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Osborne St. South

Like it’s neighbour to the north, South Osborne is a groovy section of the city where cool kids congregate while, due to the abundance of families in its Riverview and Lord Roberts neighbourhoods, it also has a very cozy, friendly neighbourhood sort of feel. 

The south part of Osborne Street cuts a line between these two neighbourhoods, which are some of the oldest residential areas of Winnipeg. Sandwiched between these abodes is a street chock full of fantastic casual eateries, along with The Park Theatre, arguably Winnipeg’s busiest venues for live music film and artsy happenings. Plus, South Osborne is where you can access the verdant, riverside parklands of Kingston Row where, come winter, you can make your way down to the end of the Red River Mutual Trail for some serious skating and winter fun. 

Where to eat

It makes sense to start with Deseo Bistro, as it certainly is the most nationally acclaimed eatery on South Osborne, having been featured on the several top 50 restaurant in Canada lists. Chef Scott Bagshaw’s menu, who now regularly helms his second restaurant Enoteca in River Heights, is jammed packed with huge flavours representing everything from Spanish tapas, to classic French, to South American meat-centricity. This place has one of the best drink programs in the city, great staff, and some rocking dishes that regulars would riot if they ever took off the menu, including the crunch salad, chorizo and figs, and a mac & cheese made with hand-rolled pasta in a manchego/Spanish paprika béchamel with chorizo crumble that will seriously have you licking the plate. 

BMC Market has quietly become not just a neighbourhood favourite, but a destination spot for arguably the most authentic Mexican tacos in the city. Owners Betty Calderon-Villasenor and husband Rigoberto are from Morelia, Mexico, and her tacos are just as her grandma used to make back in Central Mexico (no cheese ever, just cilantro and house-made salsas. She hand forms the tortillas in front of your eyes to order, while all the meats are slowly braised. The room is small and cute, they serve Mexican beers, and the best part of all is you get three tacos for either $5 or $6. It’s a total gem.

Another gem revered by the neighbours is the Oakwood Cafe, where everything is made from scratch and the place is almost always packed, be it breakfast, lunch or dinner. Owners Peter Paley and Alix Loiselle are about as affable as it gets, and they even take the time to respond to nearly each and every online review, so you know they take the utmost care and pride in their done right diner-style fare.

New to the neighbourhood, and now hugely popular, is Vera Pizzeria.  The stunning Neapolitan pizzas and outrageously good meatballs that get served in this tiny restaurant (which has a cute, even smaller patio) more often than not mean waiting for a table is mandatory – as they don’t take reservations. But don’t worry, it’s worth the wait, plus you can skip the line if you want to order takeout. The young staff is super friendly, making Vera a seamless fit in South Osborne. 

Another Italian joint of note is Monticchio Ristorante where pasta is king, especially the Pasta Sambuca which features linguine topped with sautéed scallops, mussels and prawns, roasted red peppers and garlic, all finished with a splash of Sambuca and cream.

One of Winnipeg’s most renowned locales where legendary desserts like the "goog special" (a blueberry milkshake topped with banana ice cream and hot fudge) have made the Bridge Drive-In an institution for more than 50 years. This walk-up summertime ice cream spot is just a short stroll from the pedestrian Elm Park Bridge and sees vast line-ups throughout the summer.

The newest eatery in the hood is Blind Tiger a fancy coffee shop by day then a speakeasy come evening with a menu full of French fare. 

Where to shop

Thousands of books, comics, science fiction and fantasy reads, and interesting antiques and collectibles adorn the shelves of Nerman’s Books & Antiques while more than 100,000 used books line the shelves of Burton Lysecki Books – the place to go for books on Manitoba history, Western Canada, First Nations, fur trade history and the Canadian military. 

At Grape & Grain you can say hi to your friendly neighbourhood beer guy. They sell wine and beer-making supply needs with over 1,000 items available for purchase. Sweet seekers stop in at Chocolate Zen Bakery to get their chocolate fix. Rich, moist brownies, towering tortes, cream horns, cookies, pastries and more fill the gleaming dessert showcase.

Bijou brings the bling to the neighbourhood with its beautiful collection of engagement and wedding rings and stylish handcrafted jewellery. 

Whether searching for a poker set, role-playing game or special edition of Monopoly, Game Knight stocks today’s hottest board and collectible card games, alongside classics, like cribbage and darts. 726 Osborne Street, 204-487-4263.

Things to see and do

Churchill Drive Park runs along the banks of the Red River, making it one of the city’s longest continuous riverfront parks near downtown. Its long, narrow shape makes it a great spot for trails, which are used by joggers, cyclists, dog walkers and cross-country skiers, depending on the season. Located along Churchill Drive, east of Osborne Street.

For an intimate concert experience, head to Park Theatre and Café where live music is scheduled almost every night of the week (they have over 300 shows per year). While here, enjoy a gourmet cup of java or a fine selection beers. 

Finally, avoid gutter balls at Park Alleys where special events are a constant, including ladies night, Friday fun nights, and glow bowling.

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