In Winnipeg, there are a myriad of promotional agencies that trumpet the city’s great attractions: the market at The Forks, the gardens of Assiniboine Park, the historic sites in St. Boniface, and Fringe Festival events at Old Market Square. There’s also the local institutions like Bridge Drive-In, Rae & Jerry’s, and Kelecki’s that have become beloved little part of the city.

For anyone new to Winnipeg, these are all essential places to visit. (In the case of Keleckis, you’d better hurry — this longtime North End institution just announced that they will close for good next month). But for someone who really wants to dig deeper, and fully immerse themselves in this weird and wonderful little city we call home, here’s nine other ways to do so:

Cross the Arlington Bridge on foot

The Arlington Bridge is the best place to grasp the immenseness of the Canadian Pacific railyards it crosses, and the city’s former industrial and wholesale importance. A utilitarian structure (which, according to urban myth, was originally designed to cross the Nile in Egypt), few in 1914 could have imagined it would be standing a century later. But, it remains today, and from it can be seen the onion-dome skyline of the North End, and the distant office tower skyline of downtown.

Bonus marks: Cross the bridge again, this time while driving a town car listening to Ghostface Killah’s Apollo Kids album . You’ll feel more hood than you probably should.

Pick up beer at the Woodbine Hotel

The oldest bar in Western Canada, the Woodbine first opened in 1878, when Winnipeg was still a muddy village centred around steamboat landings and trails dotted with Red River Carts. Today, the Woodbine is one of the friendlier Main Street bars, and on weekend evenings there’s usually country bands performing. With no stage, the band crowds into the corner by the bar, playing for a packed house. Vendor orders are made at the bar, then picked up at a different counter in a separate room in the front of the building. It’s a strange system, which has everything to do with oppressively byzantine and antiquarian liquor regulations in this province. Yet, when it’s 1:30 am, and you’ve got a party to go to in the neighbourhood, it does the job.

Bonus marks: stay for a couple of drinks and some Patsy Cline on the jukebox.

Browse McNally Robinson Booksellers

By virtue of it being the main local book store in town — with neither the cluttered nuttiness of a typical used bookstore, nor many of the giftware trappings of a Chapters Indigo — this bookstore in a sleepy little shopping mall on Grant Avenue serves as the de facto literary centre of the city, and a place for aging River Heights matrons to parade around and go for lunch at the adjacent cafe. Sure, customers might talk about attending all the biggest book launches, loudly namedrop some local author whose sister they went to Kelvin with, or mention that the WSO just hasn’t been the same since Bramwell Tovey conducted. Don’t let that intimidate you, and know that they’re all walking out of there with nothing but the latest issue of Vanity Fair and Adrienne Clarkson’s autobiography.

Bonus marks: Go upstairs to the children’s section to watch 40 year-old dads try out the latest parenting fads on little Zadok and Isabella. Yikes.

Cycle the city’s tree-lined streets

The residential streets in many of Winnipeg’s old neighbourhoods– particularly Wolseley, old River Heights, and parts of Crescentwood — are some of the most beautiful and intact features of the city’s historical built environment. The trees that were planted along the street to add ornament to these neighbourhood have since grown taller that the century-old houses, and their branches reach across the street, forming a nave of a great cathedral. The best way to experience this is with a bike on a summer evening, when you can ride directly under the trees on either side of the road, and take it all in. Cross the footbridge that links Omand’s Creek Park with Sir. John Franklin Park, and it becomes possible to explore these neighbourhoods while avoiding the unsightly and obnoxious major traffic arteries.

Bonus Marks: Bring a flask.

Stop at Fox and Hounds Tavern at the St. James Hotel

Though it’s been 40 years since St. James and a dozen or so other cities, towns, and municipalities amalgamated to became the current City of Winnipeg, the distinction of “Sunny St. James” can still be felt at this Portage Avenue landmark. The Fox and Hounds isn’t a Winnipeg bar, it’s a St. James bar. While only a few kilometres from the relatively urbane nightspots of Osborne and the Exchange District, the Fox and Hounds is very much a small town Manitoba bar (with the added bonus of looking remarkably like the set ofCheers). Here, the girls sit at tables with their mothers, aunts, and cousins, and newcomers get a strange look when they walk through the door.

Bonus marks: Buy tickets for someone’s brother’s wedding social at the Silver Heights Community Centre next weekend.

Ride the 18 North Main

Not only does this bus route offer a chance to be “slightly insane on the 18 North Main,” like John K. Samson once sang, but it’s also the descendent of the North Main streetcar that the young Margaret Laurence immortalized in a poem from 1948. Here, especially during rush hour, the weary aspirations of north Winnipeg are still palpable; you literally feel them as they press up against you, and feel them filling your nose… Well, maybe that’s something else, but still. Riding the 18, you can see why so many North Enders became Marxists, and why even more went on to work their way out.

Bonus marks: Stop off at the old Salisbury House on Main and Matheson, right across from the transit garages.

Travel on the frozen rivers

The skating trails on the Red and Assiniboine at The Forks are an essential part of Winnipeg in wintertime. Beyond them, however, the rivers travel on and on. Cross-country ski to Assiniboine Park, snowshoe around Riverview, or just take a snowy shortcut to Osborne Village. The rivers in winter act as quiet avenues where the city can be seen in new ways, but also where Winnipeg’s timeless, natural features (including its cold winters) are best enjoyed.

Bonus marks: Stay until it gets dark (in winter, this is usually a few minutes after 3 pm). You likely won’t be able to see the stars, but you might see the Northern Lights.

Shop at the Regent Avenue Wal-Mart on the gloomiest, slushiest day possible

There are many big box stores in Winnipeg that act as emporia for cheap consumer goods and exhibits of human curiosities, but the Regent Avenue Wal-Mart is one of the biggest. Want to rub shoulders with thousands of people wearing Looney Tunes pajama pants? You’re in luck. This depressing excursion is best experienced on a cloudy, slushy day in late February, when the darkness of winter has gone on about as long as it can. Like any big box store that just doesn’t care any more, the front entrance becomes something of a lake of mud and melted snow. Just to warn you, Winnipeggers operate a shopping cart about as well as they drive.

Bonus marks: Try to find the strange beauty in this. Try and tell me Western Civilization is not disintegrating. Try to find the meaning for all of us living here. Please.

Stop at Stella’s on Sherbrook on the first nice Sunday of the spring

It’s fitting that this typically occurs around Easter, because this is the day that Winnipeg rises from the dead. The charms of winter have long since gone, after weeks of gloom and cold (we call this February), when suddenly, the sun comes out, and not just in a “this would be a nice day to go skating” kind of way. It feels like Spring, and everyone can sense it. Sure, snow might still be on the ground in dirty piles, but temperature is nice enough to feel warm in the sun again. There are many places to enjoy this feeling in Winnipeg, but the Stella’s on Sherbrook Street is one of the best: it gets direct sunlight, and is busy with people who feel the same euphoria you do. There will definitely be a line out the door to get a table, but on this day, you’ll love that there is.

Bonus marks: spend the rest of the day outside not wearing a jacket. You’ll probably catch a cold that lasts a week, but who cares? Summer’s coming soon.

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Robert Galston likes to write about Winnipeg, urbanism, and other very, very exciting topics. Follow him on Twitter @riseandsprawl



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