DeSoto’s Route across the Aucilla River to Tallahassee

Canoeing the Aucilla

De Soto’s Route across the Aucilla River to Tallahassee 
This route can only be completed on a map these days,
but it essentially follows the descriptions given
by the five dairies of participants in DeSoto’s
route through Jefferson County, Florida.


Take the low road, sometimes called the “Old Mission Road” south of Madison, Florida toward the Aucilla crossing. You pass through San Pedro Old Fields, an area of fertile pasture dotted with stately live oaks draped in Spanish moss. A historical marker is beside the road near the Mission site.

Spaniards with De Soto reported marching through a “great woods” and then spending the night in a piney woods. The following day they came to the village of Agile on the east bank of the Aucilla River.

The San Pedro Old Fields were probably a “great woods” when De Soto marched through in the sixteenth century. There is no true pine forest on the route, but the area around Greenville is mixed woods with a lot of pines. It is possible the six-hundred-man Spanish army with their host of servants, captives, hogs and horses slept in those woods the night before they reached Agile.

When the Spaniards crossed the Aucilla River they described a swampy area and much more water than we find now, but there is no doubt the Aucilla River is the eastern boundary of the province of Apalachee. It fits the Spanish record.

Follow a dirt road south along the riverbank to the railroad. The Apalachees continuously fiercely attacking the Spaniards as they moved through a narrow track in the woods and “red hills of Apalachee” toward the present town of Aucilla, probably the site of the Apalachee town Ivitachuco.

Country Road 158 follows the railroad track, and railroad tracks often follow the oldest roads. Continue on this route to cross U.S. 19 at Drifton to move on to Lloyd, in Jefferson County. The Spanish described a “deep ravine” in this area where the Apalachees seriously attacked them. Just east of Lloyd you cross a short bridge over a deep ravine with steep banks and a substantial stream of clear brown water. It exactly fits the Spanish description.

Route 158 continues west through Lloyd to Capitola, four miles west. Great live oaks crowd the road and the roadbed is cut deep with long use. Next is the tiny town of Chaires, still on an old road that in historic times served as the main road from Tallahassee to St. Augustine.

In Chaires you go south to Route 27 then turn left back east a short distance to take a dirt road to the right marked “St. Augustine Road.” This road heads south when you leave Route 27, but soon bears around to the west. Bordered by huge old live oaks that create a dense canopy, the roadbed has gouged deep into the earth, indicating many, many years of use.

Tallahassee is about ten miles farther west. After nearly five miles of dirt the road is again paved. As you enter the outskirts of Tallahassee a marker announces you are on the “Old Spanish Road.”

(see Hudson)Old Road