Is South Osborne the hippest neighborhood in Winnipeg? You Decide!
You know you’re in South Osborne when you’ve got more artisanal coffee shops per capita than anywhere else in the city… and maybe even more hipsters (young, trendy individuals who are into alternative music, fashion, and culture) per square foot too!
I once saw a guy riding a unicycle while juggling avocados here—now that’s what I call peak South Osborne culture!
Why? It perfectly encapsulates the offbeat charm of this neighborhood. It’s like highlighting the unique experiences you might encounter in this community, where the unexpected is part of everyday life.
But if you’re not convinced yet that this part of town is the cat’s pajamas, stick around. I’m about to take you on a journey through the quirkiest, coolest, and downright funkiest spots on this side of the Red River.
So grab your toque, lace up those vintage kicks, and let’s dive into what makes South Osborne the hippest neighborhood in all of Winnipeg.
Best Time to Visit South Osborne in Winnipeg
The best time to visit South Osborne, Winnipeg depends on what you want to experience. For warm-weather strolling and patio dining, aim for June to August.
But if you enjoy budget-friendly deals and homey vibes, September to May offer a quieter scene.
Things to Do at South Osborne in Winnipeg
1. Shopping
South Osborne is known for its funky shops. You can spend hours just wandering around, popping into vintage clothing joints, flipping through books at McNally Robinson, or checking out art galleries.
And if you’re into supporting homegrown talent (which you totally should be), places like Out of the Blue and McNally Robinson Booksellers have all kinds of goodies from local brands and artists, so you can take a piece of Winnipeg home with you.
Trust me, you won’t want to leave empty-handed!
2. Dining and Drinking
This neighborhood has a solid lineup of over 15 restaurants, so whatever you’re craving, chances are you’ll find it.
And if you’re in the mood for a chill hangout, you can also swing by one of the cozy cafes or bistros for a laid-back vibe and some tasty eats.
But if you want to splash out a bit or celebrate something special, they’ve got a handful of fine-dining joints that’ll really impress you.
3. Enjoying Entertainment
You can’t miss the Park Theater if you’re visiting South Osborne! This historic venue hosts live music gigs, hilarious comedy shows, and even movie screenings, making a night out feel extra special.
And if you’re looking for more active entertainment, there’s a bowling alley nearby, perfect for a bit of friendly competition with your buddies.
And right next door? An arcade!
It’s like stepping into a retro wonderland with all those games flashing and beeping.
4. Relaxing
Another thing you can do in this neighborhood is take a stroll or bike ride along the Assiniboine River. It’s super serene, especially when the weather’s nice!
Plus, there are some sweet parks along the way where you can simply relax and appreciate the atmosphere.
But if the weather’s not cooperating or you’re just looking for some indoor relaxation, there are a couple of cool museums and art galleries around to check out.
Though they’re not huge like the ones downtown, they’ve got their own charm and often feature some pretty neat local artists.
Where to Eat Near South Osborne in Winnipeg
1. Oakwood Cafe
I love the atmosphere at Oakwood Cafe—super relaxing and welcoming; it feels like I’m dining at my best friend’s place!
Their Cowboy Breakfast Bowl is something I always come back here for. A mix of hand-cut potatoes, scrambled eggs, crispy bacon, sausage, onions, creamy avocado, and gooey Cheddar cheese, all topped off with a kick of hot sauce.
And get this, you can customize it however you like—you can go veggie by substituting tomato and extra avocado or kosher-friendly with brisket and mushrooms instead of the pork and cheese.
The restaurant also offers different kinds of pancakes, but their Peach Bacon Pancakes are the winner here! They’re fluffy buttermilk pancakes stuffed with bacon and juicy peaches served with a dollop of cinnamon honey butter on the side.
It’s like breakfast and dessert rolled into one delightful stack.
2. Sous Sol
Sous Sol is all about Canadian cuisine, but with a modern twist. Their menu’s always changing with the seasons, which keeps things exciting.
Now, if you’re wondering what to order, their Tartare MB Beef is a crowd favorite—tenderloin with all these delicious fixings like egg yolk, Worcestershire, bread, and a bunch of flavorful add-ons like capers and shallots.
And if you’re feeling adventurous, go for the Roast Bone Marrow. They serve it up with smoked honey, confit garlic, and herbs, along with some crunchy breadcrumbs and French bread to scoop it all up.
Where to Stay Near South Osborne in Winnipeg
1. Fairmont Winnipeg
Fairmont Winnipeg is like the crown jewel of downtown stays. Here, you’ll wake up to either a killer view of the historic Exchange District or the beautiful confluence of the Red and Assiniboine Rivers.
The rooms and suites are top-notch, like something out of a dream. Plus, they’ve got some fancy dining options that’ll make your taste buds sing.
And when you’re not out exploring, you can hit up their fitness center or take a dip in the indoor saltwater pool.
2. Inn at the Forks
Another great option to crash near South Osborne is the Inn at the Forks. This hotel is the epitome of modern chic, located right at the Forks National Historic Site.
As per the rooms, they’re so airy and stylish, with all those sleek finishes that make you feel all kinds of fancy.
And the location—it’s the ultimate home base for exploring Winnipeg. You’ve got the waterfront right at your doorstep, plus all those museums and historical spots nearby.
But it doesn’t stop there! In case you need some serious rest and relaxation after a day of adventure, they also provide a full-service spa.
And when hunger strikes, you won’t be disappointed. Their restaurant serves up delicious contemporary cuisine.
3. Humphry Inn & Suites, Downtown Winnipeg
— Media credit: coach_satira
Humphry Inn & Suites is a pretty decent hotel, especially if you’re watching your wallet. You’ll get your standard room with a nice complimentary breakfast buffet thrown in and parking (which is always a bonus!).
Plus, there’s an indoor pool if you feel like taking a dip and a 24-hour coffee bar for those caffeine cravings.
It might not be the fanciest joint in town, but it’s comfy, convenient, and affordable—perfect for those who prioritize exploring the city over in-room amenities.
Tips When You Visit South Osborne in Winnipeg
1. Plan your parking spot ahead.
Parking can be tricky on Osborne, especially on weekends and during peak hours. If you’re driving, be prepared to circle a block or two or park on a side street.
There are also a few paid parking lots in the area.
2. Wear comfy shoes.
South Osborne is a very walkable area, so you’ll likely be doing a fair bit of strolling. Wear comfortable shoes that can handle pavement and cobblestones.
3. Bring cash.
While many stores accept credit cards, there are still a few smaller shops and kiosks that are cash-only. It’s always a good idea to have a bit of cash on hand just in case.
4. Be patient.
South Osborne is a popular neighborhood, so expect things to be a bit crowded, especially on weekends. Be patient when waiting for a table at a restaurant or browsing in a store.
5. Take your time.
South Osborne is a great place to wander around and explore. Don’t try to pack too much into your visit.
Just relax and enjoy the vibe of the neighborhood.