Rail service to Owen Sound began in 1873 and included grain elevators, freight sheds and a roundhouse, the foundations of which can still be seen at 13th Street. This modern station was built in 1946, part of a pilot program to modernize CPR facilities after World War II.  Passenger service ended in 1970, freight service in the mid-1990s. Vacant for many years, the City purchased the Station in 2010 and restoration is underway.

Built circa 1897 near the Canadian Pacific Railway yard, the Station Hotel served as a boarding house, hotel and as overflow waiting area. There was also a restaurant that served patrons from the main floor.

Owen Sound has been home to a Jewish population for as long as there has been a town here. Regular services were held by 1904, first in homes, then in rented sites. In 1947, this Calvary Church was purchased and named in honour of Isaac Ezekiel Cadesky, a driving force in the establishment of the present synagogue.

This intersection has been dubbed "Salvation Corners" because of the four remarkable limestone churches that anchor this spot, just one block east of "Damnation Corners".

The Church of Christ Disciples was formed in 1842 and they built this church in 1889 in the style of an early English country church. In 1957 the Church of the Nazarene bought the building.

The Anglican congregation was established in Owen Sound in 1846. This church was built in 1881, patterned after St. Mary's Church in Bristol, England. The parish hall was built in 1898. An addition was built in 1968. A complete restoration of the steeple was undertaken in 2010-2011.

Owen Sound's first Baptist congregation was established in 1853. Their first building on this site was erected in 1879.  This stone church was built in 1903. 

The first church on this site, called Division Street Presbyterian, was erected in 1857. The current church was built in 1886. The congregation joined the United Church of Canada in 1925. In 2012, Division Street United merged with Knox United to become Georgian Shores United.

Dr. John A. Hershey built this house in 1899 for his family and his medical practice, and patients would enter through the 4th Ave East door. Dr. Hershey would also teach medical students at his practice, including the famous Dr. Norman Bethune. When Dr. Hershey died unexpectedly in 1921, his practice was taken over by Dr. George Robert Miller, who practiced until 1932. The building is now used as MacLean Estate Bed and Breakfast, with rooms named after each doctor.

Knox Presbyterian formed in 1846. This structure was built in 1873 and enlarged in 1886. With Congregationalist Union, it became a United Church in 1925. In 2012, Knox United merged with Division Street United to become Georgian Shores United Church (see #8). The building is now home to Harmony Centre Owen Sound, whose motto is "preserving this place for our community to share, create, and perform".

Built in the early 1870s, this home was used as a manse for Knox Presbyterian Church around 1900, and is now apartments. Originally Georgian in style, with simple design elements, two additions added the large tower, bay windows, and hipped roof.

Real estate and insurance agent William R. McColl owned this house in the early part of the 20th century. This house, along with several others in the neighbourhood, has an interesting double-gable gambrel roof which is a sign of a common builder.

In 1868, Boyd St School was built at a cost of $1,905. The playground across the street was home to curling and skating rinks from 1888 to 1929. The school was enlarged several times, and in 1910 it was renamed Ryerson School. In 1990, it was converted into a 36-unit apartment building.

Robert and Estelle Wright had this house built in 1923 by local contractor Telford & King. Wright was a pattern maker at the Owen Sound Iron Works, and later a foreman at Wm. Kennedy & Sons. An example of the Craftsman Style of architecture.

Frederick Nicholas D'Orr LePan opened a general store in Owen Sound in 1848. Born in Ireland, LePan was a liquor and wine merchant who also sold groceries and other provisions. This Regency Cottage was built about 1865 by LePan. (See Downtown Tour #18)

Built in the late 1850s, this Georgian style home was used for church services until 1874 (traces of the entry door can still be seen on the north façade), then as a private school, a grammar school and a boarding house. Sold to the Rixons in 1888, it stayed in the family until 1973.

This Queen Anne Revival style house was built in 1891 for David and Martha Butchart, influential in the development of the Portland cement industry in Canada. David's brother, Robert P. Butchart and his wife Jenny, moved to British Columbia in 1902, forming the Vancouver Portland Cement Co. In 1921 Robert closed his quarry and Jenny developed the famed Butchart Gardens.

Built in the late 1800s, this collection of three row housing groups shows mixture of styles, including Gothic Revival and Italianate, with a variety of architectural elements, such as gables, gingerbread trim and bay windows.

The County of Grey Registry Office was built in 1855 by contractor John Frost, who later became Mayor of Owen Sound.  In 1923, an addition was constructed and in 1961, the building was used as municipal offices during construction of the new City Hall.

Originally built in 1874 as a Regency cottage with verandahs facing both 3rd Avenue East and the harbor, it was transformed into this East Coast Queen Anne Revival style in 1885 by Jim and Annie Maitland. Jim was in the lumber business and Annie was a granddaughter of Richard Carney, the first mayor of Owen Sound.

The Grey County Jail was built in 1853, a requirement for the new County's formation the next year. A total of three hangings took place in the Jail, the first on December 5, 1884; a 55-year-old blind man named "Cook Teets" was convicted of poisoning his wife, though later her mother confessed to the crime.

Built in 1853, this example of Canada West Classical Revival is constructed of rubble stone with golden quarried limestone overlaying the front façade. The large two-storey tower is a later addition, made to the south end in 1885.

In 1850, the Village of Sydenham appointed 30 volunteers and purchased fire fighting equipment. In 1891, a new fleet of horse drawn equipment was acquired for the Fire Hall located next to the Town Hall (See Downtown Tour, #2). A by-law was passed in 1907 to hire 14 full time firefighters; in 1917, the number was increased to 28.