Winnipeg is bubbling with both classy drinking establishments and proud dive bars alike, with fun, reputable spots on just about every major street. For this culinary trail we are going to move from the heights of sophistication, through to watering holes where you can meet the artistic locals where the music just may get loud, but the drinks will always be top notch.
The Palm Lounge
222 Broadway, located in The Fort Garry Hotel
The Fort Garry Hotel, Spa and Conference Centre.
Inside the Palm Lounge.
With its domed ceiling, lavish draperies and gilded walls, the Fort Garry Hotel’s Palm Lounge provides step back in time. The 101-year-old railway hotel is a grand dame of historic architecture in Winnipeg with this lounge being its social epicentre. The servers and bartenders are in dapper dress, the clientele is to refrain from wearing hats, there is frequently someone tickling the ivories on the grand piano or some live jazz trio, the cocktails are all of the classic variety and the wine and beer menu is well thought out. What more could one ask for to start the evening off with an air of dignity?
Neighbourhood: Exchange District
185 Lombard Avenue
Over in the Exchange you’ll find several spots of note, a great starting point of which is Bailey’s. One step inside and you’re instantly transported to an Olde World English drinking room where a massive oak bar serves as the hub for a multi-room lounge. Portraits of long-gone British aristocrats decorate the brick walls and yet nostalgia doesn’t completely dominate here as many screens are simultaneously tuned into the sporting events. The main booze draw comes byway of an extensive scotch list – which Bailey’s insists is the biggest in the city – along with a good smattering of cognacs and wine.
Albert Street Cocktail Company
Neighbourhood: Exchange District
91 Albert Street
The Autumn Sweater.
Inside the Albert Street Cocktail Company.
A couple blocks over is the Albert Street Cocktail Company, Winnipeg’s newest and most drink-focused room. It’s a dandy of a place, with industrial style wood tables that can be cranked to various heights, stately furniture, and an extensive cocktail menu that shows what glassware your drink will come in. This are “handcrafted” cocktails, so it takes some time for the bartenders to shakeup and strain these numbers, but it all ends up being worth it (even at around $12 per drink).
Prairie 360 Whiskey Lounge
83 Garry Street
Whiskey selection at Prairie 360.
New York Sour.
At 28 floors up in the middle of downtown, nothing beats the view inside Prairie 360’s Whiskey Lounge. This masculine room – complete with deep comfy chairs and a slightly disturbing artwork featuring Winnie the Pooh in a hunting scenario – is a great counterpoint to its sister room, the piano lounge across the hall. Lounge guests come for the view, sure, but it’s the tipple list that keeps this downtown spot on the must-do list. The 30th floor revolving restaurant and its lounges stock an estimated 240 spirits and 200 bottles of wine. The whiskey and scotch menu is well thought out with options divided into five tasting categories: floral and fragrant; smoky and peaty; malty and dry; rich and round; and fruity and spicy.
75 Forks Market Road
Crafting cocktails at Smith.
Down at The Forks, inside the Inn at the Forks, is where you’ll find Smith, whose rustic-chic lounge features “antler” chandeliers, Hudson Bay blanket banquettes and rough-hewn tables. Smith’s house-made bitters and syrups are good examples of the growing trend of mixology in Winnipeg, with most of them being put to good use on a cocktail that is a double-shot of classic and modern cocktails.
RAE and Jerry’s Steakhouse
Neighbourhood: West End
1405 Portage Avenue
The lounge inside Rae and Jerry’s.
Squint tightly and you might just see Mad Men’s Don Draper tackling a Rusty Nail in a dark corner. That’s the kind of throwback vibe Rae and Jerry’s, one of Winnipeg’s most treasured steakhouses‚ exudes from every pore. This place is so old it’s new, with red vinyl banquettes, swivel chairs and dark panelling and draperies that scream retro sophistication. The lounge attracts a mishmash of devoted clientele – from stylish seniors, dealmakers, professionals, hipsters and the creative class.
The Toad in the Hole Pub and Eatery / The Cavern
Neighbourhood: Osborne Village
108 Osborne Street
The Toad in the Hole.
When it comes to Obsorne Village, one of Winnipeg’s liveliest nighttime neighbourhoods, The Toad in the Hole Pub and Eatery just may be the pick of the pool. It features a whisky bar – which is exclusive to a crowd 25 years old and up – that features over 160 whiskies from around the globe, a main pub area that is always hopping with locals, while downstairs The Cavern frequently hosts great bands in an intimate (and a touch loud) environment.
Good Will Social Club
Neighbourhood: West End
625 Portage Avenue
On tap beer at Good Will Social Club.
Sangria at Good Will Social Club.
The hipster capital of Winnipeg could very well be the Good Will Social Club, which just celebrated its first full year in business. A long communal table is the main feature of one room, along with a pizza by the slice counter from A Little Pizza Heaven and a VHS player and TV (replete with a solid selection of VHS films). The other side is wide-open with a stage at the back (where some form of live music happens every night) along with a dance floor and bar that does solid cocktails and has great beers on tap.
The Handsome Daughter
Neighbourhood: West Broadway
61 Sherbrook Street
Gin and soda at The Handsome Daughter.
Ambiance at The Handsome Daughter.
If you were to dare embark on this cocktail laden tour, then you best finish things up at Winnipeg’s proudest new dive bar, The Handsome Daughter. It’s a sweet little room on Sherbrook Street that stays open until late, like really late, seven nights a week. They have fun cocktails like corpse rivers and rum sours, and they also do fun snacky food. Plus, it’s a great place to meet all the cool kids who will be right there with you sipping away and listening to quality tunes during the wee hours of the morning.