How many trails are near Winchester?

We list 91 trails within 30 miles of Winchester, Kentucky. This page shows the 60 closest.

What is the longest trail near Winchester?

Legacy Trail is the longest on this page at about 12 miles, 21 miles from Winchester.

Are there dog-friendly trails near Winchester?

Yes. Map data lists 2 trails on this page as open to dogs, including Cross Country Trail, Carnes Farm Trail. Most trails have no dog rule in our data yet, so check signs at the trailhead.

Trails near Winchester, KY

91 trails within 30 miles of Winchester, for hiking, biking, horseback riding and off-road riding. Tap a trail for its map, trailhead and directions.

Hiking trails (78) Walking trails (78) Bike trails (31) Mountain bike trails (17) Paved trails (36) Horse trails (21) ATV and UTV trails (30) Off-road and 4x4 trails (30) Dog-friendly trails (3) Greenways (3)

Quick picks

Closest: Winchester Walking Trail 0.8 mi, 1.4 mi away
Longest: Legacy Trail 12 mi, 21 mi away
Easy walk: John Holder Trail 1.2 mi, 7.1 mi away
Paved: Brighton Trail 3.4 mi, 13 mi away
Dog friendly: Cross Country Trail 0.9 mi, 19 mi away

All nearby trails

Winchester Walking Trail

1.4 mi away

0.8 mi long · Winchester

Hiking Biking Mountain biking

John Holder Trail

7.1 mi away

1.2 mi long · Winchester

Hiking

Hisle Farm Park

13 mi away

4.3 mi long · Lexington-Fayette

Hiking

Brighton Trail

13 mi away

3.4 mi long · Easy · Lexington-Fayette

Hiking Biking Paved

Upper Hines trail

13 mi away

1.1 mi long · Richmond

Hiking

Meadow Trail

14 mi away

1.3 mi long · Easy · Lexington

Hiking Paved

Blue Trail

14 mi away

0.7 mi long · Easy · Lexington

Hiking Paved

Red Loop Trail

14 mi away

3.8 mi long · Easy · Lexington

Hiking Paved

Orange Trail

14 mi away

1.0 mi long · Easy · Lexington

Hiking Paved

Freedom Trail

14 mi away

0.5 mi long · Easy · Lexington

Hiking Paved Wheelchair accessible

Pilot's Knob State Park Trail

14 mi away

1.1 mi long · Easy · Clay City

Hiking Paved

Green Trail

14 mi away

0.7 mi long · Easy · Lexington

Hiking Paved

Sage Point Trail

14 mi away

1.9 mi long · Easy · Clay City

Hiking Paved

Squires Road Bike Path

15 mi away

0.7 mi long · Easy · Lexington

Hiking Biking Paved

Squires Road Bike Path

15 mi away

0.5 mi long · Easy · Lexington

Hiking Biking Paved

Lansdowne-Merrick Park path

17 mi away

1.3 mi long · Lexington

Hiking Biking Mountain biking

Arboretum Walking Path

18 mi away

2.0 mi long · Easy · Mount Vernon

Hiking Paved

Fish Sticks

18 mi away

0.6 mi long · Easy · Lexington

Hiking Biking Mountain biking

Swamp Donkey

18 mi away

0.7 mi long · Easy · Lexington

Biking Mountain biking

Unpaved Arboretum Path

18 mi away

0.7 mi long · Easy · Mount Vernon

Hiking Paved

Upper Narrows

18 mi away

0.8 mi long · Easy · Lexington

Biking Mountain biking

Deer Run

18 mi away

1.1 mi long · Easy · Lexington

Biking Mountain biking

Arboretum Woods Trail

18 mi away

0.8 mi long · Easy · Mount Vernon

Hiking Paved

Lake Reba walking trail

18 mi away

0.7 mi long · Easy · Richmond

Hiking Paved

Jetstream

18 mi away

1.6 mi long · Easy · Lexington

Biking Mountain biking

Sloppy Flow

18 mi away

0.5 mi long · Easy · Lexington

Biking Mountain biking

Town Branch Commons Trail

18 mi away

1.6 mi long · Easy · Mount Vernon

Hiking Biking Paved

100 Proof

18 mi away

0.9 mi long · Moderate · Lexington

Biking Mountain biking

Legacy/Town Branch Connector

18 mi away

1.3 mi long · Easy · Mount Vernon

Hiking Biking Paved

Cross Country Trail

19 mi away

0.9 mi long · Dogs on leash · Richmond

Hiking Dogs allowed

Town Branch Trail

19 mi away

3.4 mi long · Easy · Mount Vernon

Hiking Biking Paved

Shillito Park Trail

20 mi away

2.3 mi long · Easy · Mount Vernon

Hiking Biking Paved

Carnes Farm Trail

20 mi away

3.0 mi long · Dogs on leash · Richmond

Dogs allowed

Tudor Farm Trail

20 mi away

1.4 mi long · Richmond

Hiking

Legacy Trail

21 mi away

12 mi long · Easy · Lexington-Fayette

Hiking Biking Paved

Riney B Trail

23 mi away

0.8 mi long · Easy · Nicholasville

Hiking Biking Paved

Fitness Trail

23 mi away

0.5 mi long · Easy · Nicholasville

Hiking Biking Paved

#1

24 mi away

1.2 mi long · Irvine

Hiking

#6

24 mi away

0.5 mi long · Irvine

Hiking

#2

24 mi away

0.6 mi long · Irvine

Hiking

Fort Jones Loop Trail

26 mi away

1.0 mi long · Camp Nelson National Monument

Hiking

Fort Jones Overlook Trail

26 mi away

1.1 mi long · Nicholasville

Hiking

Woodland Trail

26 mi away

1.1 mi long · Nicholasville

Hiking

Long Fort Trail

26 mi away

0.9 mi long · Camp Nelson National Monument

Hiking

Fort Putnam Loop Trail

26 mi away

0.6 mi long · Camp Nelson National Monument

Hiking

Meadow Trail

26 mi away

0.9 mi long · Nicholasville

Hiking

Barracks Loop Trail

26 mi away

0.4 mi long · Camp Nelson National Monument

Hiking

Fort Trail

27 mi away

0.5 mi long · Nicholasville

Hiking

Connector trail to Fort Putnam

27 mi away

0.2 mi long · Camp Nelson National Monument

Hiking

Depot Trail

27 mi away

0.5 mi long · Camp Nelson National Monument

Hiking

Walking Path

27 mi away

0.1 mi long · Easy · Camp Nelson National Monument

Hiking Paved

Monster Mash

27 mi away

0.6 mi long · Berea

Hiking Biking Mountain biking

Climb Time Trail (0.8mi)

27 mi away

0.8 mi long · Stanton

Hiking Biking Mountain biking

Tarzan

27 mi away

0.5 mi long · Berea

Hiking Biking Mountain biking

Jessamine Creek Gorge Preserve

28 mi away

1.2 mi long · Jessamine County

Hiking

Top Loop Trail (2mi)

28 mi away

1.9 mi long · Stanton

Hiking Biking Mountain biking

Great Crossing Walking Path

28 mi away

1.1 mi long · Easy · Georgetown

Hiking Biking Paved

POWDERMILL BRANCH

28 mi away

2.1 mi long · Daniel Boone National Forest

Cross Country Course

28 mi away

2.6 mi long · Easy · Wilmore

Hiking Paved

Hayride Trail

28 mi away

0.8 mi long · Versailles

Hiking

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Nearby cities

All trails in Kentucky

Common questions

How many trails are near Winchester?: We list 91 trails within 30 miles of Winchester, Kentucky. This page shows the 60 closest.
What is the longest trail near Winchester?: Legacy Trail is the longest on this page at about 12 miles, 21 miles from Winchester.
Are there dog-friendly trails near Winchester?: Yes. Map data lists 2 trails on this page as open to dogs, including Cross Country Trail, Carnes Farm Trail. Most trails have no dog rule in our data yet, so check signs at the trailhead.