I decided to begin our neighbourhood guide to Winnipeg with Osborne Village for two reasons. First, it's the neighbourhood I call home. And second, it's a pretty firmly established destination in Winnipeg. Although Osborne Village is full of great spots, I've narrowed it down to a special group. And while all of these places definitely come with my recommendation, I've organized each category from highest recommended to lowest. (Think of it like "You absolutely cannot miss this!" down to "This is still pretty great.") Please enjoy and feel free to comment below!
A beautifully intimate atmosphere, flat out fantastic food, and delightful, unusual cocktails. This place led the trend of little plates in Winnipeg and continues to do so very, very well. They don't take reservations, but, if you arrive well before you plan to eat (we're talking easily an hour plus if you have a table of four or more on a weekend), you can leave your name and number and they'll call you when your table is ready. That way, you can do some shopping or have a drink elsewhere instead of hanging out in their cozy waiting area. Either way, it's worth the wait.
Osborne Village Cafe
Ditch the insane lines for breakfast at Stella's (although also good) and head here instead. The vintage diner feel is lovely and the food is wholesome, fresh and delicious. They have great vegetarian options too. A true diamond in the rough.
Decent drink options and a simple but great menu make this place a winner. You can really taste the quality ingredients and the dishes are a good value for your money.
This is the place to go for a great burger with a fun twist. My personal favourites are the Shanghai and the Drunken Aussie (an egg on a burger? be still my beating heart). The atmosphere is fun and the glass pop bottles are a nice touch. Skip the upgrade to a bison patty. I love bison, but found this to be on the dry side and much preferred the classic beef.
Burrito del Rio
Chris and I are regular fixtures here for good reason. Hands down the best burritos I've ever had. My favourite is the Vegetarian with guacamole and medium salsa. The result is filling, flavourful and freaking delicious. I'd avoid the chicken though: unfortunately underwhelming. Also, if you opt for one of the Mexican sodas, go with the lime or grapefruit, unless you're down for some maaaajor sweetness.
If sushi's your thing, I love the atmosphere and freshness of the food at Meiji Sushi. Sneak upstairs to G Martini for a girly drink afterward.
Whiskey Bar at The Toad in the Hole
Classic whiskey cocktails like Old Fashioneds and Whiskey Sours (with real egg white) set this place apart from other bars in the area. The 25+ is a bonus for us old fogeys who just want to sit with a good drink and enjoy pleasant conversation.
This is where I go when I'm looking for a nutritious snack or a light meal. The shakes (The Best Green Smoothie in particular) are delicious and super fresh. The same goes for the juice. The KAMP (kale, apple, mint and pineapple) taught me that kale can taste like more than "good for you."
With its "get baked" puns, neon sign, black and white tiling and cherry red tables and chairs, this place is a Winnipeg dessert institution. Spend time perusing the case filled with cake upon cake. (My favourites are the Tia Maria and the Old Fashioned Chocolate Cake.) Slices are reasonably priced and huuuuuge so unless you've got a bottomless sweet tooth, bring a friend or expect to take some home for a sugary snack.
Quality and unusual jewellery with an emphasis on Canadian designers make this place great. This is where I go for a piece I can wear every day - it holds up over time but it's not so precious that I'm afraid to wear it. They also have some pretty cute dresses.
The sister shop to Silver Lotus with an emphasis on shoes. They carry a great selection of offbeat brands and quality materials.
The Happy Cooker
Quality kitchen goods at a range of price options. You'll find some truly high end items alongside more affordable options. If, like me, Julie and Julia made you want to go out and buy some Le Creuset, this is where you find it.
Out of the Blue
Home to some beautiful, vintage inspired clothing options, kitschy items for your home and the cutest change rooms in town (if only they had mirrors!).
Music Trader/Movie Village
The reign of Movie Village has fizzled out, but this is still one of the last places in the city where you can rent movies. They also carry a great rotation of newer music, used CDs, records, and they often have tickets available at the front desk for great local shows.
With original designs and beautiful pieces, this is a great place to go for special occasion or engagement/wedding jewellery.
Vintage in the Village
You're not going to find anything incredibly high quality/rare here, but they've got some cool stuff, the prices are reasonable and the lady behind the counter is the nicest.
I'm a weirdo who enjoys buying souvenir tea towels, so I think this place is awesome. Also great for picking up uniquely Winnipeg tees as souvenirs/gifts for former Winnipegers/to wear somewhat ironically on the streets. (I DID survive the winter of 2013-3014.)
The Osborne Street Bridge
Since its latest update, the Osborne Bridge is both much less dangerous and much more beautiful. Walk across it at night to see the glowing art and poetry. Bonus, monkey around on the bizarre gear statue on the southeast end.