Morten Andersen tends to distrust any pub that has been open long enough to call itself an institution, on the grounds that most of them coast. Hemingway's, after 42 years on Cumberland Street, has earned the word honestly. It still opens every day of the year and it still fills four patios.
The address is 142 Cumberland Street, in the heart of Yorkville, a short walk from the Bay subway station. Hemingway's has held this corner since 1980 and it now spreads across three floors with four separate patios, including the all-season rooftop it is best known for (Bloor-Yorkville BIA). The rooftop runs misters in summer and heaters in winter, which is the detail that separates a marketing patio from one people actually use in February.
The sporting credentials are real rather than decorative. The bar carries 20 screens and tunes them to international sport as readily as the local franchises, which in a Toronto room usually means the Raptors, Leafs and Blue Jays sharing wall space with rugby and football from the other side of the Atlantic (Hemingway's official site). That international leaning is the reason a homesick rugby follower can find a Six Nations match here without negotiating for the sound.
The kitchen is the genuine oddity, and the better for it. Hemingway's runs a New Zealand-inspired menu, a nod to the founder's roots, so the lamb shank with mint jelly sits alongside the expected nachos and pub plates. Order the lamb shank if you want the thing the room is named for, the nachos if you are settling in for a full afternoon of sport, and a pint upstairs once the rooftop is open. The food will not rewrite your week, but it is honest cooking that suits the patios.
Who it is for is the Yorkville regular, the after-work crowd off Bloor Street, and the visitor who wants a drink with a view rather than a basement. It works for a relaxed match on the screens and it works for a summer evening on the roof, which is a wider range than most sports rooms manage. For Toronto's arena-scale venues, our roundup of the best sports bars in Toronto covers the bigger barns.
Best time to go is a warm evening when the rooftop is open and a match is on the screens below, which lets you move between the two as the game demands. Weekly themed trivia nights, including a long-running Office quiz, pull a younger midweek crowd if that is your register. Avoid a peak Saturday in summer without a plan, because the rooftop fills fast and Yorkville foot traffic does the rest.
The room rewards a slower visit. Hemingway's is not trying to be a slick sports barn, and the warren of floors and patios means you can find a quiet corner for a conversation or a loud one for a match without leaving the building. Forty-two years of trade have given the staff the unhurried competence that newer bars spend a decade chasing, and the place treats a quiet Tuesday with the same care as a packed long weekend. For a homesick visitor or a Yorkville local, that steadiness is the point.
Hemingway's earns its place in this guide as Yorkville's most durable bar, a multi-level institution that pairs international sport with the only rooftop in the neighbourhood worth planning an evening around. For a drink above the street with a game in earshot, it is the Yorkville pick. For a wider tour of the city, start with our Toronto bar guide.
Sources: Hemingway's official site; Bloor-Yorkville BIA listing; The Rooftop Guide, Toronto.
