Romance Awaits with Our Guide to the Best Date Ideas in Winnipeg
Sometimes Winnipeg winters can make us want to hibernate. The snow piles up, the wind howls, and suddenly the idea of venturing outside seems about as appealing as a polar bear plunge.
But love doesn’t have to go into hibernation too! Just because the weather outside is frightful, doesn’t mean your date nights have to be.
We’re here to spice things up with some exciting date ideas that will get you out of the house and into the heart of Winnipeg’s vibrant scene.
Whether you’re looking for a cozy escape from the cold or an adventurous way to embrace the winter wonderland, we’ve got you covered.
Romantic Dining Experiences
Have Dinner at 529 Wellington
– Media credit: 529wellingtonwpg
Location: 529 Wellington Crescent
Contact: +1 204-487-8325
Operating hours:
- Monday to Friday – 11:00 AM to 10:00 PM
- Saturday – 4:30 PM to 10:00 PM
- Sunday – 4:30 PM to 9:00 PM
Pricing: $$$
For a date that truly raises the stakes, 529 Wellington offers an experience that’s hard to beat. Known for serving Canada’s top-tier Prime beef, this iconic restaurant allows guests to indulge in their choice of perfectly prepared cuts tailored to their preferred doneness.
But don’t worry if you’re not in the mood for steak – the menu also includes an array of fresh fish and seafood dishes that cater to a variety of tastes.
And for wine lovers, this place is a paradise. With a staggering selection of over 700 wines and a cellar boasting more than 17,000 bottles, it’s no wonder this spot has consistently earned Wine Spectator’s Best of Award of Excellence since 2004.
| Pro Tip: For an extra-special touch, opt for one of the restaurant’s eight intimate dining rooms. Each is designed to offer a unique ambiance. Or, if you’re dining during the warmer months, choose a table on the riverside terrace for a romantic alfresco experience. |
Dine and Sip at Oval Room Brasserie
– Media credit: ovalroombrasserie
Location: 222 Broadway
Contact: +1 204-946-6514
Operating hours:
- Monday to Friday – 6:30 AM to 11:00 PM
- Saturday – 7:30 AM to 11:00 PM
- Sunday – 7:30 AM to 10:00 PM
Pricing: $$$
Nestled in the historic Fort Garry Hotel, the Oval Room Brasserie offers an unforgettable date night where old-world charm meets modern flair.
Led by Chef de Cuisine Kyle Lew, this stylish spot brings classic brasserie and bistro favorites to the table for breakfast, lunch, and dinner, with a menu that feels both familiar and refined.
Expect dishes crafted with care and the finest ingredients, from shareable plates to intimate meals for two, perfect for sparking conversation and savoring each bite.
The setting itself is a romantic blend of elegance and warmth, creating the ideal atmosphere for an intimate evening out.
| Pro Tip: Make sure to explore the extensive cocktail and wine list curated by Wine Director Christopher Sprague. His selections are designed to complement the menu perfectly, adding that extra touch to your meal. |
Indulge in Italian Flavors at Café Carlo
– Media credit: cafecarlo
Location: 243 Lilac St
Contact: +1 204-477-5544
Operating hours:
- Monday to Thursday & Saturday – 5:00 PM to 10:00 PM
- Friday – 11:30 AM to 10:00 PM
- Sunday – 5:00 PM to 9:00 PM
Pricing: $$
Since 1989, Café Carlo has been Winnipeg’s go-to for couples looking for a dining experience that’s both intimate and unpretentious.
This beloved spot is known for its welcoming vibe and menu packed with bold flavors. If you’re looking to impress, start with their famous Fett Chile. It’s a delightful fusion of fettuccine with chicken, chorizo, cashews, and roasted red peppers smothered in a chile cream sauce.
For seafood lovers, the Seafood Cannelloni is a show-stopper in a dreamy herb cream. It’s stuffed with crab, lobster, prawn, bay scallop, and ricotta.
Prefer something light? The Goat Cheese Salad features beets, arugula, and pine nuts, making it a fresh and vibrant choice.
| Pro Tip: Make date night a breeze by reserving your table on their website. Don’t wait to secure your spot – this local favorite fills up fast. |
Adventurous Date Ideas
Go Indoor Rock Climbing at Vertical Adventures
– Media credit: verticaladventures
Location: 77 Paramount Rd
Contact: +1 204-632-5001
Operating hours:
- Monday to Friday – 4:00 PM to 10:00 PM
- Saturday – 11:00 AM to 9:00 PM
- Sunday – 12:00 PM to 7:00 PM
If you’re up for an adventurous date, Vertical Adventures—the city’s first indoor rock climbing facility—is the perfect spot to make it happen.
With over 5,000 square feet of climbing space and routes for every skill level, this gym invites both beginners and seasoned climbers to step out of their comfort zones.
It’s an ideal way for couples to build trust, encourage each other, and enjoy a fun and active experience that’s anything but ordinary.
For just $20, you can grab a day pass, with gear rental available for an extra $5. It will let you try climbing without any long-term commitment.
And if you’re hooked, monthly memberships come in at $80 or $100 with gear included, giving regulars flexibility and great value.
| Pro Tip: Try the “Intro to Climbing” class held every second Thursday to kickstart your climbing journey together. It’s perfect for beginners and covers all the basics, so you’ll feel confident and safe while exploring the walls. |
Test Your Skills at The Real Escape
– Media credit: therealescapecanada
Location: 3137 Portage Ave
Contact: +1 204-615-7717
Operating hours:
- Monday to Saturday – 10:00 AM to 9:30 PM
- Sunday – 9:30 AM to 10:00 PM
Looking for a date idea that’s more than just dinner and a movie? The Real Escape offers the perfect chance to put your problem-solving skills – and your relationship – through a fun, thrilling test.
As the city’s first real-life escape game, this spot lets couples dive into themed adventures. You can enjoy breaking out of “The Pyramid” tomb, hunting down a lost jewel in “The Ruins”, or navigating the medieval halls of “The Castle”.
Each room presents a unique challenge, with puzzles that cater to different interests and skill levels, making it an exciting choice for every pair.
Best part? Each game is designed for groups of four or more, making it a fantastic double-date activity where you can all work together (or maybe compete a little) to beat the clock.
| Pro Tip: Hop over to The Real Escape’s website to book your room in advance. Not only will you secure your spot, but you’ll also get to pick the room theme that suits your vibe. |
Embark on a Hiking Adventure at FortWhyte Alive
– Media credit: fortwhytealive
Location: 1961 McCreary Rd
Contact: +1 204-989-8355
Operating hours:
- Monday to Sunday – 9:00 AM to 5:00 PM
For couples craving a peaceful escape into nature, FortWhyte Alive is an urban oasis sprawling over 660 acres with over 7 kilometers of scenic trails. Winding through prairies, marshes, aspen forests, and lakes, these paths set a serene stage for exploration and quality time together.
Trails are well-maintained and accessible for all fitness levels, with crushed limestone paths perfect for walking, jogging, or biking side by side.
Along the way, you’ll discover unique spots like floating boardwalks through wetlands, a family treehouse, and lookout points ideal for spotting local wildlife.
After a hike, unwind at the Alloway Reception Centre, where The Nature Shop and Buffalo Stone Café await with cozy seating and refreshments.
| Pro Tip: Don’t stop at just hiking – FortWhyte Alive has plenty more to offer for an unforgettable date. Try bird-watching, or take a stroll to the 70-acre bison prairie for a close-up view of these magnificent creatures. |
Cultural Experiences
Admire Art at the Winnipeg Art Gallery
– Media credit: wag_ca
Location: 300 Memorial Blvd
Contact: +1 204-786-6641
Operating hours:
- Wednesday to Sunday – 11:00 AM to 5:00 PM
Established in 1912, the Winnipeg Art Gallery (WAG) is Canada’s oldest civic art gallery, boasting an impressive collection of over 27,000 artworks.
It’s also home to the world’s largest public collection of contemporary Inuit art, making it a must-visit for art-loving couples.
With exhibitions catering to diverse tastes, current highlights include “Riopelle: Crossroads in Time”. The exhibit celebrates Canadian artist Jean-Paul Riopelle, and “Inuit Sanaugangit,” an exploration of Inuit art from 200 BCE to today—a journey through history and culture.
Beyond the exhibits, WAG hosts programs that make art accessible and engaging. Their “Canada Life Free Sundays@WAG” offers free admission on the second Sunday of every month, perfect for couples who want a cultured date on a budget.
| Pro Tip: Don’t miss WAG’s signature events, like the “CRAFTED 2024 Show + Sale.” This annual event features handmade goods from local artisans, giving you a unique shopping experience right in the heart of an artistic setting. |
Catch a Show at the Burton Cummings Theatre
– Media credit: theburtwpg
Location: 364 Smith St
Contact: +1 204-987-7825
The Burton Cummings Theatre is a date night gem in the heart of Winnipeg’s cultural scene. Since its days as the Walker Theatre in 1907, this iconic venue has hosted a century’s worth of captivating performances.
With just 1,600 seats, the theater creates a cozy and up-close vibe. This makes every concert, comedy show, or theatrical production feel like it’s just for you two.
Whether you’re catching country stars like Tenille Townes and Carly Pearce or getting swept up in something quirky like “HYPROV: Improv Under Hypnosis,” there’s always something to suit your mood.
| Pro Tip: Snap up your tickets early – shows here tend to sell out fast. Grab them through the official website to secure your spot for an unforgettable night under the theater lights. |