Atop a broad ridge overlooking a swath of forest protected by Eglin Air Force Base, Crestview is the county seat of Okaloosa County and lies between the western portal to Eglin and the eastern access to Blackwater River State Forest along the Florida Trail.
To connect these two popular hiking destinations, the trail’s present roadwalk route through this section passes right through the city’s historic downtown.
Crestview is located at the junction of U.S. 90, State Road 85 and Interstate Highway 10, which resulted in its being designated as the “Hub City” of northwest Florida .
The City of Crestview was officially incorporated in 1916. The name was chosen because of its location on the peak of a long woodland range between the Yellow and Shoal rivers. At an elevation of 235 feet above sea level, it is one of the highest points in the state. Also, it receives 65 inches of rainfall annually—the most in the State of Florida. The CSX, Inc. Railroad runs through Crestview and parallels the Old Spanish Trail which extends from Jacksonville west to El Paso, Texas. It is one of the great truck lines of the country, rich in tradition and history of the Indian, French, Spanish and English settlers. These early residents realized the natural advantages offered at this particular site for the building of a City and they set out to provide the foundation for such an undertaking. In 1997, Crestview was designated a Main Street Program by the Secretary of State.
Starting at the US 331 trailhead, hikers walk west into woods once a part of Choctawhatchee National Forest, established at the same time as the Ocala National Forest in 1908. But in 1940, the Forest became Eglin Air Force Base. Encompassing 724 square miles, the base protects the largest remaining old-growth longleaf pine forest in the United States, and with it, endangered creatures including the fox squirrel and red-cockaded woodpecker. Creeks cut into the clayhills, creating deep ravines lined with thickets of fragrant titi and seepage slopes sheltering rare colonies of pitcher plants. It’s an ideal spot for a long backpacking trip, with reliable water sources and pleasant primitive campsites with picnic tables and fire rings each night.
Where the trail emerges on SR 85 south of Crestview, it presents a disconnect in the corridor, where long-distance hikers follow the roadside blazes up to US 90 to reach the rest of the Eglin Trail on the western side of the base, paralleling the Yellow River. Work is actively underway to create more protected footpath in Eglin AFB to connect the two sections.
1. SR 85 Trailhead. Trailhead parking, registration kiosk. Trail turns right (north) and becomes roadwalk north on SR 85.
2. Bill Duggan Jr. Park. Restrooms, potable water, picnic tables, day use parking on the north shore of the Shoal River just south of services around I-10 at Crestview.
3. Milligan. Small convenience store at gas station along US 90.
4. Holt. Small town on US 90. Cozy Corner Café restaurant, Bowman’s Store with ATM, fried chicken. Former owners allowed camping behind store; ask permission. Brown’s Grocery to west.
5. Harold. The Harold Store has groceries with a picnic table and restrooms. It’s okay to park or camp at Harold Store, just ask owners first. Follow the orange blazes north from US 90 through the Hutton Unit to Deaton Bridge Road en route to Blackwater River State Park.
6. Deaton Bridge Trailhead. Day use parking is available for a fee. A white sand beach and swimming area are down a short trail to the right before the bridge. Cross the bridge over Blackwater River and turn left to follow blazes along riverbank. Blackwater River State Park is up the road 0.2 mile on the right. It has a campground and overnight parking available for a small fee.
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Atop a broad ridge overlooking a swath of forest protected by Eglin Air Force Base, Crestview is the county seat of Okaloosa County and lies between the western portal to Eglin and the eastern access to Blackwater River State Forest along the Florida Trail. 
Crestview - Grab & Go
The City of Crestview was officially incorporated in 1916. The name was chosen because of its location on the peak of a long woodland range between the Yellow and Shoal rivers. At an elevation of 235 feet above sea level, it is one of the highest points in the state. Also, it receives 65 inches of rainfall annually—the most in the State of Florida. 
Starting at the US 331 trailhead, hikers walk west into woods once a part of Choctawhatchee National Forest, established at the same time as the Ocala National Forest in 1908. But in 1940, the Forest became Eglin Air Force Base. Encompassing 724 square miles, the base protects the largest remaining old-growth longleaf pine forest in the United States, and with it, endangered creatures including the fox squirrel and red-cockaded woodpecker. Creeks cut into the clayhills, creating deep ravines lined with thickets of fragrant titi and seepage slopes sheltering rare colonies of pitcher plants. It’s an ideal spot for a long backpacking trip, with reliable water sources and pleasant primitive campsites with picnic tables and fire rings each night. 
Florida Trail Map Brochure