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William N. Starr Building
The William N. Starr Building, located at 189 Main Street, was constructed in 1863 and has been home to a variety of businesses throughout the years. A hardware store, a bakery, a stationary and book store, a telephone exchange and a china shop have all been housed in the building.
Address: 189 Main St. S. Newmarket ON
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Charles Hargrave Simpson Building
Located on the west side of Newmarket's historic Main Street, the Charles Hargrave Simpson Building was constructed in the middle of the 1800s and is notable because Anne Mary Simpson, the province's first woman druggist, operated an apothecary onsite from 1886 to 1914.
Address: 184 Main St. S Newmarket ON
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Caldwell Block
Robert Simpson's original store in Newmarket opened on the west side of Main Street in 1858. Simpson, along with partner M.W. Bogart, moved the shop to this site in 1864, before eventually heading to Toronto in 1871 to establish a department store chain.
Address: 205 Main St. S Newmarket ON
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Dr. William G. Hutt Home and Practice
Located in the east side of historic main street, the Dr. William G. Hutt Home and Practice is the site of the first six-bed hospital in York County. The hospital was opened by Drs. Lowell Dales and J.H. Wesley in 1922.
Address: 145 Main St. S. Newmarket ON
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Roadhouse and Rose
Located on the east side of historic main street and founded by cabinetmaker Samuel Roadhouse in 1843, Roadhouse & Rose is the oldest business in Newmarket.
Address: 157 Main St. S Newmarket ON
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Old Town Hall
Built in 1883, Newmarket's Old Town Hall gives visitors the chance to see architecture of the late 19th century. The hall is home to an amateur theatre group and a farmer's market takes place here each week. The Market Square across the street is another popular gathering spot.
Address: 460 Botsford St. Newmarket ON L3Y 1T1
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King George Hotel
The site on which the King George Hotel stands was originally the home of another hotel built by fur traders Roe & Borland. The current building was constructed in 1845 by a local named James Forsyth.
Address: 232 Main St. S Newmarket ON
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William Roe Fur Trading Post
William Roe, who was a fur trader at the ford of the Holland River in 1814, opened his first post on this site. Over the years the building grew to include a home, a general store and a post office.
Address: 253-261 Main St. S Newmarket ON
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Cawthra House
The original building at 262 Main St. S was a trading post run by John Cawthra. In 1830 a new building was constructed and this became Cawthra's home and store. The town's first bank was established here in 1865.
Address: 262 Main St. S Newmarket ON
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Robert Simpson Store
Robert Simpson, who eventually went on to found the Robert Simpson Co. department store chain in Toronto, opened his first business on this site in 1858 with partner William Trent.
Address: 226 Main St. S Newmarket ON
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