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The building located at 15 Holland St. East was bought by Harold Boyd many years ago. He ran a pool room on the ground floor on the west side. He added a second floor above the pool room for living quarters. Jack Pong owned a restaurant on the east side of the building in the 1930’s. (1, 2)
The two-storey, brick and cement building located at 19 Holland St. East was owned at one time by George Simpkins. He ran a plumbing, heating, electrical, and eavestroughing company upstairs. There was a show room downstairs and the east side was a workshop. George and his family lived on Moore St. across from Joseph Street. Ethel Gapp was his bookkeeper, Ted Gapp was his electrician, and George Manton did the heating work. They drove for miles around the country in a Model T truck. Harry Barron bought the business in the 1930’s and kept the same workmen. Then the business was moved to the southwest corner of Holland and Simcoe Streets. (1, 2)

The Village Inn is located at 2 Holland St. East (on the corner of Holland and Simcoe Streets). There had been a hotel located at this site before the great fire of 1871. The building in this photo (1995) was built in 1920 in the Ontario Vernacular style. The original two-storey, cement building contained living quarters upstairs. One of the early inhabitants was Dave Watson, a farmer from the Scotch Settlement. He was one of the first to work with Professor Day in bringing about the drainage of the Holland Marsh. The ground floor was a grocery store in the early 1930’s (or before it was bought by Jim Gray and his wife). It was separated by a central entrance downstairs.
Ken Morris bought the building around 1933 or 1934. Renovations were done by Art and Len Saint in 1937. The building was converted into the English Tudor-style hotel currently known as “The Village Inn”. A one-storey addition was added later (on the east side of the building) to contain a restaurant and ladies’ room. Under Jack Pong’s ownership, the addition became a Chinese restaurant. Additions were built later at the rear. Frank Sakowski ran the Inn for a while before it was sold to Bill Callum and Mr. Grant.
The two-storey building has a wide, rectangular plan with an asymmetrical organization and a typical ‘Main Street’, storefront façade located at the street line. It is characterized by a high, flat, ‘boomtown’ façade and cornice with brick dentils. The prominent, corner entrance door is oriented diagonally toward the street intersection. Existing door and storefronts are not original. The upper-floor pairs of windows suggest some original Italianate styling. The windows are not original on either level. At the time of the 2000 inventory, the building had masonry construction, stucco and wood siding, and a built-up, tar and gravel roof. It notes that the modest, commercial building is in fair condition with no original details visible. (1, 2, 3)

The buildings shown in this photo are located at 21, 23, 25 and 27 Holland St. East. One of the buildings in this row was once a bakery and confectionary owned by Jack Madil. There were two ovens in the rear and a barn at the back of the property. Jack later sold the business to Fred Gowland in the early 1930’s and bought a farm (on the north side of Concession 10, on the west side of Sideroad 10). Fred and his family moved into the living quarters above the bakery. He had a partner and second baker named Bert Hunt. Fred later got a job as head baker at the Penetanguishene Asylum and moved to that area. Bert was left to run the business until he got sick. The business was then closed and the building was sold.
The 25 Holland St. East address was the Liberal Party office for Kraft Sloan in 1995.
The 27 Holland St. East address was the location of a barber shop run by Joe Scotto for over thirty years. (1, 2)

The building located at 31 and 33 Holland St. East once housed an implement business run by Frank Allan and his son George. Leonard Saint and Sinclair MacDonald cemented the building and flattened the roof. There were four rental apartments upstairs. In the front there was a large plate glass window, a door, a smaller plate glass window, and another door for bringing in machinery. There was also a counter and parts department. The workshop in the rear had a small and a large rear door. (1, 2)

The two-storey, frame building located at 36 Holland St. East was clad in cement in 1927 by Len Saint. Miss Sarah McDonnell, accompanied by her sister, ran a boarding house here.
The frame building located at 38 and 40 Holland St. East was bought many years ago by Mr. McWilliams. He remodeled the structure and put the entrance for the upstairs apartment on the east side (42 Holland St. E.). He died many years ago and Mrs. Mary McWilliams (a sister of William Hirlehey) and her son Bill lived in the apartment. Bill worked on the marsh and in a hockey stick factory. There were two shops downstairs. There was a shoemaker and leather shop for years at 38 Holland St. East (on the west side of the building). There have been several other businesses here including Joyce’s Curio Shoppe (as seen in this photo taken in 1995). (1, 2)

The frame building located at 38 and 40 Holland St. East was bought many years ago by Mr. McWilliams. He remodeled the structure and put the entrance for the upstairs apartment on the east side (42 Holland St. E.). He died many years ago and Mrs. McWilliams (a sister of William Hirlehey) and her son Bill lived in the apartment. Bill worked on the marsh and in a hockey stick factory. There were two shops downstairs. Joe Scotto barbered at 40 Holland St. East (on the east side of the building) for a number of years before moving across the street to “Rusty” Worfolk’s property at 27 Holland St. East. There was a shoemaker and leather shop for years at 38 Holland St. East (on the west side of the building). There have been several other businesses here including Joyce’s Curio Shoppe (as seen in this photo taken in 1995). (1, 2)

The Edmund Garrett House is a two-storey building located at 45 Holland St. East. It was built in the Classic Revival style in the 1880’s (after the fire of 1871 that destroyed much of Bradford’s downtown). The building was converted into two living quarters many years ago and was once the home of the VanZants (on the west side) and the Bennett family (on the east side). George Bennett, a powerful man and labourer, dug (by hand) a large number of the ditches on Dufferin Street. Howard Thornton eventually bought the building and started a crate factory with Bill Fuller in the barns at the rear. He had a crate and lumber yard on Back Street. Howard and his brother also owned Barron’s Hardware store. After Howard died, Mrs. Thornton rented the upstairs apartment and lived downstairs by herself. After her death, the town bought the structure and had it remodeled to accommodate the Bradford Police Station on the ground floor, which it housed from 1980-2008, and the building inspectors’ office on the upper floor.

The building has a modified, rectangular ‘temple’ plan with a projecting frontispiece flanked by two-storey wings on either side. A medium-pitched, gable roof has a plain cornice and frieze supported on small brackets. There is an enclosed, raised porch with a shed roof and a plain cornice and frieze supported on small brackets. The building has tall, narrow window openings with high floor to ceiling heights. Windows are used to highlight the frontispiece with an angular, flat-roofed bay at the ground level and a projecting cornice and eaves on brackets. Double, semi-circular, arched windows at the second floor are highlighted with dichromatic, brick voussoirs. There is a rose window set within the gable into a round opening of cut-stone voussoirs. Other windows are set into rectangular openings with stone (or concrete) lintels and lug sills. The original windows were probably multi-paned and double-hung. Masonry construction has brick cladding and there is a coursed, rubble-stone foundation. The two, two-storey additions have filled in the east corners of the building and the entrance porch has been modified and enclosed. According to the 2000 inventory, the structure is in good condition with some original details remaining. (1, 2, 3)

The building located at 5 Holland St. East (near the northeast corner of Holland and Barrie Streets) has solid-brick construction. The office of veterinarian Dr. Stephenson (who lived on Queen Street across from the public school) was on the ground floor at this address. Grain buyers worked upstairs. They had their own stairway and a huge, walk-in safe. Later, that space was turned into an apartment that became the home of Rae Green after WWII. Around 1928 or 1930, Fred Buck (a pharmacist) opened a drugstore on the ground floor. It later became Brackens Drugstore and was run by Mr. Harrison. (1, 2)
The building located at 9 Holland St. East (beside 5 Holland St. East) also has solid-brick construction. It was the site of Dennis Nolan and Jim’s Model T Ford dealership. There was a garage with an elevator. Overhauling was done in the basement and painting was done upstairs. Hugh Bannerman pumped gas and Rose MacEwan was the bookkeeper. Nolan had as many as 10 employees working for him at one time. Mr. Martin moved in around WWII and opened a used furniture and appliance store here. It was later sold to Bob Sewery, a WWI veteran. (1, 2)

The two-storey, frame building in this photo (from 1995) was once located at 52 Holland St. East. It and sat on a narrow lot and had long sheds at the back. Several families lived here over the years, including Joe Graham, his wife, and sons Leonard, Ogil, Weldon, Gilford, Leeson and Donald. Joe was a semi-retired farmer from the Cookstown area and he ran a farm on Concession 6 on the south side (west of Simcoe Road). The boys had a butcher shop and Weldon trucked, hauling coal for the dredge on the big canal and fill for the dam from Simcoe Street. Harold Boyd eventually bought the property. He had Sinclair MacDonald remodel the structure and add a rental apartment upstairs. Harold’s daughter and her family lived in the rental apartment before the building was demolished in the 1990’s. A plaza was later built on this (and the adjoining McLain) property. (1, 2)

The two-storey frame building located at 93 and 95 Holland St. East was originally a dry hotel and a boarding house. It was later divided into two separate living quarters. Henry Pringle and his family lived on the west side (93 Holland St. E.) for a number of years before moving to the north side of John Street. Tom Fuller and his sons Leonard and George lived on the east side (95 Holland St. E.) for years before moving to John St. (on the northwest corner of Colborne Street) to a house built by Dan Collings. (1, 2)