The major Spanish city was St. Augustine which controlled and encouraged extensive westward expansion on behalf of the monarch in Spain. The need to travel from New Orleans to St. Augustine was the beginning of the Old Spanish Trail which was merely a path in the forest. Eventually, the Old Spanish Trail went all the way to San Diego.

The 455 miles of the Old Spanish Trail in Florida was following trade routes established by explorers and native Americans centuries ago. The 9-foot wide road establish in 1929 became the east section of The Old Spanish Trail.

The Trail follows major portions of Rt. 90, a federal highway from near St. Augustine to Pensacola. Along this roadway are historic cities, events, and places reflecting our heritage. This is truly an old Florida road trip adventure.

Our extensive coverage of St. Augustine, perhaps the most historical city in America is here. The linked blog post details the history and attraction of St. Augustine and we won’t repeat it here. The post shows the importance and significance of the development of La Florida, the Spanish name for lands stretching all the way to New Orleans.

Heading northwest on your Florida road trip adventure,  Rt. 1 from St. Augustine takes us to Rt. 90 just outside Jacksonville. This is the beginning of the Old Spanish Trail in modern times.

The first city you come to is Lake City in Columbia County which is about 60 miles west of Jacksonville. Lake City, formerly known as Alligator, was near the Seminole village of Alligator with the same name. By 1840, few native Americans were left in the area and the town was formally changed to Lake City in 1858.

The Famous Suwanee River

Moving along the Trail west, Rt. 90 passes through Live Oak in Suwanee County. This is the beginning of the tree-lined highway 90, running for miles with mossy oaks hanging alongside the road.

Live Oak is a quaint town that reflects the true south. The habits, accents, and customs of the inhabitants have changed very little over the decades.

A must-visit on your Florida road trip is just on the western edge of Live Oak. The Suwanee River State Park is a beautiful park with a forest-lined river running

through the middle of it. Great place to stop for a picnic and pictures of the famous meandering Suwanee River.

Running from Georgia and cutting southwest through Florida, the river was home to Timucuan and Seminole Indians who inhabited the region for hundreds of years.

Plantation Country in North Florida

Madison, Florida is the county seat of Madison. It is also the beginning of plantation country where cotton farms and large peanut farms stretch for the next hundred miles.

The history of Madison follows the days of slave labor when Spanish, British, and American control was alternating in the region.

It is hard to describe the few miles westward from Madison. There are homes that look like antique stores and poverty seems evident, but this is rural Florida where people find a way to survive and prosper the way they have since the 19th century.

The tree-lined highway hides most of man’s imperfections along the way and gives you the feeling you are traveling in a time warp that only history books reflect.

After Madison, your Florida road trip moves westward to Monticello, the capital of Jefferson county. This area is known for numerous Indian mounds and the historic Jefferson County Jail Museum which preserves the days of a sheriff and

deputy patrolling an entire county. The second story of the Jefferson County Jail was where inmates spent their days.

The town name and county name reflect the days of Thomas Jefferson’s presidency. Monticello is just a few miles east of Tallahassee, the capital of Florida. The terrain, sights, and surroundings become commercial and comparatively unremarkable considering we are following this stunning historic Old Spanish Trail on our Florida road trip.

Florida’s Capital City

History surrounds Tallahassee in Leon County Florida. This native American area is steeped in Timucuan, Creek, and Seminole heritage that will be a subject of a subsequent post.

Tallahassee is the capital of Florida. How this relatively remote city got to be the capital of Florida is full of mystique and bargaining on how the location was selected. 

In another writing, we will tell the Tallahassee story that novels have been written about. For now, we will move on to the small farm town of Quincy, just a few miles northwest of the capital along the Old Spanish Trail.

As the highway unfolds, you will be glad to bypass the hustle and bustle of a modern capital city versus the real rural Florida we are viewing. It’s almost a relief to leave a major metropolitan area.

Somehow mother nature seems to always paint a prettier picture than man’s brick and mortar of a large city.

Tobacco, Cotton and Peanuts – Crops of the Past

Quincy, Florida in Gadsden county was named for our sixth president John Quincy Adams. Quincy was once a bustling agricultural center known for its tobacco crops. While you will see a few stately crops of tobacco occasionally, South American producers began taking over the market in the 20th century.

Quincy still has the look and feel of a southern farm town as it leans on other cash crops that dot the countryside. Many of the plantations have seen their time pass but your imagination can see the class system that brought about films like Gone With The Wind back in the 1930s.

As you move westward on Rt. 90 you are almost a stone’s throw from the Georgia border. In fact, you will come to the little town of Chattahoochee, Florida near Lake Seminole.

We recommenced you take the signs off Rt. 90 heading north for a mile or two and slip across the Georgia border to view this magnificent lake. The dam is a sight to see just a couple miles from the town of Chattahoochee.

The lake is made from the damming of the Chattahoochee and Flint rivers. Florida has been negotiating with Georgia about the quality of the waters flowing from the dam which eventually becomes the Apalachicola River a hundred miles downstream.

There are people who claim the quality of the water is at fault for the collapse of the oyster industry in Apalachicola. The views from the Lake Seminole campgrounds and dam project is worth the stop.

As you go back to the village of Chattahoochee you may be getting thirsty or hungry. Try the WB Sports Bar for refreshments and some delicious wings! A few miles down the road and you will be in controversial Jackson County, Florida on your way to Marianna.

The Jackson County War

History doesn’t treat Jackson County, named for Andrew Jackson, very well. In fact, from about 1869 to about 1875 there were a series of criminal acts that history calls the Jackson County War.

The Jackson County War was a period when confederate soldiers were returning to the area, but not accepting the end of slavery. During this same period, former slaves became free to work the lands as sharecroppers and “freedmen”. Then there was a white oversight group to protect the rights of free farmers. Add the formation of the Ku Klux Klan to the mix, and you have total historic nightmares. People disappeared, there were lynchings, homes were burnt, and murders were never solved.

All the crimes lead one sheriff to resign saying, “there is too much lawlessness for me to do my job!”. Much remained in a tumultuous state clear through the first part of the 20th century when the First World War gave many people more to fight about.

Marianna is the county seat of Jackson County which borders to the north with Alabama. Many say the people up in

the northern part of the county doesn’t know or care where the border is – they just want to live their rural life.

Marianna tries to live down the days of the Jackson County War, but the remnants of civil strife can still be felt along with the name of the county itself being in question. Lately, Andrew Jackson hasn’t fared well in history.

Traveling westward along Rt 90 will bring you to Chipley, Florida and then to Bonifay, Florida. While these two cities are in two different counties they are joined in another way.

Chipley is in a little corner of Washington County and Bonifay is the county seat of Holmes County, but they are linked by just a few miles from each other and this is rodeo country.

Every year the area has the Northwest Florida Rodeo Championships. Partner, that’s a big event every year around these two counties!

History and Ponce de Leon Springs

After leaving Bonifay you will travel through several villages like Caryville and Westville. Both are typical rural communities along The Old Spanish Trail, but “down the road a piece” (southern for a little

distance away) is the town of Ponce de Leon, Florida. To refresh your eighth-grade history class, Ponce de Leon was given credit for exploring the majority of Florida in the 1500s.

In fact, Ponce de Leon was said to have been looking for the fountain of youth.

We are not sure if he found it, but he came close with the springs that share his name at Ponce de Leon State Park just south off Rt. 90. This is another example of Florida’s remarkable state park system.

Ponce de Leon Springs is a perfectly clear spring producing 14 million gallons of water daily with the clarity of a perfect diamond.

Some people say a dip in the 68-degree water will add years to your life! We don’t know if that is true, but the memory of this spectacular park will stay with you for a lifetime! Well worth the stop along the trail the explorers took and you can see why old Ponce stopped here.

As you move into Walton County, you will come across an interesting Town called De Funiak Springs. This community was a commercially built town developed around a perfectly round lake (one of only two perfectly round spring-fed lakes in the world) by the L&N Railroad and its subsidiaries. The intent was to make it a resort, but later it became an educational center.

Some of the old 19th-century buildings still exist around the lake and I must admit I had never seen a beautiful round natural lake become the center of a bustling town. The name De Funiak was the name of an officer in the L&N railroad.

Public Hangings in Crestview

Along the Old Spanish Trail next is Crestview in Okaloosa County. Crestview was another city along the L&N railroad line and got its name from being atop the bluffs of a couple of rivers. The height makes Crestview one of the chilliest places in Florida but offers some beautiful views.

Crestview is also precariously known for two, and only two, public hangings that took place in 1920 and 1921. Both were for murders, but the public hanging of people in the middle of the town was frowned upon by the rest of society.

If being in Crestview makes you uncomfortable, then move on west to near the end of our journey in Milton, Florida.

Milton was once called “Scratch Ankle”. Being a lumber town, workers were used to the briars and brambles necessary to ply their trade, but they named their town a name about what bothered them most – constantly scratching their ankles.

After changing the name to Milton (some say it was shortened from “Milltown” relating to the lumber business), the city became the county seat of Santa Rosa County. The most well-known city in Santa Rosa County is Pensacola just to Milton’s south. Naval air stations in both Pensacola and Milton keep their economies bustling.

History and the Civil War dealt Milton a blow when the Confederate troops were driven from Pensacola by the Union. The Confederates burnt the town down to keep the businesses and industries from falling into the hands of the Union. The city went through difficult times during and after the Civil

war with deserters, protesters,  carpetbaggers, and more descending on the city at various times.

Of course, today Milton stands in the middle of the county and maintains administrative control from the courthouse.

Well worth a stop is the Blackwater River State Park off Rt. 90 just east of Milton. Another of Florida’s park gems that will cost you only $4 for the whole carload of people!

The End of a Colorful Journey

Our journey across the Old Spanish Trail ends here. Just a few miles down the road, the Trail goes into Alabama and begins another tale to be told by another blog.

We know our descriptive terms for the 450 plus miles of your Florida road trip adventure are “beautiful”, “magnificent”, “gorgeous”, “remarkable”, “majestic” and other flowery descriptors. The terms were used numerous times, but there is no way to completely expound on the sights, sounds and views we encountered as we crossed the state on the Old Spanish Trail.

You must experience a different kind of Florida where the salt air is well removed and the white beaches are well to the south. This route is part “old south”, part Florida Cracker country and part of modern-day Florida in the making.

One thing we know is the tranquility of the people in the north Florida country is much like something Norman Rockwell would paint – simply man and nature creating a masterpiece of art and history for the traveler. The Old Spanish Trail is truly a Florida road trip adventure and Mother Nature’s masterpiece.

A Few More Florida Road Trip Adventures From Florida Travel Blog Are Here:

LOOP ROAD – THE ALLIGATOR SUPER HIGHWAY IN THE EVERGLADES