A Few Stories and Plenty of Questions

“Maybe because I was young and foolish. No, I wasn’t young. I was 50.”

That was Henry Gold’s explanation when asked why he thought he could take a group of cyclists across Africa. His cycling experience at the time? Mostly commuting around Toronto.

On November 4, Henry joined Shanny Hill, Miles MacDonald and Michael Coo for a live info session. With TDA’s 25th anniversary approaching next year, we asked our founder to revisit the early days, including a support vehicle stuck at customs just before the first tour. Getting everyone to the starting line was already an adventure.

The conversation soon moved to how one African expedition became a company running tours around the world. Henry also admitted that he wasn’t immediately convinced by every idea. Cycling in India? He had questions. Then he went, and found himself reconsidering everything he thought he knew about the place.

That curiosity still shapes what we do. As Henry put it: “It’s not a scripted adventure.”

Miles introduced our 2027-28 tours and explained the different tour styles, while Michael covered registration and preparing for your first trip. Your questions took us behind the scenes of route planning, scouting and the friendships that bring riders back year after year. We also discussed cold drinking water, because even a conversation about crossing continents needs to address the essentials.

Thank you to everyone who joined us and kept the questions coming. If you missed the session, the full recording is available below.