The Best Things to Do in Winnipeg: A 2-Day Guide
- Lyn (aka Jazz)
- 3 days ago
- 11 min read
Mention Winnipeg to many Canadians, and they'll likely think of two things: the dead centre of the country and famously cold winters. However, as someone who has visited on multiple trips, I'm here to tell you that this city, situated where the Red and Assiniboine Rivers meet, is so much more than a flyover (or drive-through) province. It's a place of deep, complex history, a resilient and unpretentious spirit, and a vibrant cultural scene.
This is my personal guide to a city that has consistently surprised me with its depth and creativity every time I visit. I've distilled my experiences—from quick stops to a deeper dive on my solo cross-Canada road trip—into this ultimate 2-day itinerary. We'll explore the best of Winnipeg, from its most iconic landmarks to the historic streets that reveal its layered, fascinating story. If you're ready to discover the true heart of Canada, let's get started.
Table of Contents
Winnipeg's Geography & Climate
Winnipeg is spread across a famously flat prairie expanse at the confluence of the mighty Red and Assiniboine Rivers, and has been a meeting place for millennia. This flat terrain, once the bottom of ancient Lake Agassiz, gives way to the endless, dramatic skies that the prairies are famous for. While it serves as the gateway to the Canadian Shield to the east, the city itself is a true prairie metropolis, its grid laid out under a vast, open sky.
Winnipeg is a city of four distinct and dramatic seasons. Winters are undeniably cold—and that's an understatement—but they are also often dry and brilliantly sunny. Winnipeggers embrace this, building a skating trail on the frozen rivers and celebrating with festivals. In sharp contrast, the summers are hot, sunny, and wonderfully vibrant, with long prairie evenings where the sun doesn't set until late in the evening. Spring and autumn are fleeting but beautiful, offering a colourful and refreshing break between the two extremes.
Winnipeg's History & Culture
To understand Winnipeg, it is essential to understand its history, which dates back long before its colonial era. This land is Treaty 1 Territory, a traditional gathering place for Anishinaabeg, Cree, Oji-Cree, Dakota, and Dene Peoples, and the homeland of the Métis Nation. For over 6,000 years, the junction of the two rivers—known as The Forks—was a vital centre for trade, ceremony, and community. This Indigenous legacy is the foundational layer of the city's identity.
The arrival of European fur traders established key posts, such as Fort Rouge and Fort Garry. With the arrival of the railway, Winnipeg exploded into a "Gateway to the West," a boomtown of staggering wealth and rapid growth, which is preserved in the stunning architecture of the Exchange District. But this history also includes deep-seated conflict and a legacy of civic action, most notably the 1885 Northwest Rebellion and the 1919 Winnipeg General Strike. This resilient, layered, and often complicated past has forged a unique cultural character: unpretentious, diverse, and fiercely creative. Today, Winnipeg is a powerhouse for the arts, home to the Royal Winnipeg Ballet, the Winnipeg Symphony Orchestra, a thriving independent music scene, and a culinary world that reflects its multicultural fabric.
Winnipeg: More Than Just a Stop on a Cross-Canada Road Trip
I've passed through Winnipeg on my drives across the country, but my most recent stop during my Solo cross-Canada road trip really cemented my love for this city. It's easy to see it as just a midway point, but I've always felt there was more to it. This year, I finally took the time to peel back some of its layers, confirming what I'd long suspected: Winnipeg isn't a place to pass through; it's a destination in its own right.
This post is the deep dive I promised in my Manitoba road trip post, where Winnipeg was a key part of that larger prairie experience. To me, it truly feels like a city of layers—of history, resilience, and creativity, all built upon one another. It's unpretentious, but with a depth that rewards anyone willing to stop and explore, and that's exactly what I want to share with you.
Getting Around Winnipeg
Winnipeg is a prairie city, which means it's quite spread out, but don't let that intimidate you. The city's core is remarkably walkable, and I've designed Day 1 of this itinerary so you can park your car (or walk from your hotel) and explore entirely on foot. The Forks, the Canadian Museum for Human Rights, Upper Fort Garry, and the Exchange District are all within a pleasant walking distance of each other. For Day 2 attractions, such as Assiniboine Park, your best options are to use Winnipeg Transit (the city's bus system; purchase a Peggo card for easy payment) or a ride-sharing service like Uber. A car is definitely helpful for maximizing your time on Day 2, but it's not strictly necessary if you plan your bus routes effectively.
The Ultimate 2-Day Winnipeg Itinerary
I've organized this 2-day guide to be as logical as possible, clustering attractions to maximize your time and minimize travel. Here’s how I’d spend a perfect 48 hours in Winnipeg.
Day 1: History, Human Rights, and Historic Streets
Get ready to lace up your walking shoes! Day 1 is all about exploring Winnipeg's historic and modern core on foot. I've designed this route to be completely walkable, allowing you to park your car and immerse yourself in the city's foundational sites. I found reasonable parking at the Fork Market and spent the rest of my day exploring on foot.
This guide begins at the city's ancient gathering place and then delves into powerful stories of human rights, concluding by wandering the streets of a perfectly preserved boomtown.
The Forks National Historic Site & Riverside Walk
The Forks National Historic Site is far more than just a market (which we'll get to later); it's the very heart of the city, a historic and sacred gathering place for over 6,000 years, situated at the confluence of the Red and Assiniboine rivers.
Before you head into the market bustle, I highly recommend taking a walk along the Riverside Walk. This beautifully maintained trail system provides a genuine sense of the prairie landscape and the power of these two mighty rivers. As you stroll, you'll encounter extensive, beautifully designed interpretive panels that share the deep history of this land—from an Indigenous trading and ceremony site to its later role as a key hub in the fur trade. You'll also find peaceful green spaces, sculptures, and lookouts offering a perfect view of the Esplanade Riel bridge and the Saint-Boniface Cathedral across the water.
Once you've explored the river's edge, turn your attention to the grounds of the Historic Site itself. The area is dotted with more sculptures, gardens, and interpretive displays that chronicle its 6,000-year history. A must-see is the Oodena Celebration Circle, a powerful and beautiful site designed to honour the area's Indigenous heritage. This natural, bowl-shaped amphitheatre features star charts, a sundial, and ceremonial sculptures, serving as a modern space for reflection and celebration on ancient, sacred ground.
Another key stop is the 'Wall Through Time,' which physically illustrates the different layers of history, from the original Indigenous settlement through the fur trade, railway, and immigration eras. Taking the time to explore these free, outdoor exhibits provides context for the entire city, long before you even step inside a building or museum.
Address:Â 1 Forks Market Rd (The Forks)
Cost:Â Free (outdoor site)
Hours:Â 24/7 (grounds)
Canadian Museum for Human Rights (CMHR)
The Canadian Museum for Human Rights (CMHR) is an experience that will stay with you long after you leave. The building itself is an architectural masterpiece and a profound metaphor. You begin in the dark, cavernous 'Roots' section, then physically ascend through the building on a series of glowing alabaster ramps—a 'Journey to Light'—that leads you through the main galleries. The journey culminates in the sun-filled 'Cloud' and the 'Tower of Hope,' which offers a panoramic (and hopeful) view of the city.
Inside, the exhibits are equally powerful and deeply thought-provoking. This is not a passive museum of artifacts; it's a museum of stories. The galleries, including the Indigenous Perspectives hall and the Canadian Journeys gallery, use cutting-edge technology and personal testimony to explore human rights struggles, tragedies, and triumphs both in Canada and around the world. Be prepared: the exhibits are unflinching and can be emotionally heavy, but they are handled with immense care.
It is an essential stop for anyone visiting Winnipeg, and I recommend allocating at least 2-3 hours for your visit. Rushing this experience would be a disservice to yourself and to the stories held within. It’s a place for reflection and learning.
Address:Â 85 Israel Asper Way
Cost:Â $22/$17/$17 (Adult/Youth/Senior)
Hours:Â Check website - typically closed on Mondays
The Forks Market
After the emotionally powerful experience at the CMHR, you'll be ready for a lively break and some amazing food. Walk back to The Forks Market, which is housed in historic buildings that once served as stables and rail yards. Today, it’s a bustling, energetic public market packed with an incredible array of local food vendors. Whether you're craving handmade pierogies, fresh pasta, spicy curry, or artisanal pastries, you’ll find it here. The upper level also features a variety of local makers and shops, making it perfect for browsing unique souvenirs.
Once you've grabbed your food, the next stop is The Common. This is the market's fantastic central bar, and it's what makes the whole dining experience so unique. Instead of being tied to one restaurant's drink list, you can bring your food from any vendor and pair it with a drink from their massive, curated selection of local and regional craft beer on tap, plus a great list of wines. The communal tables create a vibrant, social atmosphere, making it the perfect spot to refuel, relax, and soak in the local vibe.
Address:Â 1 Forks Market Rd
Cost:Â Prices vary by vendor
Hours:Â Typically 7 am - 10 pm, but check website
Upper Fort Garry Provincial Park
A short walk from The Forks, this park preserves the remaining gate of the original Upper Fort Garry. It's the birthplace of Manitoba. The highlight is the futuristic, high-tech heritage wall, which uses sound and light to display the outlines of the long-gone fort buildings. It's a fantastic blend of old and new. It won't take a lot of time to explore, but it is well worth including.
Address:Â 130 Main St
Cost:Â Free
Hours:Â 24/7
The Exchange District
To cap off your first day, head into my favourite neighbourhood in the city: the Exchange District. This sprawling 20-block area is a designated National Historic Site and feels like stepping directly into the past. It’s home to North America’s most extensive and best-preserved collection of turn-of-the-20th-century 'Chicago-style' architecture, from Winnipeg's 'boomtown' era when it was the 'Gateway to the West.'
The heart of the area is Old Market Square with its futuristic stage, but the real joy is getting lost in the grid of cobblestone streets and heritage facades. You'll wander down streets like Bannatyne and McDermot (often called the 'most beautiful' in the city), marvelling at the terracotta and stone buildings that once housed the nation's banks, grain exchanges, and warehouses. Today, these historic spaces have been reborn. They now house a vibrant community of independent boutiques, unique design shops, art galleries, and some of the city's best coffee shops (like Parlour Coffee) and restaurants.
You can easily explore on your own, or if you're curious about the stories behind the stunning facades, you can download a self-guided audio tour from the Exchange District BIZ website. This is the perfect place to grab a coffee, browse for a locally-made souvenir, and admire the architecture that tells the story of Winnipeg's ambitious, wealthy, and complex past.
Address:Â (Neighbourhood) Main St & Bannatyne Ave
Cost:Â Free to walk
Day 2: Art, Parklands, and French-Canadian Roots
After a packed first day exploring Winnipeg's walkable core, Day 2 is all about venturing a little further to experience the city's other incredible layers. Today, you'll need a car or a bus pass to explore world-class art and history, relax in one of Canada's most beautiful urban parks, and discover the unique Francophone culture of Saint-Boniface.
Manitoba Museum
This is the classic Winnipeg museum for a reason. It's a fascinating journey through Manitoba's history, from the time of the dinosaurs to the present. The two most iconic exhibits are the full-size replica of a 17th-century ship, the Nonsuch, and the 1920s Winnipeg street scene that you can walk through. It's pure magic. Check the website for special evening events.
Address:Â 190 Rupert Ave
Cost:Â $24/$21/$18 (Adult/Senior/Youth All Attractions Pass)
Hours:Â Check the website for hours. Closed Mondays.
WAG-Qaumajuq
If you're more of an art lover, I highly recommend visiting the Winnipeg Art Gallery and the new, breathtaking Qaumajuq centre. Qaumajuq houses the world's largest public collection of contemporary Inuit art. The 'Visible Vault,' a three-storey glass structure, is worth the price of admission alone. It's stunning.
Address:Â 300 Memorial Blvd
Cost:Â $18/$15/Free (Adults/Seniors/Youth & Indigeneous Peoples)
Hours:Â Check website - closed Mondays & Tuesdays
Assiniboine Park
Time to head to Winnipeg's 'green lung.' Assiniboine Park is massive and beautiful. You can't do it all, so I recommend two highlights: the Leo Mol Sculpture Garden (a serene, free garden full of gorgeous art) and The Leaf, a new and incredible horticultural attraction with four distinct biomes. If you have kids (or love animals), the Assiniboine Park Zoo and its 'Journey to Churchill' polar bear exhibit is world-class.
Address:Â 55 Pavilion Crescent
Cost:Â Park/Sculpture Garden is Free. The Leaf and the Zoo have separate admission fees.
Hours:Â Park is open daily. Check hours for The Leaf/Zoo.
Saint-Boniface
From Assiniboine or downtown, head across the river to Winnipeg's vibrant French Quarter. The best way to get there from The Forks is by walking across the beautiful Esplanade Riel pedestrian bridge. The highlight is the Saint-Boniface Cathedral-Basilica. The stunning 1908 facade is all that remains after a fire, and it stands today as a memorial, with a modern church built behind it. It's incredibly photogenic.
Address:Â 180 Av. de la Cathedrale
Cost:Â Free to visit the grounds and facade. Donations welcome.
Louis Riel National Historic Site
To truly understand the story of Manitoba, you must understand Louis Riel. He was a Métis leader and the 'Father of Manitoba,' who led two resistance movements to protect the rights, land, and culture of his people as the Canadian government expanded west. His story is complex, passionate, and central to the province's entry into Confederation. While he was controversially executed for treason in 1885, he is now recognized as a key figure in Canadian history, and his grave can be visited in the cemetery at the Saint-Boniface Cathedral.
To connect more deeply with his story, I highly recommend a visit to the Louis Riel National Historic Site. Located a short drive south of Saint-Boniface in the St. Vital neighbourhood, this site preserves the heart of the 19th-century Red River Métis community. Here, you'll find the home of his mother, Julie Riel, which has been restored to its 1886 appearance. Through costumed interpreters and insightful exhibits, you'll get a personal look not just at the Riel family, but at the lives of the Métis hivernants (buffalo hunters) and the vibrant riverside community that Riel fought to protect.
Address:Â 330 River Rd
Cost:Â $4.50/$4.00/Free (Adult/Senior/Youth)
Hours: Summer season only
Final Thoughts
Two days is just enough to scratch the surface of Winnipeg, but it's more than enough to feel its pulse. This is a city that doesn't boast; it simply is. It's a place of quiet resilience, of profound history, and of a creative spirit that thrums just beneath the surface. My visits, especially my stop on the solo drive, have shown me that Winnipeg is a city of layers—Indigenous and settler, boom and bust. It's far more than just the 'middle' of the map; for me, it's become the true, complex, and enduring heart of the cross-Canada journey. It's a city that rewards curiosity, and I already can't wait to go back and peel back another layer.
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