Jaclyn’s guidebook
Where to eat - Osborne Village
These are our favorite restaurants within an easy walk.
A beautiful, upscale, Spanish tapas restaurant. The perfect spot for a romantic date or an intimate girls' night out. Segovia's does not take reservations but will take your phone number and call you when a table is ready. Head there early, put your name on the list, and grab a cocktail elsewhere in Osborne Village as you wait!
39 locals raden deze aan
Segovia Tapas Bar & Restaurant
484 Stradbrook AveA beautiful, upscale, Spanish tapas restaurant. The perfect spot for a romantic date or an intimate girls' night out. Segovia's does not take reservations but will take your phone number and call you when a table is ready. Head there early, put your name on the list, and grab a cocktail elsewhere in Osborne Village as you wait!
The place for brunch in Osborne Village. Stella's is a casual, local chain with fresh baked breads, fabulous home-made soups, and some of the best pancakes in the city. Try the chorizo hash or the guacamole BLT with the house salad, two of my favorite items on the menu!
22 locals raden deze aan
Stella's Osborne Village
166 Osborne StThe place for brunch in Osborne Village. Stella's is a casual, local chain with fresh baked breads, fabulous home-made soups, and some of the best pancakes in the city. Try the chorizo hash or the guacamole BLT with the house salad, two of my favorite items on the menu!
A trendy spot with a little something for everyone! Open until 2 am, the Cornerstone serves a full menu (appetizers, a pasta and a quiche of the day, sandwiches) and delicious cocktails even late. Justin and I love the steak bites.
19 locals raden deze aan
The Cornerstone Bar & Restaurant
93 Osborne StA trendy spot with a little something for everyone! Open until 2 am, the Cornerstone serves a full menu (appetizers, a pasta and a quiche of the day, sandwiches) and delicious cocktails even late. Justin and I love the steak bites.
Fabulous, healthy burgers from a local spot that cares about the environment. The cheeky burger names, the black and white decor, and the unique table "numbers" make Nuburger a cool place to check out!
32 locals raden deze aan
Nuburger
472 Stradbrook AveFabulous, healthy burgers from a local spot that cares about the environment. The cheeky burger names, the black and white decor, and the unique table "numbers" make Nuburger a cool place to check out!
Where to drink - Osborne Village
Osborne Village has so many late night spots to choose from! These are our recommendations.
Arguably the best craft cocktails in the city. A true speak-easy vibe tucked away in the Osborne Village. The interior of this French restaurant and bar is incredible - wallpapered with the pages of antique cookbooks and featuring dripping candles - and the menu changes often. Go for the inventive cocktails; they are ridiculously good and worth every penny.
14 locals raden deze aan
Sous Sol
22-222 Osborne StArguably the best craft cocktails in the city. A true speak-easy vibe tucked away in the Osborne Village. The interior of this French restaurant and bar is incredible - wallpapered with the pages of antique cookbooks and featuring dripping candles - and the menu changes often. Go for the inventive cocktails; they are ridiculously good and worth every penny.
The spot in Osborne Village for a casual beer, a relaxed bite to eat, or a game of pool. A staple in the Village for decades, you can spot patrons of all ages relaxing with a drink by day.
The attached, often busy, Whiskey Bar (particularly popular with 20 and 30-somethings) is the spot for an Old Fashioned or a fabulous Whiskey Sour. Great for a group of friends any night of the week.
On the weekends, the downstairs (named the Cavern) often features live music. The Cavern is jam packed on Tuesday nights, where sometime after 11:00 Soul Night begins. Expect a sweaty dance party if you choose to visit!
41 locals raden deze aan
The Toad in the Hole
155 Osborne StThe spot in Osborne Village for a casual beer, a relaxed bite to eat, or a game of pool. A staple in the Village for decades, you can spot patrons of all ages relaxing with a drink by day.
The attached, often busy, Whiskey Bar (particularly popular with 20 and 30-somethings) is the spot for an Old Fashioned or a fabulous Whiskey Sour. Great for a group of friends any night of the week.
On the weekends, the downstairs (named the Cavern) often features live music. The Cavern is jam packed on Tuesday nights, where sometime after 11:00 Soul Night begins. Expect a sweaty dance party if you choose to visit!
Tucked away, this martini bar serves an incredibly impressive list of complex and creative martinis. A great spot for a night out with friends or a drink after dinner!
8 locals raden deze aan
G Martini Bar
454 River AveTucked away, this martini bar serves an incredibly impressive list of complex and creative martinis. A great spot for a night out with friends or a drink after dinner!
The most popular dance club in the area and maybe even in the city - Upstairs is the place to dance after 10:00 on Friday and Saturday nights. The club attracts primarily a younger crowd and features a large dance floor and ample outdoor space. The DJ plays top hits and favorites from the 90's all night long.
34 locals raden deze aan
Upstairs in the Village
206 Osborne StThe most popular dance club in the area and maybe even in the city - Upstairs is the place to dance after 10:00 on Friday and Saturday nights. The club attracts primarily a younger crowd and features a large dance floor and ample outdoor space. The DJ plays top hits and favorites from the 90's all night long.
Where to shop - Osborne Village
The Village is a boutique shopper's dream. Trendy women's clothing stores, interesting local specialty shops (pet supplies! kitchen ware!) are an easy walk away. Here are some of our recommendations.
HUSH Clothing & Accessories
555 Sterling Lyon PkwyA beautiful boutique store for modern clothing and trendy dresses.
Silver Lotus
103 Osborne StStunning, modern, reasonably priced jewelry fill Silver Lotus!
Do you love to cook? This shop has every tool and every gadget to make you a master chef!
The Happy Cooker
464 Stradbrook AveDo you love to cook? This shop has every tool and every gadget to make you a master chef!
Worth the drive - Our favorites a short drive or cab ride away
Some spots are worth checking out - despite the cab fare or the (very) long walk.
Pizzeria Gusto
404 Academy RdThe Merchant Kitchen
314 Donald StRed Ember Common
1 Forks Market RdMáquè
909 Dorchester AveMad About Style Boutique
538 Academy RdLeopold's Tavern Winnipeg Osborne
696 Osborne StCoal & Canary
1 Forks Market Rd