In 1849 a young Thomas Holliday left his home in Beeford, Yorkshire, England to travel to pre-confederation Canada. He located in Toronto where he learned the butchering trade before moving on to Stratford in the early 1860s and finding work with William Worth, a hotel keeper who built the Worth Block on Wellington Street just to the west of the Easson Block.

The hotel business, which was flourishing in those early Stratford days, caught Thomas' attention. Travellers could now access the railway services provided by the Buffalo and Lake Huron Line and the Grand Trunk Railway which were both then established in Stratford. In 1867 he opened the Corn Exchange Hotel in a small frame building adjacent to the east side of the Easson Block on Wellington Street. He subsequently engaged a prominent local architect, Alexander Hepburn, to design a much larger and more well-appointed facility on the property which he named the Royal Hotel. For many years the Royal, with its prominent site on Wellington Street, was known as one of early Stratford's finer hotels. It was destroyed by fire in 1964. Currently Rene's Bistro, Wuerth's Shoes and Sinclair Pharmacy are located where it once stood. 

Thomas married Mary Ann Guy, also of English heritage, who was born in Whitby just east of Toronto. Their first son, Thomas Jr., was born in 1871. In 1870 Thomas rented the hotel and purchased a 100 acre farm property, Lot 7, Concession 1 (4275 Huron Street), in the former Downie Township, now Perth South, land which had been previously owned by his colleague William Worth. Shortly after his purchase an old log house on the property was destroyed by fire. Thomas replaced it later in 1870 with the present fine brick structure which became the Holliday home where he and Mary Ann raised their family of four sons and six daughters. They named the property Woodview Farm and today the house which faces onto Highway 8 is part of the Stratford Perth Museum.

As well as his hotel and farming responsibilities, Thomas was involved in early Stratford businesses such as the Stratford Gas Company, the Waterworks Commission and the Dam Syndicate. His eldest son, Thomas Jr., became the owner of the Stratford Bridge and Iron Works which he developed into a highly successful manufacturing company doing business across the country. His father was a key adviser.

In 1907 Thomas and Mary Ann returned to Stratford to live at 113 William Street, the former residence of William Easson, and after a few years sold the farm to their second son Edward. Thomas died in May 1914 just as the First World War was about to begin. Mary Ann passed away at age 64 in1917. Both are buried in Stratford's Avondale Cemetery together with several family members.