Yesterday and Today Along Jackson’s 1818 Route Across the Panhandle

It is hard to believe this is the last day of 2018. In some ways, it went by too fast, and in others, it truly crept. But it will officially be gone in another few hours. I do hope everyone has had a safe and wonderful holiday celebrating with family and friends.

I’ve been busy this year working on a new book. This one on the history of the Upper Yellow River area in what is now Okaloosa County. In researching the early history of the area, I became interested in the route that Andrew Jackson was supposed to have taken in his march from Ocheesee Bluff to Pensacola. I’ve been hearing about him traveling through Oak Grove since I was a kid. Tall-tails put them marching along the public trail that used to be just south of Stewart Cemetery (which did not exist at the time) and all through the community that was just beginning to be settled. And then I was contacted by a man working on an app of historical sites in Florida and we got to talking about the route. That rekindled my interest. I posted the map in a previous post on the Seminole Wars but I want to explore the route in a bit more detail and develop a route for family exploration on a nice Spring day. It has been a bit over 200 years since Jackson made that trip, ending in Pensacola and setting the chain of events into motion that would transfer the territory of Florida to the United States.


Before we try to lay out the route on today’s map, let’s be clear on what we are viewing. This map was not created in 1818. It was created by Mark Frederick Boyd sometime during his lifetime (1889-1968). According to the small print just below the dotted line that represents the reported actual route, Boyd used Searcy’s map of Florida from 1829 to generate his map. While it is helpful to have the names of some locations on the map, the majority of those locations did not exist as places with that name at the time that Jackson and his troops made the march. The other important point to keep in mind is the “roads” that may have existed for some of this route were likely just well used Indian trails, they were not roads as we think of them today, not even our wonderful Florida dirt roads we are all familiar with. The final observation about the map is geographic markers are not always in proportion to the map or each other.


The map begins the journey on the banks of the Apalachicola River at Ocheesee Bluff/Landing so that is where I began mapping points on Google Map Pro with some assistance from Google Maps online. That required a fair amount of moving back and forth between an enlarged version of the Boyd map and Google Map and zooming in and out in Google Map. It got easier as I moved closer to the parts of the Panhandle I’ve trooped around in the most. From Ocheesee Landing the route travels northwest to just east of what is now Marianna where Jackson’s troops crossed “Big Spring” which may well be Merritts Mill Pond on today’s map. Next, they marched north of what is now Marianna and crossed at Natural Bridge. Now there’s a good picnic spot during a day trip.

The next section of the journey took them in a meandering march across the northern part of the Panhandle above what is now Chipley and Bonifay to the approximate area of Hwy 2 where it crosses the Choctawhatchee River. At this point, you get the impression from looking at the map that they were trying to angle north of the Shoal River and all of its branches. They moved along the Florida/Alabama line for a while and then moved into Alabama and traveled along the border above Florida until they reached Lake Jackson in what is now Florala, AL.

Here they marched back into Florida and traveled near what is now Svea on Hwy 85 and continued on to the Yellow River, crossing where the river was narrow and John Barrow would install a ferry within a year or two. It is likely that the crossing was already an Indian trail and used by Natives and an obvious place for a settlement. In talking with my Mom about the early bridges she remembers, and reviewing the aerial maps done by the military in the early 50s, it is likely that the ferry and early bridges were just south of the existing Highway 2 bridge.

1955 Flight 1N Tile 8 Old Road in front of GP

After crossing the Yellow River, Jackson and his troops make a somewhat straight line southwest to somewhere near modern-day Pace. Here they must have arrived at a location Jackson felt was not conducive for crossing and they turned north and followed the river until east, southeast of what is now Cantonment and crossed there. They marched straight across to what was likely a “road” the Spanish used that headed north out of Pensacola. Highway 29 is probably situated very close to this original road. They were now on a straight route into Pensacola and with Jackson’s usual manner, he took Pensacola, at least briefly. However, talks had already begun to sell the territory to the U.S. The Spanish protested Jackson’s confrontation and demand for surrender and withdrew from negotiations briefly, but in the end, Florida was transferred to the U.S. officially in 1821.

As I mentioned at the top, I often do this kind of digging to develop a fun route for a family outing. So, sometime in 2019, I will provide a driving route that comes as close as possible to Jackson’s route and points out some interesting stops along the way. I find this a great way to get a bit closer to our Panhandle history and did some of this in my book on the 1st Florida Union Cavalry and their several long marches. When I was growing up, it was a thing we did to get out on Sundays after church and go explore some part of our surroundings and have a picnic. It’s a shame this isn’t a routine that survived “progress”.  It is so much more fun than reading about it or staring at a smartphone.

Until Next Time


One thought on “Yesterday and Today Along Jackson’s 1818 Route Across the Panhandle

  1. I had read A. Jackson and troops had a battle just North of Milligan —River Rd. area. About a mile north of Hwy. 90.
    During that research I went there to see where. Years ago now—would have to try to remember what, where and what book I was getting the info.

    Liked by 1 person

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