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The building located at 1 Holland St. East (on the northeast corner of Holland and Barrie Streets) is part of what is known as the Green Block. The structure was originally owned by Mr. Green, who lived with his family on the west side of Church St. in the hotel. The Masonic Hall is still found upstairs at this location in 2014. (1, 2)
Many businesses have been located at 3 Holland St. East (on the northeast corner of Holland and Barrie Streets) over the years. They include a grocery store, a boot and shoe shop (run by Charlie Wilson), an insurance company (that was later run by Fred Cook), a delivery service for C.N.R. (first by horse and buggy, then later by Model T Ford), a hamburger stand (run by Harold ‘Butch’ Boyd), and a telephone office. The first private telephone came to Bradford in 1885 and was run by a number of businessmen. There were ten phones only for Bradford. A garage was later added at the back at the laneway for trucks and cars. (1, 2)

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 structure located at 29 Holland St. West was vacant for many years. Howard Bowser bought and restored it as a shop with living quarters upstairs. Ted and Audrey Gapp lived here for a number of years. Helen Bantam ran a ladies’ shop downstairs and lived upstairs. She may have bought it from Bowser. At the time of this photo (1995), it was a barber shop.
The building located at 31 and 33 Holland St. West (on the northeast corner of Holland and Moore Streets) was built around 1880 in the Ontario Vernacular style. It was constructed on the site of the former Edmanson Bakery (33 Holland St. West). The bakery was the origin of the big fire on May 23, 1871 that destroyed much of downtown Bradford. E.P. Snow had a harness and saddle shop at 31 Holland St. West for many years. He lived on the north side of John Street. Later it was bought by Secondo Cavallo, who ran a shoemaking business at this location. He lived on the south side of John Street. Cavallo’s daughter (Aida) ran the business for a few years and then it was sold. Lash Davey and Bill ran a butcher shop at 33 Holland St. West for several years. They had a slaughter house on Piccadilly Hill (Simcoe St. South). James Webb, a butcher and lacrosse player, later ran his shop here. Webb was joined by his son Jim, who eventually took over the business and employed Harold Boyd. Jim originally had an ice house at the back of the property. A freezer locker was built later by Len Saint at the back. The building and business were eventually owned for many years by the Pezzanitti family.
The one-storey, commercial, semi-detached ‘row’ building has a wide, rectangular plan with an asymmetrical organization. There is “Main Street” frontage with a typical, storefront façade located at the street line. A plain façade is characterized by a high, flat, ‘boomtown’ façade with brick dentils. The two-bay façade is dominated above the storefronts by an applied, pressed- metal cornice with stone brackets at each end. Existing doors and storefronts are not original. Wide, glass, storefront windows with stone sills are also not original. The building has masonry construction with brick cladding, a stone foundation, and a flat, built-up tar and gravel roof. According to the 2000 inventory, the modest building is in good condition. (1, 2, 3)

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)

"No cause has yet been determined for a stubborn blaze which broke out in a house at 16 John Street East in Bradford last Tuesday.
The Bradford Fire Department was called out at about 4 pm to quell the blaze which broke out in a back apartment, occupied by Dick Gullinger.
Fire Chief Harold Boyd said the whole apartment was in flamed by the time the firefighters arrived on the scene, and there was no hope of saving it.
The back wall of the house was also badly damaged, and thick smoke made the rest of the house uninhabitable for the occupants of the other two apartments, John Faria Jr., and Louis Dasiba.
"It was a tough one to put out," Chief Boyd said, explaining there were many false ceilings in the old house which had to be torn away to get at the flames.
The chief estimated it took about three hours to put the fire out. The occupants managed to remove most of their belongings during the blaze, and there were no injuries. There has been no estimate of damage."

Fire chief Harold "Butch" Boyd. This photo accompanied an article about his death at the age of 64 which appeared in the Bradford Witness.

"The Bradford fire department has a new fire chief to fill retiring Chief Ted Gapp's place.
The 16-member volunteer department voted Monday night to recommend that council appoint Deputy Chief Harold Boyd as new head of the department.
Mr. Boyd, who has served on the department since 1943, was the members' unanimous choice for chief.
Boyd became deputy chief in the late 1940's shortly after he joined the volunteer brigade. He also held the secretary-treasurers' post under Chief Dodger Collings.
The new chief first came to Bradford in 1937. He was born in Newmarket.
For the last two years, he has been semi-retired and he told The Witness that he will devote much of his time to the department and his new post.
In addition to electing a new chief, the volunteers elected Ed Bulpit as the new deputy chief.
Other officers elected Monday night were: Bev Everitt, secretary; Jim Church, treasurer; Ron Bannerman, Laurence McKnight and George Lowe, captains.
Chief elect Boyd was scheduled to appear before council Tuesday afternoon to receive his official appointment.
Boyd will take over the job Chief Ted Gapp is leaving this month after 35 years as the department's head man."

Bradford fire hall with many volunteers. Volunteers were the only source of fire fighters in those days.
From left to right: Roy Storey, Ted Gapp, Roy Saint, Bill Beekink, Gord Church, Jim Church, George Allan, Jim Everitt, Gord Compton, Orville Hand, Harold "Butch" Boyd, Chuck Woodcock.

"Lavish was the praise Monday night as approximately 200 Bradford residents gathered at the community centre to pay tribute to nine firefighters who have each given more than 30 years of service to the town..."