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The Old Photo Review - Classic Old Photos, ads and other cultural artifacts

  • Writer: Old Brooksville
    Old Brooksville
  • Jul 1, 2025
  • 3 min read

Updated: Apr 3

Our 1953 cover photo will bring back many memories of that old orange Gulf sign. This is Webb's Gulf Station, US 41 N. & Old Crystal River Road, there from 1939 until late 1970s. Pictured is Elwood Webb Sr., who began the station in 1939 and remained in business for nearly 40 years. It also served as a convenience store for those near Lake Lindsey and North Brooksville.
Our 1953 cover photo will bring back many memories of that old orange Gulf sign. This is Webb's Gulf Station, US 41 N. & Old Crystal River Road, there from 1939 until late 1970s. Pictured is Elwood Webb Sr., who began the station in 1939 and remained in business for nearly 40 years. It also served as a convenience store for those near Lake Lindsey and North Brooksville.

This issue features our famous Old Photo Review of classic old photos, ads and other cultural artifacts. This issue has photos as far back as 1875 all the way to 1981. It's a grab bag of fun! We hope you enjoy this issue. 2024 will be the start of our 27th year. Thank you Brooksville for keeping our history alive.



Thanks to the following for their contributions


John White

Mary Ann Prescott

George Allen Jr.

Lou Charity


Prohibition Ends!
Prohibition Ends!



1934 Brooksville ad for the arrival of beer at Maillis Recreational Parlor on the side of the Jennings Building on South Main. Prohibition ended on December 5, 1933, and the floodgates opened for beer all over for thirsty Americans.







1938 Hernando High Leopard Football Roster. Notice the beefiest lads weighed on 165 pounds.





Brooksville couple Louis Hope and Winnie Sowers on their wedding day (1882)
Brooksville couple Louis Hope and Winnie Sowers on their wedding day (1882)

Brooksville Orange Packing Plant (1925) on what is now MLK Blvd. This was just east of South Main Street.
Brooksville Orange Packing Plant (1925) on what is now MLK Blvd. This was just east of South Main Street.

1893 photo of May Jennings, wife of William S. Jennings, and baby Sherman at their home on Olive Street. The house still stands. Mr. Jennings would go on to become Governor of Florida in 1900.
1893 photo of May Jennings, wife of William S. Jennings, and baby Sherman at their home on Olive Street. The house still stands. Mr. Jennings would go on to become Governor of Florida in 1900.


William Sherman Jennings came to Florida in 1885 and settled in Brooksville. In 1887, he was appointed circuit court commissioner, and became county judge of Hernando County, in 1888. He was elected governor in 1900.




1959 ad for the City Garage, Brooksville's Chevy Dealer
1959 ad for the City Garage, Brooksville's Chevy Dealer

First Baptist Church (1908) was located on Jefferson Street. Originally built in 1899, the church had its roots in the city as far back as the 1850s. A pastorium in the back was built in 1907. The church was behind what is now Main Street Eatery. It would move to a new location on North Howell Avenue in the early 1970s.
First Baptist Church (1908) was located on Jefferson Street. Originally built in 1899, the church had its roots in the city as far back as the 1850s. A pastorium in the back was built in 1907. The church was behind what is now Main Street Eatery. It would move to a new location on North Howell Avenue in the early 1970s.



1875 drug store on Main Street





1981 Topps football card for Brooksville's Ricky Feacher. A 5'10", 174 pound wide receiver for the Cleveland Browns from 1976 to 1984. The Hernando High grad also held the school record for the 100 yard dash at 9.6 seconds. Lightning in a football uniform.




1968 A&W menu. The A&W was Brooksville's first franchise in 1966 and was a popular drive-in restaurant with teens crusin' the city. It featured Papa, Mama, Teen and Baby Burgers.
1968 A&W menu. The A&W was Brooksville's first franchise in 1966 and was a popular drive-in restaurant with teens crusin' the city. It featured Papa, Mama, Teen and Baby Burgers.

The very first hospital for Brooksville and Hernando County built in 1921 located on Mitchell Road, south of what is now MLK Blvd. Run by nurse Mrs. Boggess and doctors Hancock, Coogler and Creekmore. A new hospital would be built in 1926 on N. Howell Avenue.
The very first hospital for Brooksville and Hernando County built in 1921 located on Mitchell Road, south of what is now MLK Blvd. Run by nurse Mrs. Boggess and doctors Hancock, Coogler and Creekmore. A new hospital would be built in 1926 on N. Howell Avenue.

Hope family home (1893). William Hope was one of the county's first settlers, first arriving in 1842.
Hope family home (1893). William Hope was one of the county's first settlers, first arriving in 1842.


Rare photo (1913) showing the corner of Broad Street and South Brooksville Avenue. The house in the center was Cappleman's Restaurant. The houses lined up behind are on Liberty Street. Photo taken atop the new court house.
Rare photo (1913) showing the corner of Broad Street and South Brooksville Avenue. The house in the center was Cappleman's Restaurant. The houses lined up behind are on Liberty Street. Photo taken atop the new court house.


Looking south on Main Street from Broad Street (1972). To the right is The Quality Shop clothing store, left is the side of the Jennings Building and down the street is Biggart Music. WWJB Radio had their studios on the second floor back then.
Looking south on Main Street from Broad Street (1972). To the right is The Quality Shop clothing store, left is the side of the Jennings Building and down the street is Biggart Music. WWJB Radio had their studios on the second floor back then.

Brooksville's own Fred "Catfish" Abbott, Florida Gator, all-SEC linebacker tackles two mermaids at Weeki Wachee. Abbott would later be drafted by the Minnesota Vikings, but a knee injury ended his football career. He later became an attorney in Jacksonville, where he lives today.
Brooksville's own Fred "Catfish" Abbott, Florida Gator, all-SEC linebacker tackles two mermaids at Weeki Wachee. Abbott would later be drafted by the Minnesota Vikings, but a knee injury ended his football career. He later became an attorney in Jacksonville, where he lives today.


Perhaps the earliest picture of Broad Street (c. 1903). The Jennings Building is to the right. Considering that telephone service began in Brooksville in 1900 and the pole has only one crossarm, this photo may be as early as 1901.
Perhaps the earliest picture of Broad Street (c. 1903). The Jennings Building is to the right. Considering that telephone service began in Brooksville in 1900 and the pole has only one crossarm, this photo may be as early as 1901.


Rare photo of train arriving toward Brooksville (c. 1885). Locals pose near an orange grove as they await with excitement the train coming into the city.
Rare photo of train arriving toward Brooksville (c. 1885). Locals pose near an orange grove as they await with excitement the train coming into the city.



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