From the halls of Massey High School to some of the most remote corners of the world, past student Tom Hudson has certainly taken the road – and waterways – less travelled.

Tom attended Massey High School from 1996 to 1997 and has since developed a passion for adventure that has taken him on some incredible journeys around the world.

The Canadian Canoe Journey

Most recently, Tom completed an extraordinary solo canoe journey across Canada, paddling from Saskatchewan River Crossing in the Rocky Mountains all the way to Old Montreal in Quebec.

The journey lasted an incredible 216 days, concluding in August 2026. Perhaps even more remarkable is that Tom began the expedition with no previous canoeing experience. After selling his house and closing his construction business, he decided it was time for a change and set out on a new adventure.

The journey certainly did not come without its challenges. On just his fourth day, Tom capsized and lost his gear. Fortunately, a local man and his family came to his aid.

There were also some very special moments along the way. While travelling through Manitoba, Tom came across Ivy, a lost 14-year-old dog stuck in the mud. He rescued her and was later able to reunite her with her owner.

Tom’s remarkable journey also attracted attention across Canada, with his adventure featured by major Canadian media outlets, including CTV News and CBC News.

But completing a 216-day journey across Canada has not slowed him down.

What Comes Next?

Tom is an experienced sailor and spends much of the year exploring the world by sea. From September through to April, he plans to continue sailing around the world, documenting his experiences and sharing the highs, challenges and incredible places he encounters.

And there are already plenty more adventures on the horizon.

Tom is currently considering several ambitious expeditions for his next challenge, including canoeing across Europe, travelling across Mongolia on horseback, or canoeing from Canada through the United States to Mexico. He plans to take on one of these adventures next year.

Tom shares his journeys through his YouTube channel, What in the World (@WhatInTheWorld_Tom), documenting his sailing adventures and the incredible places he visits along the way.

It is always fantastic to hear where life has taken our former students, and Tom’s story is certainly a unique one.

We wish Tom all the best as he continues his journey around the world and look forward to seeing where his next adventure takes him.

Follow Tom’s adventures – What in the World: