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The structure located at 38 Holland St. West (on the southwest corner of Holland and Drury Streets) was built around 1900 in the Ontario Vernacular style. B.B. “Ben” Collings lived upstairs with his wife (a Waldruff), and children Bernice, Kathleen and Norman. Both daughters became school teachers and Norman (“Dodger”) was a professional hockey player who helped his father and later took over the business. Ben’s workshop was also located here and there was a horse stable at the rear of the property many years ago. The back end of the building was destroyed by fire in the 1920’s. Ben Collings was involved in several businesses. He was also known as an organizer and sports manager. At one time this building was the site of the Collings’ mattress factory. Ben also cut marsh hay and hauled it down the river on a scow. Sometimes the hay was stacked for winter baling. The horses wore four wooden boots and wouldn’t get off the scow until they were applied. Ben was a furniture maker and an undertaker. His first experience as an undertaker was with the body of his own father. He bought Jack Spence’s fishing business (including nets, reels, pulleys, ropes and the fish shanty at the mouth of the river on the east side opposite the 8th Line). His largest catch of fish was five tons of carp. He fished in the spring and fall and put nets under the ice in winter. Carp was caught (when in season) and had to be kept alive for the Jewish market. He employed about eight men all year round. Later he had old cars cut down to make tractors. Ben and another man broke (worked?) Col. Bar’s marsh land at the north end of Federal Farms Rd. (Bathurst Street). The Newmarket Canal started and died on this property.
The two-storey, commercial ‘row’ building has second floor offices (or living space), a wide, rectangular plan with symmetrical organization, and a flat, built-up, tar and gravel roof. The ‘Main Street’ frontage with a typical, storefront façade is located at the street line. The Drury Street façade on the north portion of the building (fronting Holland Street) has a more informal façade with openings placed as required to suit the building’s requirements. The Drury Street building has a plain, symmetrical façade and is dominated by a wide, segmented, arch entrance raised slightly above the sidewalk. A loading door to the rear portion of the Holland Street building has a segmented, arch opening and a concrete sill raised above street level. The existing doors and windows are not original. There are several window openings with segmented, arch openings and concrete lug sills. Several basement windows (all topped with segmented arches) have been fully, or partially, blocked in. This suggests that the building was built before the existing road or town services were installed. The building has masonry construction, brick cladding, and a parged, stone foundation. According to the 2000 inventory, this modest, commercial building is in good condition with some original details. (1, 2, 3)

The Dr. Clement House is located at 41 Simcoe Road (on the southeast corner of Simcoe Road and Centre Street). It was built around 1830-1860 (1840’s?) in the Classic Revival style. Dr. Clement lived and died here after practising in the 1870-80’s. He was buried in Clement Cemetery on the 2nd Line in Innisfil (east of Highway 11). His wife Rachel lived here until her death. The house was then rented to Walton, a railroad man for the C.N.R. The barn and garden behind the building ran to William St. (as did all the properties on the east side). Sam Catania and his wife Sarah lived here in later years. They converted the house into two apartments and had a dry cleaning business in the garage that was eventually destroyed by fire. Sam sold the house to Bruce and Barbara Verney. They were still living here when this photo was taken in 1995. Bruce was a chiropractor. A building used as a dry cleaner was constructed later on the property. Jack Pong (a restaurant owner on Holland St.) built a house on the back of this property that extended to Centre Street.
The street level has apparently been raised considerably around this house as the current 1½-storey, two-bay house was originally 2½ storeys. It has an asymmetrical façade and entrance, a simplified ‘temple’ form, and a medium-pitched, gable roof. The pediment roof shape has return eaves facing the front. A hip roof on the raised entrance portico is supported on wood beams with decorative, wood dentils. The corner columns have wooden ‘flutes’ and are mounted on brick pedestals. A wood-panelled door is flanked by narrow sidelights and is topped by a transom light. The house has small window openings with low floor to ceiling heights. Small, upper-floor windows are set into rectangular openings with plain, wood frames and sills. A ground-floor, bay window is an angled projection with a hip roof. The brick masonry foundation appears to be a replacement. A horizontal belt line at the top of the foundation is expressed with wood trim. The structure has wood frame construction with stucco cladding and a cut-stone foundation. Bricks found at the bay window foundation and at the entrance porch are probably not original. According to the 2000 inventory, the house is in good condition with many original details. (1, 2, 3, 4)

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 mid-block building located at 10 and 12 Holland St. West was built in the Ontario Vernacular style around 1872-1899. The two-storey, commercial, detached ‘row’ building had a narrow rectangular plan with an asymmetrical organization. ‘Main street’ frontage with a typical storefront façade was located at the street line. The plain façade was characterized by a high, flat, ‘boomtown’ façade and cornice with brick dentils. The two bay-façade each had its own entrance and storefront. Existing doors and storefronts are not original. The original, large, second-floor windows (characterized by segmented arch openings and concrete sills) have been partially bricked in, but are still visible from the brick voussoirs. The building has masonry construction with brick cladding and a flat, built-up tar and gravel roof. (1, 3)
The west side of the building (10 Holland St. West and the location of Pizzaville in this 1995 photo) was once the site of a drugstore run by W.L. "Billie" Campbell. Fred Cook helped him for a number of years. Billie’s son, Lou, and druggist Clarence Ritchie took over the business. Eventually Clarence Ritchie ran it on his own before he retired. Fred McKay sold phonographs on the upper floor and there was a pool room run by James Ferguson. The Salvation Army held services here in the 1930’s. (1, 2)
Sutherland’s Grocery Store was once found at 12 Holland St. West (site of Karen’s and Tina’s Flowers in this 1995 photo). Alec Sutherland was a baker. He had a bakeshop on the south side of Simcoe St. that was run for many years by his daughter Jessie and sister Mrs. Bessie Ryan (and her daughter Betty). They eventually retired and moved to St. Catherine’s. There were living quarters upstairs. William Compton and his wife bought the store and ran it as an IGA grocery store. Gord and Marilyn Compton later took over the store. They built a new store on John St. (where Frank Kilkenny’s house had been). The Comptons’ store eventually moved to what was known as the IGA plaza (located at the corner of Collings Ave. and Holland St. West). As of 2014, 12 Holland St. West is the site of The Holland Bloom florist shop. (1, 2)

The building located at 23 Holland St. West may have been owned by George Stoddart Jr. at one time. It had living quarters upstairs. The ground floor once housed a bank (possibly the Imperial Bank) and there was a large vault in the back. The manager was Fred Stevens. He moved to Barrie when the bank closed. This left the Canadian Bank of Commerce as the only bank in Bradford at that time. The Bradford Witness newspaper, under the direction of Stewart and Ina McKenzie, later moved to this location from the Seim Building. (1, 2)
The building located at 27 Holland St. West also had living quarters upstairs. The ground floor housed the practice of lawyers Gardner, Morris and Denney for a while after WWII. Mrs. Marg Fallis lived upstairs for many years before moving to John Street. (1, 2)

Miss Sinclair’s House is a mid-block building located on the south side at 92 Holland Street West. It was built in the 1890’s in the Italianate style. Miss Bertha Sinclair lived in this house for many years. When she died, her nieces Kay and Isabel (daughters of Robert Spence) moved into the house. They were hairdressers. Isabel later moved and part of the house was rented to George and Ethel Stewart. The building was eventually sold to a real estate agent. The office of Dr. Fitzsimmons was also here at one time. Next to this structure was a vacant lot belonging to the Sinclair family. Many years ago there was a Temperance Hall and a church located there.
The two-storey, rectangular, main building has a single-storey, rear addition, a symmetrical façade, and a moderately-pitched, hip roof with a central chimney. The grand, Italianate scale is reflected in the large window openings, high floor to ceiling heights, and the large, 6/6 sash windows. There are deep, projecting eaves with ornately-decorated, paired cornice brackets and ‘false quoins’ (wood detailing meant to resemble masonry). The window cornices are exaggerated. According to the 2000 inventory, the stone foundation, wood frame construction, horizontal, wood-sided exterior finish (resembling masonry), and painted, exterior, wood trim are maintained well. (1, 2, 3)

This two-storey structure is located at 218 Simcoe Road. It is the fourth house on the west side (south of the “Y” in Simcoe Road). Robert Stewart, his wife, and family lived here many years ago. His son George, who married Ethel Waldruff, played lacrosse and was a painter and paper hanger for Billie Sutton. Robert owned 75 acres of land and worked as the town clerk for 25 years. He also farmed (and later rented) his land. Ed Cave and his wife (Ida) and daughter (Violet) moved to this area from Newton Robinson and eventually bought and worked a farm. He delivered milk and had a dairy in town. Ed was a staunch Orangeman who played King Billie riding his white horse at the 12th of July parade. There was a gravel pit on the property. He eventually sold his farm to Mike Sklencar, John Kulha, Steve Brinkos and John Kashmere. They divided the remaining land and sold the lots along Simcoe Road. The large house was converted into four apartments that were used as their living quarters while they each built a house. The structure was still being used as an apartment building in 1995. (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 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 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)