Like so many Yukoners, Gregory was born in a big city but was drawn to the North. A native Torontonian, he first developed a love of the outdoors on family camping and canoe trips as a child, and at summer camps. After his own father’s premature death, Gregory spent his early twenties seeking adventure. He travelled throughout North America, hitchhiking and sleeping in the homes of people both known and unknown.

After reading a news story about an international cyclist, he was inspired to bike solo from Toronto to Yellowknife in 1970. Energized by cheap candy bars and oatmeal, and often benefitting from the hospitality of locals who were intrigued by his journey, he managed to spend a measly $4 a day. He returned the favour many times over by inviting travellers to stay at his home in Whitehorse.

He began his biggest adventure in 1974 when he was hired as a staff member at the Carcross Community Education Centre. It was in this period of his life that he made lifelong friendships, met his first wife, Lorraine Young, and explored the expansive landscapes, river valleys, and mountain peaks of the Yukon.

After he and Lorraine married, they moved to Old Crow in 1977 where they managed the local co-op store. They eventually settled in Whitehorse in 1979 and had three children, Sarah, Ben, and Lizz. After Lorraine’s death in 1988, Gregory married his second wife, Sandy, and helped raise her four children, Matt, Josh, Amy and Sarah, as his own.

Gregory worked for YTG for 33 years, mainly as an accountant for Health and Social Services, retiring in 2014. He also ran a bed and breakfast for the final 18 years of his life. He took great pride in this part of life, even directing his kids to look up a recent online review to share at his funeral. The reviewer described Greg as "a fount of sensible local knowledge" and praised Greg's dedication to ensuring his guests experienced the Yukon that he loved so much.

He was a keen writer throughout his life, never missing an opportunity to write a strongly worded letter. He built a community of long-time friends around the globe on an online dictionary forum, and in recent years, he wrote a monthly column for the Whitehorse Star about language.

Gregory was an active volunteer throughout his life, most recently with the Co-ed Recreational Soccer League, where he served on the executive for 17 years, and the alumni group of the Carcross Community Education Centre. He loved to sing and was active in the Whitehorse Community Choir.

He will be remembered by his children as a father who would drive home to make tomato soup and tuna sandwiches during the school lunch hour, who would always respond to requests for help, and who loved nothing more than hopping in the car for a drive somewhere – maybe just down the highway to the Carcross desert to run around, or maybe all the way to Ontario with a pile of kids in the car.