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Stop 53: Historic 5th Street Entrance into Dade City

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Historic 5th Street (Bonus Stop).


    To fully understand the development and evolution of Dade City, it is important to understand see the earliest traffic patterns as 5th Street was the main thoroughfare through Dade City until the 1950s. 7th Street was elongated much later to accommodate the development of 301 and the main thoroughfare through the town moved from the eastern side to a more central location.


You will find an array of historical houses documented in both Melody Floyd’s Chamber of Commerce historic house tour list and Madonna Wise’s Images of America: Dade City as well as some businesses on 5th Street. The southern end includes a brick street. Many of the houses date back a hundred years and show different aspects of Florida building styles and historic structures. In Stop 47, you learned about the Sears & Roebuck kit house, and of course, crossing over Meridian, heading north, you would see the ice plant and steam plant on the eastern side.


   The Crescent Park developed by I.M. Austin, Knapp, & Wakefield Company was a huge new subdivision in Congress Park of Dade City. The new Woman’s Club building and the Crescent Theatre added to the swanky ambiance. A front-page Dade City Banner of March 11, 1926 persuaded many to purchase lots. 


Situated on the gently sloping side of one of the highest hills in the southern part of Dade City, its location for residence purposes cannot be surpassed. The developers of Congress Park started out with a dream. A lot on easy terms in this park will give you a bank account in future years. Every lot has sidewalks, water, electric lights and are located in Dade City’s business and best residential section.” 


   Historically, 5th Street was referred to as Wire Road (Road Number 3). The federal government built a telegraph line from Ocala to Tampa along the public highway which was known as Wire Road. A portion of Wire Road is still viable and can be accessed from 301 between Dade City and Zephyrhills.


     Wire Road took the route of today’s 5th Street through Dade City from approximately the intersection north of town where River Road intersects the bypass. Exiting Dade City to the south, Wire Road took the route of today’s 301 from Dade City to Greer’s Hill and then into Zephyrhills.


   Just as the early town had been moved south to accommodate the railway into town, the shifting roads tweaked the business center of Dade City. A 1926 bond issue of $40,000 was approved to open up 7th Street to the north limits of Dade City. As you garnered from verbiage about Meridian Avenue and the brick paving in Stop 48, the building of roads was paramount to accommodate the motor cars and trucks.


     Tampa Daily Times of November 23, 1923 reported on the utter jubilation at the opening of State Road 23, the completed section of the national highway. The Pasco County Commission hosted an opening of Dade City to the outside world with a motorcade and fake isolation walls made out of netting from the tobacco plant that the cars drove through in a kind of metaphor of opening up Dade City. A huge barbecue prepared by Charles Edwin Dowling, who later served as a Pasco Sheriff for seven years and a Pasco County Commissioner, cooked up a huge barbecue that was said to feed thousands. The completed section of the national highway, a section of State Road 23 was cause for a huge celebration.


    Later in 1951, 5th Street took another hit as it was reset as part of the bypass. A report showed that almost 2,000 commercial vehicles entered and exited Dade City at the junction of River Road and 301. The consensus was that a bypass around town would better utilize 7th Street. 


   Times were changing and a trek into Dade City was now via U.S. Highway 301/7th Street rather than the previous 5th Street. 


    Some of the businesses on 5th Street that were repurposed  included The Crescent Theatre (STOP 44) the Milton Funeral Home (STOP 74) and an array of other historical houses which included: 1) the 1920’s Mills House at the Southwest Corner of 5th and Howard; 2)  the 1894 Cooper-Massey House at the southeast corner of 5th and Florida;3)  the 1920’s Arthur Burnside House at the northwest corner of 5th and Palm; 4) the 1925 Bessenger house at southwest avenue between 5th and 7th Street; 5)  the Touchton Tourist House at the Southeast Corner of 5th Street and Meridian; as well as 6) the Roy D. and Clara Guymon Home (the Milton Funeral home space.


The lovely historical houses on 5th are great to peruse and represent a part of Dade City. 

  1. The 1920’s Mills family home with address of 13945 5th Street (pre 911 address of 503 South 5th Street).  Drew B. Mills was a proprietor of the Dade City Hotel in the early 1900s. Revisit Stop 28 to learn more about the Dade City Hotel which was built in the 1880s and succumbed to fire in 1909.
  2. The 1894 Cooper–Massey Home at 13820 / 13848 5th St (previously 708 S 5th St) at the southeast corner of 5th Street & Florida Avenue was built as a winter home for Gus Cooper. A small clapboard structure with the framework visible on the exterior. It was purchased by George and Julia “Daisy Massey in 1912 and they enlarged it. Later the roofline was redesigned to appear more like an English cottage. 
  3. The 1920’s Burnside house was built by Arthur J. Burnside, circuit court clerk for 40 years. His family’s home at the NW corner of 5th Street & Palm Avenue.
  4. The 1925 Bessenger House at 37931 Southview Avenue between 5th & 7th Street was constructed in a Cuban-Spanish design. Following hurricane damage, a pitched roof was installed around 1950. Sheriff Leslie Bessenger and Pearl Bessenger, bought the house after the Great Depression. Pearl lived in the house for over seventy years. The house faces Miss Polly Park to the south.
  5.  A 1923 post card represents the residence of C. F. Touchton at the SE corner of 5th and Meridian. Later Tampa Electric was located here, the house is no longer standing. Stops 52 and Stop 60 will provide further information about the contributions of the Touchton family.

       6. The 1925 Anna Lee Edward Guest House that became the Milton Funeral Home at 13950 5th Street (pre-911 address of 502 South 5th Street) housed the Milton Funeral Home since 1978. (Find more information at Stop 74).

  • 1887

    Wire Road approved by County Commission.

  • 1923

    Celebration in the opening of State Road 23, the completed section of the national highway which hosted an opening up of Dade City.

  • 1925

    Crescent Subdivision is platted.

  • 1926

    Dade City Woman’s Club Building built in the Congress Park area near 5th Street.

  • 1926

    Bond issue of $40,000 was approved to open up 7th Street to the north limits of Dade City.

  • 1948

    Business and commerce on 5th street was waning.

  • 1951

    Part of 5th Street was folded into the Dade City bypass.

  • 1959

    Dade City Garden Club purchases land on 5th Avenue for Garden Center.




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