Ultimate List of Date Night Ideas in Winnipeg (2024)

An image of a woman and a man laughing at an intimate joke while on a date.

Looking for fun date night ideas in Winnipeg? We’ve got you covered! Whether you’re into adventurous activities or painting the town red, this list covers it all. Be sure to come back often as we’ll update this list regularly.

Jump to: Fun | Cheap and Free | Extending Date Nights

Fun Date Ideas in Winnipeg

Catch a sports game

If you’re a hockey fan and you’re from Winnipeg, catching a hockey game at the Canada Life Centre (formerly Bell MTS Place) is an obvious choice! Winnipeg is the home of the Winnipeg Jets and the Manitoba Moose, and we love our teams.

If you’ve never been to a game before, be prepared to be amazed by the energy and excitement you can feel from the fans.

A Goldeyes Game I attended with my husband at the Shaw Park in 2021.
A Goldeyes Game I attended with my husband at the Shaw Park in 2021.

And if hockey isn’t so much your thing, why not catch a Goldeyes game at the Shaw Park? It’s a great way to spend time outdoors during the spring/summer months, and when the game’s done, Downtown Winnipeg is just a short walk away.

Check out live events

A picture of Iron Maiden performing in Winnipeg back in 2019 during their Canadian tour.
Iron Maiden performing in Winnipeg back in 2019

If you’re into live music, you’ll find plenty to do in Winnipeg. The main concert venue is the Canada Life Centre (formerly Bell MTS Place) for big pop acts like Iron Maiden, but there are many other places to catch a show, including the Centennial Concert Hall, Burton Cummings Theatre, Park Theatre, and the High & Lonesome.

Activate your game face

Are you more of an “active date” person? Well, you’ve got plenty to choose from in Winnipeg!

The outside storefront of Activate Games in Winnipeg during winter.

Activate Games is an active gaming facility, where you’ll move between different interactive rooms and play arcade-style games by jumping, running and dodging! Perfect for double dates with your new beau, since you’ll need a group of 3+ to conquer them all.

There are plenty more fun places for VR games, escape rooms and arcade games in Winnipeg that to list them all out would require another post!

Address: 3338 Portage Ave, Winnipeg, MB R3K 0Z1

Spend the day at the Forks

An image of the Winnipeg signage in front of the Canadian Museum for Human Rights at the Forks.

The Forks is one of our most beloved tourist spots, and for good reason! There are tons to do here for everyone at this historic meeting spot.

You can have your pick of delicious meals from the food market (I highly recommend the Taste of Sri Lanka), explore the shops selling local and handmade goods, and take in the scenery with a riverside walk.

If you’re looking for a little more fun, check out the Phantom Amusement Arcade for some pinball action, or head to the outdoor patio to while away the summer night with flights of beer (or wine!) and food.

More into history? The Forks has a one-hour self-guided audio tour where you can learn more about the importance of this river meeting spot and its history spanning 6,000 years!

Parking is only $2 an hour.

Go on a ghost tour of Winnipeg

Winnipeg was settled as a city in 1873, so that means it has a long history and many interesting historical buildings that have quite a few hauntings associated with them.

If that sounds up your alley, check out The Trolley of Terror, where the Midnight Conductor will take you around on a journey to discover Winnipeg’s darkest and most haunting history!

Fun fact: Did you know that Arthur Conan Doyle visited Winnipeg in 1923 to participate in a séance with Dr Thomas Glendenning Hamilton?

Skate the frozen Red River Trail 

There’s no better way to experience Winnipeg’s winter wonderland than by taking part in our annual tradition of skating down the world’s longest naturally frozen skating trail (Guinness World Record, baby!).

People skating down the Red River Trail in Winnipeg near the Forks.
An old picture from 2021 of people skating down the Red River Trail in Winter!

It’s the perfect way to get a little closer to your beau – if your date’s not a confident skater, you can hold their hands to keep them steady. Don’t forget to get hot chocolate for the ultimate date finisher!

Pro tip: Make a tradition that’s just between the two of you by going out on a date to pick the perfect Christmas Tree!

Discover the occult mysteries behind Manitoba’s most unique architecture landmark

An image of the park next to the Manitoba Legislative Building, with the Golden Boy on the very tip of the building.

If you’ve ever passed the Manitoba Legislative Building, you might have had a few questions. Have you ever wondered who the Golden Boy was, or why there were sphinxes on the roof? Or that there are hidden symbolisms in every aspect of the way the building was constructed? Go on the Hermetic Code Tour to learn more about one of Winnipeg’s most intriguing and mysterious landmarks for more than 100 years.

Fun fact: Did you know the Hermetic Code Tour is one of few tours promoted internationally by Destination Canada?

Go on a brewery tour

There are over 20+ breweries in Winnipeg, and while some of the city’s better-known ones have their own tours, you can also book a private tour with any of them.

Kilter Brewery in St Boniface, Winnipeg. A must visit if you love tasting flights of beer!
Kilter Brewery in St Boniface, Winnipeg. A must visit if you love tasting flights of beer!

Some taprooms can be gastronomical experiences of their own—One Great City, in particular, has pretty amazing food to pair with your tasting flights!

Cheap Date Night Ideas in Winnipeg (and some free ones!)

If you’re into cheap dates (and are you really a Winnipegger if you’re not?), one of my favourite things to do is to explore Winnipeg.

It’s free, you get to see a different side of Winnipeg together, and exploring new places together is another way to strengthen budding relationships!

Here are some great places to check out for a cheap date night in Winnipeg.

Go on an ice cream date

A classic but a goodie, you really can’t go wrong with this. Sargent Sundae’s been around since 1984 and it is a hotspot (even in fall!) for Peggers looking for a tasty treat.

Once you’ve got your goodies in hand, cross the bridge to take a walk in Assiniboine Park and try to finish it before it melts all over you!

A big ice cream cone from BDI, the Bridge Drive-In, in front of the iconic bridge.
This was a monster of an ice cream from BDI!

Another iconic ice cream place that’s got to be mentioned is BDI, also known as the Bridge Drive-In. They’ve been around for over 60 years and walking across the Elm Park Bridge (that BDI took its name from) with one of their specialty cones is an essential Winnipeg summer experience. (BDI menu here)

Explore the Exchange District on First Fridays

The Exchange District is one of Winnipeg’s most iconic neighbourhoods, with over 150 historical buildings that have been built between 1880 and 1920.

There’s a ton to see here, from cute little shops selling handmade products, restaurants, art galleries, and board game cafes to lifestyle shops. Check them out on the First Fridays of every month.

Go on a Christmas Lights show hunt

Get some peppermint mocha and put on the radio for some festive tunes as you drive around looking for the house with the best decorated Christmas lights!

A fully decorated house with an LED Christmas Tree, singing snowmen and flashing lights.

It’s a fun and cheap date we do during winter time ourselves. You get to see some really cool houses who have LED trees and singing snowmen, and the decorated trees really add to a festive mood.

Check out our list of the best drive-through and walk-through Christmas Lights shows in Winnipeg!

Take a hike on one of Winnipeg’s numerous trails

An image of the bridge in Woodhaven Park in the St James neighbourhood.
Woodhaven Park in St James

Winnipeg has some fantastic hiking opportunities for exploring nature, and the best part is that you don’t need any special skills to enjoy them.

All you need is to dress right for the weather, put on your favourite walking shoes and bring water on your trek. With over 1000 parks in Winnipeg, you can find a trail to suit your needs.

Pack a picnic and spend the day outdoors

This is very much an outdoors summer activity. Going on a picnic is a great way to spend time together with your beau without spending a lot of money.

Just pack up your favourite foods, get a picnic mat from the dollar store (or a bougie one from Winner’s), and you’re all set!

Explore Winnipeg on “A Sleepless Night” during Nuit Blanche

Red, Green, Blue by Khan Lee, provided by Manitoba Culture Days

Nuit Blanche first started in Winnipeg in 2010, but it’s been a staple event ever since!

Nuit Blanche, which means “A Sleepless Night”, is a free nighttime exploration event spanning several neighbourhoods like St. Boniface, Downtown, the Exchange District, The Forks and the West End.

There are usually many art exhibits and things to check out, and it showcases Winnipeg in a different light! Nuit Blanche usually takes place last Saturday of September or the first Saturday of October.

Explore flea markets for some “antique” pursuing

There are lots of flea markets around Winnipeg, and they’re a great place to find vintage finds, antiques, collectibles, and anything else you can imagine.

Even if you are there just to browse, there’s plenty to see. Some have unique handmade items (like hand-turned pens), forgotten collector’s comics, cheap DVDs, discount Xbox games, and unique kitsch that shows off Winnipeg’s history!

Extending your Date Night after Dinners

If you’re both feeling good and the vibe is right, sometimes you just don’t want the night to end after a romantic dinner. Why not extend your date night with some of these ideas we have for you?

Luxuriate in an immersive movie experience at Grant Park

One of Winnipeg’s not-so-well-kept secrets, Landmark Cinemas at Grant Park features reclining leather seats that’ll give you that full-blown immersive movie experience.

The leather seats in the Landmark Grant Park can recline with the touch of a button, and you can also lift the divider between two seats.

Pro-tip: Lift the dividing armrest between you and your date so you can scoot a little closer and snuggle up!

Check out a live comedy show

Laughing is one of the best ways to bond with another person, so why not get some good ol’ belly-aching laughs at the Rumours Comedy Club?

It’s the perfect way to see if your sense of humour meshes up! Past guests include the likes of Norm Macdonald, Chris Locke and more. Tickets start from $14. 

Bop to live music 

It may not be obvious if you’re not looking for it, but Winnipeg has a thriving live music scene. Check out the Good Will Social Club or the High and Lonesome Club (both in the heart of downtown) for a good time and reasonably priced drinks.

The Italian band Goblin, performing at the Park Theatre in Osborne for the 45th anniversary screening of Suspiria.

The Park Theatre in Osborne also regularly brings in amazing musical acts like Goblin (pictured above), who recently performed the score along to Suspiria for the film’s 45th anniversary.

Catch a Shakespeare play in the ruins of St Norbert’s 

If live theatre is your idea of romantic, check out the performances that Shakespeare in the Ruins performs every spring. Staged in the ruins of an 1890s church with stone walls where both audience and actors can interact, this unique experience is a surefire way to capture the heart of your date!

Play at a board games cafe

Playing board games is a great way to bond with your beau, and what better way to do it than at a board games cafe with delicious food and drinks? Across the Board in downtown is a Winnipeg favourite with its massive board game library that’s sure to have something for everyone.

Know of something awesome that we’ve missed out? We’re always on the hunt for more great ideas, so help us make this list even better by contacting us


As a newly transplanted Canadian who married a local Pegger, my goal with We Are Winnipeg is to explore everything Winnipeg and Manitoba has to offer!

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