St. Augustine, Florida, was founded in 1565 by Spanish explorer Pedro Menéndez de Avilés, it is the oldest continuously inhabited European settlement in the continental United States. With its stunning architecture and vibrant culture, St. Augustine offers a captivating look into life during Spanish rule. This post will take you through the significant aspects of this era, spotlighting its unique architecture, daily lives of its residents, and cultural exchanges that helped s

It was a hard decision, but we narrowed it down to our Top 25 covers of the print version of Old Brooksville in Photos and Stories. We began in 1997 and in 2026 we will celebrate our 30th year. There are a total of 328 issues so far and our goal is to get them all up here for your enjoyment. In the meantime, we hope you enjoy The Top 25 Covers of Old Brooksville listed here in no particular order.

Jefferson Street (1913) looking east. The bank building on the left still stands as Truist Bank. The famed Varnada Hotel is down the street. Carriages and early cars are few on the new brick streets that Sunday. There have always been three main streets in Brooksville, Main Street, Broad Street and Jefferson Street. We have done pictorial and historical essays on Main and Broad in the past but never one exclusively on Jefferson Street. This issue brings photos covering nearly

1952 ad found in a Brooksvile magazine shows the efforts of cigarette manufacturers to allay the fears of consumers after it was proven that smoking causes cancer. Other manufacturers would also feature movie stars, recording artists and famous sports figures touting how safe they were. Advertising has always held a special place with me. I majored in Advertising/English at the University of Florida in 1968 and have been involved in it ever since. As a kid, I was always fasci

The newly paved State Road 5 (later to become US 41) 1925. This is South Broad Street heading north into downtown. The Road. The road is the road of life. It leads us to many cities and towns across America. Each one leading to an adventure in our lives. This is a pictorial essay of the development of roads in Brooksville and Hernando County history. From dirt roads of the 1800's to the roads we have today. It is the old roads and US or state highways that capture the charact

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. Th

Starting our 28th year takes us back 100 years to 1925. 1925 may be the most prosperous year in Brooksville history. The economy was at an all-time high, new towns were springing up around Brooksville, homes were being built, many businesses boomed including citrus and the rock mines, and major roads were being paved making 1925 the high-water mark of the roaring 20s in general and throughout the nation as well. By 1928, the Florida boom had died, a precursor to the stock ma

This issue covers how the train changed Brooksville with a pictorial history of train travel in Brooksville and how it spurred our growth tremendously, not only here, but across the nation. We all know how it gave birth to cattle drives from Texas up or Kansas with the newly formed railroad lines connecting directly to Chicago and New York. The same thing in Florida, enabling the citrus and tourist industry to flourish and later on for the rock mines as well. Train travel was

The Wild West gave us many bad men in folklore. In the history of the west, there was no one as despised, feared and prolific a killer as John Wesley Hardin. Legend has it he killed at least 44 men in his lifetime. An 1873 news item in a Savannah, Georgia newspaper led us to this story of his visit to Brooksville, Florida where he killed a man. It is amazing that the deadliest killer in western history would visit Brooksville. Here is the rise and fall of John Wesley Hardin.

The famed Trieman House (originally Coogler House) 1913 Brooksville, a quaint town tucked away in Florida, offers a captivating history...