Jay Underwood is a graduate of the journalism program of Holland College of Applied Arts and Technology in Charlottetown, Prince Edward Island. Jay began his career in newspapers as a nightshift proof reader and obituary writer with the Charlottetown Guardian-Patriot. He then moved to the New Glasgow, Nova Scotia Evening News, as a reporter-photographer, and to the Truro, Nova Scotia Daily News as city editor. Briefly serving as city editor at the Timmins, Ontario Daily Press, he returned to Nova Scotia as editor and publisher of the Springhill-Parrsboro Record, and the Enfield Weekly Press, before joining the staff of the Halifax Daily News as senior copy editor and a member of the editorial board. Disabled by complications of diabetes that took most of his sight in 1999, Jay focused on his love of history and railways, producing Ketchum's Folly in 1995, and Full Steam Ahead: The life and locomotives of Alexander Mitchell in 1996 (Lancelot Press), and, more recently, Built for War: Canada's Intercolonial Railway' (Railfare*DC Books) in 2005. Now in his third term as president of the Nova Scotia Railway Heritage Society, Jay and his colleagues were successful in preventing the historic 1905 vice-regal railway car Alexandra from being scrapped, and the car is now being relocated to a museum site at Tatamagouche, Nova Scotia for restoration and public display. The society is planning to celebrate the 150th anniversary of the opening of main line railway operations in Nova Scotia in 2008, which will include the railway built by James Richardson Forman. He is a frequent contributor to Canadian Rail, the journal of the Canadian Railroad Historical Association, and has plans for other books in the near future.

His work centres on topics not previously covered by conventional history texts. Jay lives in Elmsdale, Nova Scotia with his wife Kathy and son Derek. His oldest son, Andrew, is pursuing a career as a railway freight conductor with Canadian Pacific Railway.