United States
›
Kentucky
›
Winchester

Best Hiking Trails near Winchester, Kentucky



link Copy Link
  • facebookFacebook
  • Twitter iconTwitter
  • emailEmail
directions Driving Directions

Seasonal Popularity

Overview

Explore hiking trails around Winchester, Kentucky. The best hike near Winchester is Indian Staircase via Sheltowee Trace National Recreation Trail and Bison Way Trail, 210, a 2.9 mile out and back trail in Daniel Boone National Forest.


  • Hiking Trails (160)
  • Parks & Forests (52)
  1. 1
    Indian Staircase via Sheltowee Trace National Recreation Trail and Bison Way Trail, 210
    ★ ★ ★ ★ ★ EASY 2.9 mi
  2. 2
    Creation Falls Loop via Rock Bridge Trail
    ★ ★ ★ ★ ★ EASY 2.3 mi
  3. 3
    Gray's Arch Loop via Rush Ridge FT 227
    ★ ★ ★ ★ ★ EASY 3.5 mi
  4. 4
    Hidden Arch Loop
    ★ ★ ★ ★ ★ EASY 2.2 mi
  5. 5
    Natural Bridge
    ★ ★ ★ ★ ★ EASY 1.7 mi
  6. 6
    Double Arch Loop
    ★ ★ ★ ★ ★ MODERATE 6.0 mi
  7. 7
    Raven Rock
    ★ ★ ★ ★ ★ EASY 3.4 mi
  8. 8
    Whittleton Arch via Sheltowee Trace Trail
    ★ ★ ★ ★ ★ EASY 2.2 mi
  9. 9
    Whittleton Arch Loop via Sheltowee Trace Trail
    ★ ★ ★ ★ ★ EASY 4.4 mi
  10. 10
    Chimney Top Rock Loop via Princess Arch Trail and Chimney Top Trail
    ★ ★ ★ ★ ★ EASY 1.3 mi

Daniel Boone National Forest Hiking Trails
Blue Ridge Parkway Hiking Trails
Shawnee State Forest Hiking Trails
Scott County Park Hiking Trails
Cove Spring Park Hiking Trails
Kincaid Lake State Park Hiking Trails
Cove Spring Park Hiking Trails
First Southern Veterans Park Hiking Trails
Fort Boonesborough State Park Hiking Trails
Isaac Murphy Memorial Art Garden Hiking Trails
Jim Beam Nature Preserve Hiking Trails
Jim Beam Nature Preserve Hiking Trails
Kentucky Horse Park Hiking Trails
Kincaid Lake State Park Hiking Trails
Life Adventure Center Hiking Trails
Marion County WMA and State Forest Hiking Trails
Ohio River Islands National Wildlife Refuge Hiking Trails
Old Fort Harrod State Park Hiking Trails
Owen County Park Hiking Trails
Perryville Battlefield State Park Hiking Trails
Piddle Park Hiking Trails
Scott County Park Hiking Trails
Shawnee State Forest Wilderness Area Hiking Trails
Webb Park Hiking Trails
Webb Park Hiking Trails
Webb Park Hiking Trails
Webb Park Hiking Trails
Whipple State Nature Preserve Hiking Trails
Woodford County Park Hiking Trails
Woodland Park Hiking Trails
  • Web App

    • Map
    • Find Trails
    • Upload
  • Resources

    • Hiking & Backpacking
    • Offroad
    • Hunting
    • Mountain Biking
    • Backcountry Skiing
    • Fishing
    • Map Catalog
    • Help & Forums
  • Purchase

    • Individuals
    • Professional
    • Outside+
    • Volunteer
    • Gifts
  • Company

    • Blog
    • Podcast
    • Jobs
    • Diversity
    • Partnerships
    • Media
  • Gaia GPS - Trail maps for every adventure

    Follow Us

    Download on the App Store Get it on Google Play

© Trailbehind Inc. - All Rights Reserved.

  Privacy • Terms

Outside Inc Logo

© 2022 Outside Interactive, Inc.

Outside Inc Logo