Beyond Borders: See you in Winnipeg!

This is the fourth and final installment of Beyond Borders, a series exploring how queer and trans employees navigate the evolving landscape of business travel. In previous editions, we examined the impact of political shifts in the United States and the challenges of corporate activism. Now, we turn to a city that exemplifies what it means to move beyond performance and into action: Winnipeg. Originally posted on LinkedIn.

For years, my birthday tradition was an escape to Palm Springs, where the August off-season meant quiet streets and endless sunshine. But with the Canadian dollar making U.S. travel less appealing this year, I set my sights closer to home. I’ll be celebrating in the Rockies with a trip to Banff, perfectly timed with Calgary Pride.

Before that, though, my Pride season always kicks off in the city that does it best: Winnipeg. No Canadian Pride blends community, history, and activism quite like the Pride Winnipeg Festival. If you’re looking for a Pride season destination where you’ll feel truly welcome (without stressing over exchange rates) Winnipeg is the place to be. Here’s why:

A Living History of Pride and Progress

The first time I attended Winnipeg Pride, it was for the unveiling of the design for Canada’s 2SLGBTQIA+ National Monument from Public City Architecture and frequent Pride at Work Canada collaborator Albert McLeod. The design, Thunderhead, reflects the resilience of our communities while honouring all that we have lost on the road to liberation. That year, I was introduced to the PRISM mentoring program at Big Brothers Big Sisters of Winnipeg by my friend and colleague Mackenzie Kolton, a groundbreaking initiative matching 2SLGBTQIA+ youth with mentors who share their identities.

The following year, my colleagues Matthew Cutler and Noreen Mian introduced me to Place of Pride, the centerpiece of Rainbow Resource Centre’s capital campaign and Canada’s first 2SLGBTQIA+ housing and support campus for elders. While other cities debate how to support an aging population, Winnipeg’s community is leading the way and building real solutions.

Last year, I arrived early to attend the annual vigil honoring those the community has lost. I was lucky enough to hear stories of Dr. Dick Smith, a pioneering physician who established Manitoba’s first queer-focused medical clinic during the HIV and AIDS crisis. His legacy was honoured by his colleagues from Our Own Health Centre, who reminded us that Dr. Smith’s story is a reminder of how one person’s courage can change countless lives.

At that vigil, I also met Winnipeg’s chapter of Dykes on Bikes, who fundraise for 2SLGBTQIA+ causes through their annual (and family-friendly!) Bikers and Babes calendar. As the son of a Honda rider, I, of course, bought fifty. And I’m eagerly awaiting the 2025/26 edition so I can buy fifty more.

Community-Led Safety and Innovation

This summer marks my fourth year in a row visiting Manitoba. And every year, the province gives me another reason to come back. While Saskatchewan and North Dakota pass anti-trans policies, Manitoba moves forward. The province’s Deputy Premier is nonbinary (and thankfully a huge supporter of Pride at Work Canada).

Winnipeg is a city of helpers, constantly finding ways to make life better for its residents. The Downtown Community Safety Partnership (DCSP) Winnipeg is a perfect example. The program provides 24/7 support to make downtown Winnipeg safer for all, with teams trained in overdose response and de-escalation. Their impact was clear from day one at Portage Place, where the DCSP’s very first shift involved saving someone’s life using naloxone.

On May 28, 2025, Pride at Work Canada / Fierté au travail Canada will present ProPride Winnipeg: Living History at the Canadian Museum for Human Rights. This event will highlight the Love in a Dangerous Time exhibit, which documents the story of the LGBT Purge Fund | Le Fonds Purge LGBT and will bring together voices from today’s human rights struggles.

The Best Pride Festival in Canada

The Pride Winnipeg Festival stands out as one of the most community-driven Pride festivals in the country, making it the perfect fit for me. The parade is a full-family event where parents cheer on their kids, chosen families march together, and programming is intentionally designed to welcome a range of ages and audiences throughout the weekend.

Every year, the most powerful moment for me is the Trans March, where the future is being shaped in real time. Last year, at the rally on the steps of The Ledge (the Manitoba Legislative Building), longtime activists stood alongside young trans kids from rural Manitoba, sharing what it was like growing up outside the city.

The Celebrations Never Stop

Winnipeg Pride delivers when it comes to celebration. Cocktails Off Broadway, which has a fascinating history, offers a sophisticated night out, while the Little Brown Jug Brewing Company hosts a street party that never disappoints. The Saturday before the parade features Saturday Night Pride, a fundraiser for Rainbow Resource Centre. And of course, no visit to Winnipeg would be complete without a stop at Club 200, home to the legendary Lesbian Lube Wrestling Championship. It’s exactly what it sounds like, and not to be missed.

Why Winnipeg Matters

For years, people have called out the performativity of Pride. And in a shifting political climate, I expect we’ll see fewer corporate floats and less rainbow merch this year. Not because they’re being replaced with something better, but because the willingness to stand by our communities, through thick and thin, is fading.

But that doesn’t mean Pride itself has to fade. Where we choose to put our energy and our investment matters. In Manitoba, queer and trans communities aren’t waiting for permission or support to get things done. They’re actively building institutions, networks, and spaces that will endure, no matter what. There’s a lot the rest of Canada can learn from them. And if we want more cities to follow Winnipeg’s lead, we need to show them it’s worth it.

With Rendez-vous Canada happening the same week, hotels are already filling up. So, book your trip, get involved, and experience a Pride that’s rooted in connection and action.

Need introductions? I know a few people who’d be happy to meet you.

See you in Winnipeg!