I love Osborne Village. I find it exciting that Winnipeg has such a vibrant and distinctive little strip, ever available to those of us craving a day or night out.
No matter the season, even when it's blistering hot or deathly cold, I can spend an entire afternoon roaming the street. Depending on my mood, I can let my Osborne experience drag into the early and then into the late evening.
I not only shop, but also frequently spend my time on the strip gorging myself with some delightfully decadent meals. I guess it doesn't hurt that many of my personal favourites among the restaurants in the city are all within walking distance in Osborne Village.
It also doesn't hurt that the street itself just seems friendly. When I walk down the strip, most everyone is smiling, and I smile right back.
Even the occasional drifters who are often outside of The Toad in the Hole during the warming months are cheery. They'll usually be holding a sign declaring their love of travel and a large dog will be nestled at their feet.
They seem as much a part of the strip as anyone, and equally as friendly. One time, I accidently dropped my phone out of my bag as I rustled through it during a walk down the strip. A drifter almost immediately called out to me that it had fallen.
When you're on Osborne, it seems everyone is part of a bustling family.
I actually have a tried-and-true "Best Day Ever" Osborne itinerary. I'm sure everyone who frequents the street has his or her favourite haunts, but I want to share mine.
Spend the late afternoon shopping, or at the very least window-shopping. Stores like Desart and Music Trader offer so many extraordinary finds that it can be easy enough to spend the whole day browsing there.
As the evening begins and you begin to get hungry, head over to Segovia. Make sure you get some friends to join you, because the tapas there are all worth trying and, in my opinion, you need to bring enough people to order as many of them as possible.
Since Segovia doesn't take reservations, give them your name and number and they will call you when your table opens. Then head over to Meiji Sushi for some swoon-worthy martinis while you wait for your table.
Afterwards, if you're still feeling like going out -- I am often too full to function after a feast of Tapas, but can sometimes make an exception -- head over to the Toad in the Hole Pub & Eatery and its 25+ whiskey bar. Or head over to Baked Expectations for dessert.
I strongly recommend that you tweak my recommendations to your preferences, and then repeat your Osborne experience as often as necessary.
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