The First Trans Person to Cycle Around the World

After 337 days, 20 hours, and 17 minutes, riding over 29,000 kilometers, Robbie Danger Webb set a new Guinness World Record as the first openly transgender person to circumnavigate the globe by bicycle. Find a stirring written reflection from Robbie with photos from their massive achievement here…

Finish photos by Sunny Gajadhar

It’s a Saturday afternoon in the leafy suburbs of Mount Albert. Both of my housemates are out at work, so I’m recording a video.

“About a month from now, I’m—ah fuck.” Start again.

“Hey, it’s Robbie. I’m 29 years old. My pronouns are they/them. About a month from now, I’m leaving my home in Aotearoa, New Zealand. I’m aiming to be the first transgender person to cycle around the world.”

robbie Webb trans around the world record
  • robbie Webb trans around the world record
  • robbie Webb trans around the world record
  • robbie Webb trans around the world record

I’m a nerd for other people’s world rides. I’d been planning my own for over half a decade. I’d followed the likes of Ed Pratt, Mark Beaumont, and Jenny Graham. On a whim, I checked to see if there were any world cycling records available for someone like me.

There it was. “First openly transgender person to circumnavigate the globe by bicycle.” I didn’t have to pitch the idea–the record was up for grabs. Cycle at least 29,000 kilometres in an east or west direction. Collect two antipodal points, gather mountains of evidence, and never stop for more than two weeks, or you’re out.

  • robbie Webb trans around the world record
  • robbie Webb trans around the world record

At my planned speed, there’s a three-month window every year to leave for the ride. That would help me avoid the coldest snow and the hottest sun. It seemed like 2024 had to be my year. The US presidential campaign is, as usual, transphobic. The UCI is pushing transgender cyclists out. Anti-LGBTQIA+ conservatism is rising in eastern Europe. And most of all, home’s not hitting the way it used to. It feels lonely down in the bottom of the world.

With 32 kilograms of steel gravel bike and gear, off I went to Auckland Airport. Thirteen hours of flying to Vancouver, then I’d proceed east. From British Columbia, I’d head down into the United States on the Tour Divide route. Back up to Montreal, then flying to Lisbon, riding up to Glasgow, across to Berlin, and southeast to Tbilisi. By then, the winter snow would be nipping at my heels. I’d cross India, then fly from Kolkata to Perth to cross Australia.

  • robbie Webb trans around the world record
  • robbie Webb trans around the world record
robbie Webb trans around the world record

The final leg would take me from Invercargill to Auckland. That last leg in New Zealand, I didn’t need to look at my bike computer. I know Ngā Haerenga (the New Zealand national cycle trail) like the back of my hand.

Bicycle destruction followed me everywhere I went. A car accident in the USA that destroyed my fork and gave me five stitches around my right eye. A tyre that shredded all the way through across the Nullarbor Plain. Cranks that sheared off and had to be zip-tied back together. A wheel swap at HUNT’s warehouse in Dresden. Three tents, three sets of brake levers, three power banks, a phone, a camera, five pairs of tyres and 10 chains. An unsupported world record is tough! Not because of the pedaling but because of the sheer admin of it all.

Life on the bike is about chasing the next problem. Where to sleep. Where to eat. How to communicate without English. How to get what I need to fix my bike. What route? Post photos. Contact possible hosts on warmshowers and Instagram. Stay safe. Be a good and upstanding representation of your community and repeat… for more than 300 days.

  • robbie Webb trans around the world record
  • robbie Webb trans around the world record
  • robbie Webb trans around the world record
  • robbie Webb trans around the world record
  • robbie Webb trans around the world record

I loved it. I fell into friendships fast, passing what would usually take months, in a matter of hours. I got good at saying goodbye to those same friends, knowing we’d mostly be internet buds for the rest of eternity. I took up every person who’d ever offered “come stay with me in my country sometime.” I lost time on my record to hanging out and making friends, and it was worth every minute. After all, when you’re trying to be first, you don’t always have to be fast.

robbie Webb trans around the world record

When a transgender person does a big public project, people often frame the story around our suffering and perseverance. While there was plenty of that, too, I didn’t choose a world bike record for that reason. I did it because I love riding my bike, and making friends, and “why not do that but bigger” seemed like a pretty fun idea.

When I look back on it, I could count on one hand the number of times people were transphobic to me. Some of this is my privilege as a white New Zealander, who is trans-masculine, for sure. When I explained the record, most people responded with confused happiness or indifference. No problem. We wanna know what your favourite country is. How’d you figure out where to sleep? How do you do it on a budget (sleeping in a ditch and dumpster diving, of course), and how’d you get the bicycle over the sea?

  • robbie Webb trans around the world record
  • robbie Webb trans around the world record
  • robbie Webb trans around the world record
robbie Webb trans around the world record

It’s another Saturday afternoon. I’m running five minutes late. My panniers are full of wet clothes. It rained hard in the mountains the night before. I ran the clock down when I stopped to buy a pie at my favourite bakery. I stopped to pick up lost gear on the trail, and to chat to a cycle tourist. I wrote a quick Instagram story. “Last call for the party bus!” The party bus is big. All the hometown friends are waiting at the start of the bike path. They’ve got the trans flag ready, cameras, and Matt’s got a magnificent “Welcome home Robbie!” sign.

“Let’s go!” I say, aware that I’m running late to meet my witnesses, and pop up a curb. My Brooks tensioning bolt shears out, leaving me with less of a saddle and more of a flappy leather flap. I guess we’re pedaling standing up for the last five kilometres. My saddle exploded, but everyone else thinks it’s a sprint finish.

  • robbie Webb trans around the world record
  • robbie Webb trans around the world record
robbie Webb trans around the world record

Almost a whole year on from my start, and Auckland International Airport has changed. We’re lost in the car park for another 10 minutes looking for the international terminal. We make it eventually.

Over 8,000 hours of pedaling later, through 22 countries, and we’re done. First openly transgender person to ride a bicycle around the world. And by default, the fastest known time for a non-binary or transgender person, too. My friends all bought bottles of champagne to spray me with at the front door to the airport. One cop gets called. Good old New Zealand.

  • robbie Webb trans around the world record
  • robbie Webb trans around the world record
  • robbie Webb trans around the world record
  • robbie Webb trans around the world record

I’m not sure how long it will be before another trans person finishes this trip. In terms of world geopolitics, doors slammed behind me everywhere I went. Governments around the world have warned us not to travel to the United States. The day before I arrived in the Republic of Georgia, a new anti-LGBTQ law came into effect. Similar laws have now arrived in Hungary, Bulgaria, and Romania. The United Kingdom just made a ruling excluding transgender people from using public spaces as the gender they identify as.

But regardless of the world, we have always been here, and we always will be.

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