Take a walk down memory lane and discover the past in this historic town. We welcome you to search for the many heritage plaques and markers on buildings of historical and architectural interest along Main Street, including:

Charles Hargrave Simpson Building, 184 Main St. S.

Ontario’s first woman druggist, Anne Mary Simpson, operated an apothecary here from 1886 to 1914. The building is c. 1850.

Wesley Block, 200 Main St. S.

Site of the North American Hotel, a coaching house where William Lyon Mackenzie made an important pre-rebellion speech in August 1837. In 1903 the Sovereign Bank building replaced the hotel.

Robert Simpson store, 226/228 Main St. S.

Robert Simpson opened his first business with partner William Trent on this corner in 1858. In 1871, he moved to Toronto, founding department store chain Robert Simpson Co.

King George Hotel, 232 Main St. S.

King George Hotel, circa 1845, was established by James Forsythe as the Forsythe House on the site of an earlier hotel owned by fur traders, Roe and Borland.

Cawthra House, 262 Main St. S.

Cawthra House, c. 1830, replaced John Cawthra’s trading post on this site. It was his home, store and Newmarket’s first bank (est. 1865). Danforth Roche’s general store was here from 1876 to 1923.

Dr. William G. Hutt home and practice, 145 Main St. S.

The first hospital in York County was opened here with six beds in 1922 by Drs. Lowell Dales and J.H. Wesley. It was the forerunner of York County Hospital (Southlake Regional Health Centre) and became a public institution in 1924.

Roadhouse And Rose, 157 Main St. S.

Roadhouse & Rose is Newmarket’s oldest business. Founder Samuel Roadhouse became a cabinetmaker apprentice with John Botsford in 1838. Five years later, he owned the business. In 1921, the firm took its present name.

William N. Starr building, 189 Main St. S.

Constructed 1863, the building has been a hardware, bakery, book, and stationery store, and an early telephone exchange in 1910. From 1919 to 1945, it was Theodore Bolton’s bakery. Elman Campbell followed with a stationary and china business here.

Caldwell Block, 205 Main St. S.

In 1864, Robert Simpson and partner M.W. Bogart moved their business here. Burned out in October 1870, the store reopened two months later. In June 1871, Simpson left to open a department store in Toronto.

William Roe fur trading post, 253-261 Main St. S.

William Roe became a fur trader at the ford on the Holland River in 1814. His first post was here. It eventually grew into a substantial home, a general store and a post office.