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The mid-block building located at 37 Holland St. East was built in the Gothic Revival style in the 1880-1890’s. Originally, the left side on the ground floor contained an office occupied by grain buyers. It had a front door and a small window. The remainder of the building was used as living quarters for several families over the years, including Art Hand (a painter and decorator) and his wife (Sawyer), and later their son Orville and his wife Helen (Noble). It was eventually sold to Mr. Glass, a merchant.
The 1½-storey house has an ‘L’-shaped plan with a centre hall. It also has an asymmetrical façade, an off-centre front gable at the façade projection, and a medium-pitched, gable roof. There is a raised, open porch. The existing roof, supports, and railing are not original. Its wide door opening suggests that the original had a transom and sidelights. The door itself is not original. There are small windows with high floor to ceiling heights. Wide windows set into rectangular openings in the projecting bay are not original and the variation in the brick suggests that the original openings were partially bricked in. The windows in the receding bay are set into segmented, arch openings with brick voussoirs and concrete, lug sills. None of the existing windows are original. The building has wood frame construction with brick cladding and a textured, concrete foundation. According to the 2000 inventory, there are few original details remaining in the building. (1, 2, 3)

The mid-block structure located at 83 Holland St. East was built in the Ontario Vernacular Cottage style. It was constructed pre-1900 on what was once the site of a pop manufacturing plant. According to local history, bottles were still being unearthed many years later. After the plant closed, the property became the site of a blacksmith shop run by Bill Cukens. The house seen in this photo originally had a back kitchen and wood shed at the rear, as well as a large, two-storey barn with loft above (for horse feed). It was the home of Bob McKinstry, his wife and children Michael (Mike), Maisil, and Dorothy. Bob was a huge man and a blacksmith for several lumber companies after the local mills folded. He was also a noted field lacrosse player on the team that won the championship in 1905 (1907?). Bob and his son both played lacrosse until their worn-out legs forced them to quit. In those days, lacrosse players worked ten-hour days at hard physical labour, played lacrosse for a couple of hours, and then ran the six miles to Bond Head to cool off. Mike was a bookkeeper who also worked for his father in the garage and blacksmith shop. Maisil became a nurse and Dorothy worked in a restaurant and stayed at home to look after her family.

The one-storey, three-bay ‘cottage’ has a rectangular plan with a centre hall, a symmetrical façade, and a shallow-pitched, gable roof. The enclosed porch has a hip roof and the entrance is raised above grade level. There is a simple entrance with a single door with windows on each side. The porch stairs are not original and the entire porch may be a later addition. There are double-hung windows at the ground floor. The 2/2 widows appear to be original and are set into simple, rectangular openings with plain, wood surrounds and sills. Exterior aluminum storm windows are a later addition. The building has wood frame construction with vinyl siding and a stone-rubble foundation. It had wood cove siding originally. According to the 2000 inventory, the building’s form is one of the few existing original building elements. It also notes that the modest cottage probably had few decorative details originally. (1, 2, 3)

The building located at 1 Holland St. West was originally built as a hotel (Central Hotel, Uneeda Hotel, H. Hulse Hotel). Tom and Len Saint worked on the construction of the building. George Webb ran the hotel for a while before he moved to Saskatchewan. Tom Bell was the manager for many years until he retired and moved to the east side of Simcoe Street. Around 1917 it became the Imperial Bank of Commerce. A large safe and living quarters for the bank staff were located upstairs. The entrance to the apartment was on the west side of the building. John McDowell and his family lived here in the 1930’s. The bank was robbed by the notorious “Boyd Gang” in the 1940’s. At one time the front offices were used by the police, and the back offices were used by Mr. Scanlon (a lawyer). The bank closed in 1972 and was moved further west on Holland Street. This building then became a real estate office, a convenience store, and as of 2014, the Coffee Culture Café. (1, 2)

The original building located at 4 Holland St. West (on the southwest corner of Holland and Simcoe Streets) was built in the 1840’s and was situated on land originally owned by James Drury. He was one of the early immigrants who reached Upper Canada. Drury rented the corner lot to Thomas Driffill (a blacksmith), who opened a hardware store at that location. The lot was later sold to Robert Cooke, who leased the property to Driffill for another 20 years. Thomas Driffill became the village of Bradford’s first reeve when it was incorporated in 1857. The great fire of 1871 destroyed all but the building’s foundation. It was rebuilt incorporating the intact, old vault and locally-made bricks. Thomas Driffill bought the building in 1885, eventually retired, and left the business to his sons, Joseph and James, who eventually sold it to Andrew Thompson, Driffill's partner. It became Thompson's Hardware. A series of different owners and different types of enterprises followed. William Barron bought the building in 1946 and relocated his hardware business to this site. He made several renovations, including adding a new stone façade, new plate glass windows, and an elevator to facilitate deliveries to the tinsmithing shop upstairs. He retired and left the business to his son Norman. The building later became a motorcycle shop, and eventually, for several years, the Winchester Arms Restaurant. (1, 2, 4, “Four Holland Street West: A Short History” by Lorraine Philip - Bradford West Gwillimbury Public Library, Local History Collection).

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)

The building located at 30 Simcoe Road was known as the Lathangue & Skwarchuk Funeral Home when this photo was taken in 1995. The Kilkenny family was the first to serve Bradford with a funeral home in 1836. Neil Lathangue owned the business from 1950-1963. Mac Lewis was the owner from 1963-1973. He brought Bill Skwarchuk into the business in 1968. Today (2017), the funeral home is owned by Bill Skwarchuk and his family. (1, Skwarchuk Funeral Home web site)

"On the eve of his 92nd birthday, Tuesday, Bill Ruffett told the story of the booming ice industry of yesteryear. Bell Ewart - "I started on the ice when I was 12 yeards old. Father had rented the old hotel on the south side of the dock of 1897 for one dollar a month. After the old sawmill had burned down, the hotel went out of business. I remember well tearing out the bar. It was then I started to lead a horse on an ice plow for 50 cents a day for the Belle Ewart Ice Company. It was the only ice company there then and was across the road from my home where Sheppard's Marina is today. I remember the winter of 1906 was very mild and the big lake never froze over until nearly spring. The railroad was still here, you see, from the era of meeting the Lake Simcoe excursion boats. It was then ice companies from Jackson's Point came here, partly because of the railroad. Their only transportation there, for ice to Toronto, was by street car. I had anywhere from 60 to 80 men working for me at one time, all farmer's boys."

This structure is located at 11 Barrie Street. (1)

Many businesses have used the flat-roofed structure located at 29 Barrie Street. It was once the home of a farm machinery business run by Reuben Tindall. When he retired, he sold the business to Dick Crake. Dick, who sold machinery and 28 Chevrolet cars, was a bachelor who did not drive. Allen Ceeiry(?) was his chauffeur. Dick had one of the first radios in town and his shop was a popular hangout for farmers and teenage boys who wanted to listen to hockey games. Dick ran the business until he retired. Then John Morden (from Kirkland Lake) started a body, fender, and paint shop at this location which he ran until his death. A businessman from Bond Head ran a blacksmith shop here for a period of time after WWII. (1, 2)