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Stop 3 & 4: The 1908 Sunnybrook Tobacco Plant/George Massey Building and 1926 Osceola Hotel

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Two ghostly building sites!


     As you meander to the east from the inspirational gazebo, you will be heading toward the new city hall/city police office. Gaze across Meridian to the north and notice the large parking lot to the right/east of the Wells Fargo Bank, basically at the intersection of 7th Street and Meridian.  That was the site of heaps of activity in early Dade City. 


     A related question…In 1908, what would you imagine was the largest crop in the area? Well, tobacco, especially cigar tobacco was the major industry and crop. The largest firm in the area was Sunnybrook Tobacco Company which was housed at the site you are perusing. 


     Dade City tobacco industry even won first prize at the state fair and was virtually unbeatable in its quality. 


    Sunnybrook employed 100 workers when George Massey arrived in town and its crop valued about $80,000. Just after his arrival, the company reached a capacity of 21 barns. (Barns were typically 60 by 120 feet long, similar to greenhouses. This building once known as Sunnybrook and later Massey building was used as a processing plant for tobacco in downtown Dade City).  The building was later acquired by the adjoining bank and you will see it metamorphize over time in historical photos and accounts as it housed offices and businesses, many of which are a part of the tour…the library, real estate, medical/dental offices, professional offices, as well as space for the early National guard. It also hosted regular dances and community events.


     Tobacco was planted in the spring in fields that were covered with netting to shade, and was harvested in the summer. The average yield was 1,000 pounds per acre. Nature was not kind to the tobacco industry in an era, long before many recognized the negative health effects of tobacco. A 1921 hurricane blew down all of the tobacco sheds and …a disease known as Black Shank struck quickly in 1922, attacking the stems of the tobacco leaves. Tobacco growing never returned to Dade City.


The Sunnybrook/Massey building was torn down in 1989 as part of a downtown renovation.  


     Okay now, slowly spin back around and walk towards 5th Street. Imagine the Osceola Hotel, at the southwest corner of Meridian and Fifth.


      Helen Eck Sparkman wrote, “No account of early Dade City would be complete without reference to the Osceola Hotel, built in 1905 by M. L. Gilbert as a boarding house for workers of the Sunnybrook Tobacco Company.”


    Later, the popular hotel was purchased and operated by Mrs. Douglas Cochrane, whose daughters (Inez, Ethel, and Lula) and sons (William and Fred) were popular members of the younger set. The Osceola, both as a hotel and as a boarding house, became a home away from home for visitors and local people, housing tobacco workers and many other newcomers over time.  One of the most beloved figures of the town was Rose Fyffe, known to all as Aunt Rose, who succeeded Mrs. Cochrane. 


     The Osceola was razed to give room for a convenience store and that store gave way to several other businesses over time.

  • 1898

    Estill Boone Embry moved to Dade City to grow Cuban and Sumatra tobacco.

  • 1899

    Cigar factory was exceeding expectation with plans to hire fifty cigar makers (Dade City News).

  • 1905

    Osceola Hotel was built by M.L. Gilbert as a boarding house for workers of Sunnybrook Tobacco Company.

  • 1906

    Estill Boon Embry owned the largest tobacco farm in Florida…with thirty acres of tobacco under shed, Embry closed a ten-year contract for tobacco crop at 40 cent a pound; advertised work for 400 men, women and children in the tobacco production.

  • 1907

    With 8 successive crops of tobacco and now five hundred acres, Embry perfected growing crops under lattice shade structure to produce fine texture. He also organized capitalists who paid on capital of 100,000 Rosenfield Brothers, Sunny Brook Distillery Company.

  • 1907

    Sunnybrook Tobacco bought out Embry Tobacco; Sunnybrook became the largest employer in Pasco County.

  • 1909

    Oct. 30, 1909. The Gainesville Daily Sun reported Embry. manager of the Sunnybrook Tobacco Company, reported that Florida wrapper tobacco was bringing two dollars a pound.

  • 1912

    George B Massey arrived in Dade City from Ohio with family; executive of Sunny Brook Tobacco Company.

  • 1912

    The Osceola Hotel was listed as one of three hotels in Dade City; a capacity of 20, te rate was $2.50 per day.

  • 1921

    Hurricane destroyed tobacco sheds in Dade City.

  • 1922

    Incurable fungus disease of Black Shank (Phytophthora nicotianae) attacked tobacco crops and wiped them out.

  • 1924

    Fire destroyed the three-story Sunnybrook Tobacco Co. building in the worst fire in the history of Dade City. 150,000 pounds of fine wrapper tobacco valued at $200,000 was destroyed.

  • 1925

    George B. Massey passes away.

  • 1930

    Estill Boone Embry passe away.

  • 1957-1959

    Newspaper advertisements: 15 rooms with 2 three-room apartments; corner property 90 feet by 100 feet; next to the courthouse, city hall; Osceola Hotel for $20,000 or swap.

  • Circa 1965

    Osceola Hotel torn down.

  • 1989

    Sunnybrook/Massey Building was torn down.