Outbound Collective logo

Kentucky

Looking for the best chillin in Kentucky? We've got you covered with the top trails, trips, hiking, backpacking, camping and more around Kentucky. The detailed guides, photos, and reviews are all submitted by the Outbound community.

Top Chillin Spots in and near Kentucky

  • Pineville, Kentucky

    Explore the Lookout from Chained Rock

    5.0
    Located just north of the Cumberland Gap, Chained Rock is a local landform made unique by a long slung chain that comes with a tall tale of it's creation. According to legend the rock pinnacle overlooking the Cumberland River valley struck fear into the minds of young children, which was eased wi...
    Read more
  • Berea, Kentucky

    Hike the Pinnacles in Berea

    4.9
    6.59 mi / 1014 ft gain
    This is a trip with multiple sites to visit over the course of a day. Visiting all five would equal around 5 miles, or you can choose to only go to one, as there are some slightly strenuous hills. The most visited is the Main Lookout, and the West Pinnacle offers a little rock climbing. Between ...
    Read more
  • Stanton, Kentucky

    Hike to Courthouse Rock and Double Arch

    5.0
    6.1 mi
    Start at the trailhead located just past the Gray's Arch picnic area. Follow Auxier Ridge Trail #204 (white diamonds). You will pass a trail junction at 0.9 miles, but continue on Auxier Ridge. At the following fork in the trail keep right.Along the trail, you will catch views from the ridge of R...
    Read more
  • Slade, Kentucky

    Camp at Miguel's Pizza

    4.0
    The Red River Gorge is known for the best rock climbing in the east. A man named Miguel opened a pizzeria in the gorge, and soon began letting climbers camp behind the restaurant for a mere $2/night. Today, the tradition has continued, and dozens of climbers call Miguel's Pizza their climbing hom...
    Read more
  • West Point, Kentucky

    Hike to Tioga Falls

    4.7
    1.9 mi / 354 ft gain
    Recently the trail to Tioga Falls has re-opened even though they are still doing trail restoration. This is short little 1.9 mile out and back trail is perfect for the family and has one of the best waterfalls if you live anywhere near Louisville, Kentucky. Now while there is about 350 feet of el...
    Read more
  • Wilmore, Kentucky

    Hike to the Cave at Asbury Trails

    4.0
    1 mi / 430 ft gain
    The Asbury University trail system is located just south of Wilmore, KY along the lush emerald banks of the Kentucky River. Leisurely looping through the luscious limestone landmasses of the Kentucky bluegrass region, the trails at Asbury offer visitors an opportunity to obtain up-close understan...
    Read more
  • Henderson, Kentucky

    Hike the Wilderness Lake Trail

    3.0
    1 mi / 0 ft gain
    This well kept trail is one of seven trails at John James Audubon State Park. A great short hike for the family starts at roughly 600 ft with minimal elevation change. The trail is surrounded by hardwoods and moss for the first half mile then the forest opens up to a small lake/wetlands area. The...
    Read more
  • Gillmore, Kentucky

    Hike the Creation Falls and Rock Bridge Loop

    4.8
    1.38 mi / 285 ft gain
    From the Slade, KY exit take KY15 toward Campton to KY715 to Rock Bridge Rd.  Park at the Rock Bridge picnic area and take the trailhead closest to the entrance. The trailhead will quickly descend surrounding you with lush vegetation.  A rockshelter can be found on the right hand side of the tra...
    Read more
  • Beattyville, Kentucky

    Climb at the Motherlode in Red River Gorge

    1.2 mi
    These directions are similar to those marked in the Red River Gorge Climbing Guide. Be sure to pick one up at Miguel's Pizza or elsewhere to get a good idea of where all of the crags and climbing routes are. This adventure is to the Volunteer Wall and The Gallery crags.  The parking lot is marked...
    Read more
  • Parkers Lake, Kentucky

    Hike to Natural Arch in Daniel Boone National Forest

    1 mi / 300 ft gain
    Natural Arch is located in the Daniel Boone National Forest near the border of Tennessee and Kentucky. Once you get inside of the park there are many picnic tables and other areas to eat and sit and paths to walk on. The main attraction of the park however is the 100 foot wide arch that spans ove...
    Read more
  • Bowling Green, Kentucky

    Visit Lost River Cave

    4.5
    1.1 mi / 110 ft gain
    In the last 200 years, Lost River Cave has been used as a site for mills, a camp for Civil War soldiers, and a nightclub. Its history goes back many years before that—thousands in fact. Prehistoric nomadic Native American tribes used the cave for shelter and water as they hunted this valley. The ...
    Read more
  • Brandenburg, Kentucky

    Fly Fish Otter Creek Outdoor Recreation Area

    4.0
    First of all, it should be said that Otter Creek ORA is a great property offering far more than just fishing. There are campgrounds, hiking/horse trails, picnic areas, disc golf and more.  Although this adventure focuses on the fishing opportunities at Otter Creek, it's worth checking out no matt...
    Read more
  • Wellington, Kentucky

    Rock Climb Foxfire at the Red River Gorge

    Directions to Eagle Point Buttress from the Shell gas Station.Head west on KY-15 for 1.6 miles then turn left onto KY 77. Stay on KY-77 for 5.1 miles. While you are on this road you will go through a oneway tunnel so be careful of cars coming out from the other side. Once you cross a bridge over ...
    Read more
  • Mammoth Cave, Kentucky

    Hike to Sunset Point

    5.0
    0.3 mi / 0 ft gain
    This small hike is inside of the Mammoth Cave National Park is well know and provides a great place for small kids and is handicap accessible. The pathway itself is a flat boardwalk and is only about .3 of a mile. It features beautiful views of the mountains and lots of wildlife. The hike is also...
    Read more
  • Frankfort, Kentucky

    Hike through Cove Spring Park

    5.0
    1.5 mi / 249 ft gain
    At first glance, Cove Spring Park looks like any normal city park. In reality, it is a waterfall filled, 240 acres nature preserve hiding in plain site of Kentucky's capital city. The property is filled with wetlands, streams, springs, waterfalls, and historic structures that make this a great ge...
    Read more
  • McCreary County, Kentucky

    Photograph Cumberland Falls

    5.0
    The Cumberland Falls State Resort Park is home to several waterfalls, with the Cumberland Falls being the largest, most prominent, and most well known. It is also called the Niagara of the South due to its size and volume of water flow. It is famous for being the only place in the Western Hemisph...
    Read more