Take a Scenic Drive through the Red Hills

by: Doug Alderson, Outdoor & Nature Expert

Canopied trails are my favorites, whether it is the wild corridor of the lower Wacissa River Slave Canal, the multi-use path of the Tallahassee-St. Marks Historic Railroad State Trail, or the many canopied roads north and east of Tallahassee through the Red Hills region.

On a recent weekend, I headed out to visit a friend in Greenville, about 45 minutes east of Tallahassee, so instead of taking a direct route, I first aimed northeast on Centerville Road. Soon after leaving Capital Circle, arching live oaks seemed to embrace the road while neighborhoods gave way to pastoral horse farms, vintage barns and country churches. I merged onto Moccasin Gap Road near the historic landmark of Bradley’s Country Store, founded in 1927, and made my way to the tiny town of Miccosukee. Here is where things got really interesting. Heading north on Highway 59, I entered plantation country, vast and rolling. More than a century before, cotton fields gave way to pine forests so wealthy northerners could create an ideal environment for quail hunting. I pulled over at the entrance of one plantation because blooming magnolia trees lined the entrance road. The sweet fragrance felt refreshing. I knew the place was private, but it’s okay to enjoy someone else’s garden, if only for a few moments.

I eventually made my way to Old Magnolia Road, a clay road that is heavily canopied. This didn’t show up on my general map. Where would it lead? As the road cut deeper, the embankments became higher, moss covered and studded with roots, the red clay contrasting with bright greens. My senses became heightened as I anticipated each new bend. My drive had turned into an adventure.

At the Dueling Oak crossroad, the site of a famous 19th century duel, the road divided around a massive live oak bordered by a low brick wall. This was obviously a deliberate move by someone generations ago and I appreciated their flexibility in leaving the patriarch oak, one that had been growing since before statehood. I learned later that the Old Magnolia Road was once a major route to transport cotton, so it is sometimes referred to as the Cotton Trail.

At the U.S. 90 intersection, I headed east towards the charming historic town of Monticello. Blooming crape myrtles lined the road and made for a highly scenic drive, although a much faster one. I passed nurseries and the vast Lake Miccosukee before entering Monticello and its antebellum homes and thriving downtown. Lunch was in order, so I stopped at one of the town’s excellent cafes, before continuing east.

Heading out of Greenville later that day, I wanted to continue my scenic driving journey. I headed south on County Road 275C, passed through the small rail town of Aucilla, and took a right on U.S. 27. I soon passed Robinson’s Pecan House near Lamont. There has been a yellow and orange pecan stand in that vicinity since I was a boy and I was glad to see the industry still thriving. I passed the abandoned tung oil factory in Capps before turning south onto W.W. Kelley Road at Chaires Crossroads. An immediate right put me on one of the area’s premier canopy roads, Old St. Augustine. This was part of the Old Spanish trail from Pensacola to St. Augustine and it wound past live oak and pine-covered pastoral lands. My tour ended when I reached Capital Circle and headed for home, but I felt richer for having taken some of the most scenic drives anywhere.

Click here for a map of Leon County’s designated canopy roads.          

Doug Alderson. Outdoor & Nature Expert from Tallahassee, FL Author:

Doug Alderson

Outdoor & Nature Expert


Doug Alderson is the author of several books, including Waters Less Traveled: Exploring Florida's Big Bend Coast (University Press of Florida 2005), The Vision Keepers: Walking for Native Americans and the Earth (Quest Books 2007), New Dawn for the Kissimmee River: Orlando to Okeechobee by Kayak (University Press of Florida, 2009), Encounters with Florida's Endangered Wildlife (University Press of Florida, 2010), and his newest book, Wild Florida Waters: Exploring the Sunshine State by Kayak and Canoe (Earthways Press, 2011). Additionally, his articles and photographs have been featured in magazines such as Sea Kayaker, Coast and Kayak, Wildlife Conservation, American Forests, Sierra, Mother Earth News and Shaman's Drum. He has won several state and national awards for his books and magazine features. Doug also works as the paddling trails coordinator for the Florida Office of Greenways and Trails.

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