Kentucky Trail Town

The trail system currently consists of two color coded trails which start on Tygart St. in downtown Olive Hill between the Historic Railroad Depot Trailhead and Tygart Creek.  The trails are all designed to move you from downtown into the surrounding countryside in no more than 10 or 15 minutes.  The existing trails use low traffic city streets and country roads to move you to many locations which provide access to the rugged and beautiful backcountry surrounding Olive Hill.  

If you are an equestrian looking for a guided ride in our area, please check the events calendar (“Events” tab) on this site.  There are rides happening almost every weekend, weather permitting, and most are open to the public.   

We are working on connecting many more unpaved backcountry roads to our system–several of them will be long distances across country trails.  In the meantime, we appreciate your patience with so much asphalt!

trail map
Tap or click for map

Green Trail (8.3 miles)

The Green Trail connects Olive Hill to the beautiful trail system at Carter Caves State Resort Park.  It begins at the Depot Trailhead, Tygart St., downtown Olive Hill.  This trail utilizes mostly asphalt road to the state property line near the park.  Trail is marked in color on the road.

Traveler can see a beautiful view from Blueberry Ridge, and once on 1025 and on Prater & James Chapel roads, can enjoy lush, green rolling hills.  On James Chapel Road, there is a wide shoulder that can be used as trail, as an alternative to asphalt.  There is an old one-room schoolhouse on the right soon after turning onto James Chapel.  At the end of James Chapel Road, the trail user will move onto dirt trail at the state property line, at the 8.3 mile marker.  This begins a connector trail, also marked “green”, which is approximately one mile long and takes the trail user to the Carter Caves Kiser Hollow Trail.

The park has interesting and beautiful points of geologic interest, such as caves and natural arches, and 15 miles of multi-use (non-motorized) trails, plus another 15 miles of foot trails, within the park proper & the surrounding state forest.  Check out the horse campground, and great food at the lodge.  Additional trail information can be obtained at the lodge, including directions for leaving the park to connect with Sand Ridge – a trail that involves a high point with breathtaking views (warning:  not for those with fear of heights)– which drops the traveler right into Carter City close to the entrance to Lazy Gait Horse Camp.

DIFFICULTY: The green trail is primarily “easy” with short sections of “moderate” due to steep grade.  Surface is smooth asphalt except for one short (approx ½ mi.) section of rugged gravel all the way to the state property line.  Once inside the state property, trails are packed soil with some sections of narrow, rocky travel, which warrant a rating of “difficult.”

Green Alternate Trail/Broken Green (13 miles)

Connects downtown Olive Hill with Carter Caves State Resort Park, and is indicated by broken green line markings on the road.  This trail utilizes asphalt roadways for the entire trail, and is appropriate not only for road-only bicycles, but for motorists looking for a scenic route to Carter Caves.  This trail also leads any interested traveler to points of historic interest.

This trail begins at the Depot Trailhead, takes the trail user up Railroad St., onto US 60, then to the intersection at 1025.  At 1025, Green Alternate Trail converges with the Green Trail, then diverges at the intersection at Prater Road.  1025 has beautiful country scenery, with rolling hills and a view of a working chestnut tree farm along the way.  Where Green and Green Alternate diverge, Green Alternate continues on 1025.  Further down, the trail turns onto Oakland Ridge.  On this section, the traveler will move through a portion of lush state forest, coming out at the top of Oakland Ridge at the point where a beautiful vista of hills and open countryside can be enjoyed.  At the end of Oakland Ridge road, the trail user will turn right onto KY 182 and follow it to the entrance of Carter Caves.

Kentucky history enthusiasts can visit the gravesite of Gov.William Fields, as well as the site of his home, by using Green Alternate.    From the point where you turn right off Railroad St. and onto US 60, you will travel .5m.  On the right, you will see the entrance to the JOUAM & Eagle Cemetery – Gov. Fields’ grave is in the section closest to US 60.  After this stop, get back on Green Alternate and travel east to the left turn onto 1025.  Those interested in seeing Gov. Fields’ homesite can pass the 1025 turnoff and travel approximately .25m on US 60.  The site is on the right – there is a historical marker.  As another point of interest, just beyond the Fields’ homesite is Fields Bridge, the only arched bridge in KY Highway District Nine.  There is a public access watercraft launch on the west end of the bridge.

DIFFICULTY: For road biking, the difficulty level would be “difficult” due to steep grade.

Red Trail (10 miles)

Follow the Red Trail markings from the trailhead for a loop which finishes back at your starting point. It involves paved road up to the City Lake property, and dirt trail within the lake area. The Red Trail proper provides an intermediate level ride. Side trails within the City Lake area are more advanced and may be of interest to off-road cyclists. Points of interests along the way include the site of the General Refractories Brickyard which was once the largest fire brick manufacturing location in the world, and portions of the Midland Trail (a pioneer roadway which connected St. Louis to Washington D.C. and points in between). The trail passes through the Clay farm and the old Qualls Homesite and has side trails which take you to numerous trails around Olive Hill City Lake. Take time to explore this area. The Red Trail continues through scenic Ranch Road and Blueberry Ridge (beautiful views) and down Mills Branch to bring you back to your starting point. Ranch Road, Blueberry Ridge and Mills Branch are paved.

Tygart Creek (14 miles)

Tygarts Creek provides a beautiful and sometimes challenging canoe/ kayak voyage through the Tygarts Creek Gorge.  There are two public accesses:  1) next to the Tygart Creek bridge in front of the trailhead in downtown Olive Hill, and 2)  at the west end of Fields Bridge, behind the Tackett home (site of the Governor Fields home) at 115 Ridge Rd., Olive Hill.  Tygarts will take you to the entrance of Carter Caves State Resort Park– approximately an eight-hour trip.  The journey showcases gorgeous and interesting views of land formation, such as natural palisades.  For more information, go to, and for water levels, visit

DIFFICULTY: Easy to Difficult depending on water level; can be ‘extreme’ in high water.