V-Day in the village
Valentine’s Day 2026 is coming up and Osborne Village has options. We’ve rounded up events, specials, and date-night ideas for couples, friends, and families to help you make the most of the weekend.
Experience a VALENTINE’S DAY
HONEYMOON DESTINATION TRIP IN THE ISLANDS (in winnipeg) -
PRIX FIXE 4 COURSE MEAL FOR TWO
Experience the taste of the islands right in the heart of Osborne Village 🏝️ Featuring live music from James Buckboro
When: Saturday, Feb 14th | Resos available 6pm-11pm
Where: Must Be The Place | 484 Stradbrook Ave
Cost: $65 for two
To reserve: Contact via Instagram DM or in-person @mustbetheplacewpg
i: Spam Fries served with sriracha mango sauce
ii: Ahi Tuna Tostada. Ahi tuna, avocado crema, salsa macha, topped with green onions on toasted corn tortilla
iii: Smoked Kalua Pork Belly. Smoked pork belly hawaiian style, served with savoury sticky coconut rice
iv: Upside Down Pineapple Cake. Served with caramel rum sauce.
See a comedy show -
The Snowed In Comedy Tour: A Night of Laughter and Fun
Four international comics. One stage. A blizzard of laughs. Critics call it “Better than the Just for Laughs Tour” and “A Flurry of Laughs You Can’t Miss.”
When: Friday, Feb 13th | 7:00PM
Where: Gas Station Arts Centre | 445 River Ave
Cost: $50.00
Duration: 60 minutes. Doors open 45 minutes before the show. No entry once it starts.
Ticket Link: https://www.jumpcomedy.com/e/prince-rupert-clone-2
Experience classical romance -
Candlelight: Valentine’s Day Special
Candlelight concerts are a live, multi-sensory musical experience under the gentle glow of candlelight. String Quartet: 2 violins, 1 viola, 1 cello.
When: Friday, Feb 13th | 8:45PM
Where: Crescent Arts Centre 525 Wardlaw Ave
Cost: Price ranges from $62.50 - $96.50
Duration: 60 minutes. Doors open 45 minutes before the show. No entry once it starts.
Ticket Link: https://feverup.com/m/429076
Age recommendation: The experience is recommended for those who are 8+. To preserve the experience, disruptive behaviour may result in being asked to step outside. Anyone under the age of 16 must be accompanied by an adult.
Get a Treat at Baked Expectations 🍰
Stop by with your sweetie for a sweet treat. Baked Expectations will be decorated for Valentine’s day and is open for dine-in and delivery with delicious cakes, tortes, and hot drinks.
Where: Baked Expectations | 161 Osborne St
Baked Expectations Hours:
Monday | 12–10 PM
Tuesday | 12–10 PM.
Wednesday| 12–10 PM
Thursday | 12–10 PM
Friday | 12-11 PM
Saturday | 12-11 PM
Sunday | 12-10 PM
Celebrate with a CHERRY HEART CRULLER🍒💖
Stop by Crumb Queen or Little Sister on Valentine’s day for a Cherry Heart Cruller (Sour cherry crullers are available all week but only heart shaped on Feb 14)
Where: Crumb Queen 166 Osborne St Unit 2 / Little Sister Coffee Maker 470 River Ave
Crumb Queen Hours:
Wednesday | 8:30 AM–3PM
Thursday | 8:30 AM–3PM
Friday | 8:30 AM–3PM
Saturday | 8:30 AM–3PM
Sunday | 8:30 AM–3PM
Have a Date Night at Cleocatra
Cleocatra is a vintage-style cat cafe with cozy seating, delicious drinks, and desserts. Book a visit to the cat room and possibly adopt a new furry friend.
Where: Cleocatra Cafe | 106 Osborne St
Cleocatra Hours:
Mon – Thurs | 12PM – 8PM
Fri- Sun | 9AM – 10PM
To Reserve: https://cleocatracafe.as.me/schedule/17a4f2d9
Ditch the traditional valentine’s day plans -
I ❤️ U but I've Chosen Techno
“I ❤️ U but I've Chosen Techno” is a mix of Old School / New School techno featuring: Nathan Zahn, Nikki Volan, JR Ragoo, and Dray. Presented by Symptoms Technologies.
Where: Club Happenings | 114b Osborne St
When: Feb 14th | 9pm - 2am
Cost: $20
Ticket Link: https://www.universe.com/events/696729f2234ec200243dae23
Dance the night away -
Fuego Latin Nights: Valentine’s Edition
Fuego Latin Nights is Winnipeg’s newest Latin event bringing you all your favorite hits from Salsa to Bachata to Kizomba tunes, old school classics to the hottest new tracks. Featruing Latin DJs: DJ China Loca, DJ Cuban Baby, and DJ Canchito. PLUS a special live band performance by Winnipeg's newest Cuban band.
Where: Encore Lounge - 206 Osborne Street
When: Friday February 13 | Doors Open 8:30pm
Theme: Pink, red or white!
Cost: $15 in advance | $20 at the door
Ticket Link: 3common.com/fuego-latin-night
Buy flowers for your valentine FROM
sMALL mERCIES
Shop fresh cut & dried bouquets at Small Mercies. Pre-order option available.
Where: Small Mercies - 111 Osborne St
Cost: Price varies
Order Link: www.smallmercies.co
Have a romantic dinner at
Sous Sol
Although reservations for Feb 14th are fully booked, Feb 13th offers the same Valentine’s Day prix fixe menu.
Where: Sous Sol | 22-222 Osborne St
Cost: $95 per person
To Make a Reservation: www.soussolosborne.com/reserve