that has been pouring pints for decades. Here is how the main options compare, based on the Bloor-Yorkville BIA's bar-hop guide and a roundup of the city's hotel bars.

Hotel Bars: Polished and Late

If you want a quiet, upscale nightcap, start with the hotels. The d|bar at the Four Seasons (60 Yorkville Avenue) is a lounge with velvet couches and plush seating, with a craft cocktail list built around seasonal ingredients and cheese and charcuterie boards on the side. Sunday nights from 9pm a live DJ takes over. Design Lines magazine singled it out as a spacious but intimate spot with plenty of tables for two, and named the espresso martini as its signature drink.

The Writers Room Bar at the Park Hyatt (4 Avenue Road) sits on the 17th floor and leans on skyline views and rooftop access. The focus is on reimagined classic cocktails paired with shared plates and desserts. It suits an occasion drink more than a casual pint.

Rooftops and Patios: Best for Warm Evenings

Skylight at the W Hotel (90 Bloor Street East, 9th floor) mixes indoor and outdoor space under bohemian decor, with sunset views over Bloor Street, shared plates and craft cocktails. The Pilot (22 Cumberland Street) is a long-running institution with a multi-level layout; its rooftop Flight Deck holds 185 and runs from March to December, while the main floor hosts live jazz on Saturday afternoons from 2:30pm to 5:30pm.

On Cumberland Street, Hemingway's (142 Cumberland Street) has three bars, a restaurant and four patios that are heated and covered in winter, plus 24 draught beers and weekly events such as trivia and a silent disco. The Oxley Public House (121 Yorkville Avenue) is a British-style townhouse bar with a broad beer and wine list and two patios.

Cocktails and Wine: The Slower Pour

Sofia (99 Yorkville Avenue) is known for a curated cocktail menu with signature martinis and mocktails, in a room that rotates artwork from the neighbouring Tagliatella Galleries. Alobar (162 Cumberland Street) offers a lounge, dining room, bar and a terrace surrounded by greenery, with curated wines and cocktails and cuisine from chef Patrick Kriss; it is open until midnight Thursday to Saturday and was included in the 2024 Michelin Guide. Bar Reyna (158 Cumberland Street) is a Mediterranean-inspired Victorian townhouse with a refreshed patio and a menu of shareable plates.

The Budget-Friendly Pick

Earls Yorkville (55 Bloor Street West, in the Manulife Centre) is the casual option, with a kitchen and bar open until 1am Sunday to Thursday and an afternoon happy hour from 2pm to 5pm daily that the BIA describes as running from $4 tacos to $10 cocktails.

How to Choose

For a date or a celebratory drink, pick d|bar, the Writers Room Bar or Alobar. For a big group or a sunny evening, head for The Pilot's Flight Deck, Hemingway's or Skylight. If you want to spend less, Earls' happy hour is the clear value play, and for a relaxed pub night the Oxley is an easy default. Hours, menus and seasonal terraces change, so check each venue before you go and plan a safe ride home.