How many trails are near Crestwood?

We list 442 trails within 30 miles of Crestwood, Illinois. This page shows the 60 closest.

What is the longest trail near Crestwood?

OBT-5 is the longest on this page at about 36 miles, 7.5 miles from Crestwood.

Are there dog-friendly trails near Crestwood?

Yes. Map data lists 1 trail on this page as open to dogs, including Orland System Red Trail. Most trails have no dog rule in our data yet, so check signs at the trailhead.

Trails near Crestwood, IL

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

Hiking trails (368) Walking trails (348) Bike trails (349) Mountain bike trails (120) Paved trails (253) Horse trails (55) Dog-friendly trails (9) Snowmobile trails (4) Cross-country ski trails (37) Wheelchair-accessible trails (12) Greenways (15)

Quick picks

Closest: Midlothian Meadows Trail System 2.9 mi, 2.4 mi away
Longest: OBT-5 36 mi, 7.5 mi away
Easy walk: Midlothian Meadows Trail System 2.9 mi, 2.4 mi away
Paved: Midlothian Meadows Trail System 2.9 mi, 2.4 mi away
Dog friendly: Orland System Red Trail 5.0 mi, 7.1 mi away
Mountain biking: Orland Park Greenway 3.1 mi, 4.1 mi away
Horseback riding: Yellow Loop 8.1 mi, 5.8 mi away

All nearby trails

Midlothian Meadows Trail System

2.4 mi away

2.9 mi long · Easy · Forest Preserve District of Cook County

Hiking Biking Paved

Tinley Creek Red Loop

2.8 mi away

9.3 mi long · Easy · Forest Preserve District of Cook County

Hiking Biking Paved

Tinley Creek Orange Paved Trail

3.1 mi away

0.5 mi long · Easy · Forest Preserve District of Cook County

Hiking Biking Paved

Tinley Creek Black Paved Trail

3.1 mi away

1.1 mi long · Easy · Forest Preserve District of Cook County

Hiking Biking Paved

Oak Forest Heritage Preserve Trail System

3.4 mi away

2.2 mi long · Easy · Forest Preserve District of Cook County

Hiking Biking Paved

Tinley Creek Green Trail

3.4 mi away

2.2 mi long · Easy · Forest Preserve District of Cook County

Hiking Biking Paved

Tinley Creek Purple Paved Trail

3.4 mi away

2.6 mi long · Easy · Forest Preserve District of Cook County

Hiking Biking Paved

Fieldcrest Drive Path

3.7 mi away

1.0 mi long · Easy · Oak Forest

Hiking Biking Paved

Tinley Creek Yellow Paved Trail

3.8 mi away

0.7 mi long · Easy · Forest Preserve District of Cook County

Hiking Biking Paved

Tinley Creek Blue Paved Trail

3.9 mi away

2.9 mi long · Easy · Forest Preserve District of Cook County

Hiking Biking Paved

Tinley Creek Yellow Unpaved Trail

3.9 mi away

1.2 mi long · Forest Preserve District of Cook County

Hiking

Tinley Creek Green Paved Trail

3.9 mi away

0.5 mi long · Forest Preserve District of Cook County

Hiking Biking Mountain biking

Palos Heights Bicycle Path

4.0 mi away

2.2 mi long · Easy · Forest Preserve District of Cook County

Hiking Biking Paved

Orland Park Greenway

4.1 mi away

3.1 mi long · Orland Park

Hiking Biking Mountain biking Greenway

80th Avenue

4.2 mi away

0.8 mi long · Orland Hills

Hiking Biking Mountain biking

151st Street

4.4 mi away

0.4 mi long · Orland Park

Hiking Biking Mountain biking

Kickapoo Woods Red Paved Loop Trail

5.2 mi away

1.0 mi long · Easy · Forest Preserve District of Cook County

Hiking Biking Paved

Yellow Loop

5.8 mi away

8.1 mi long · Forest Preserve District of Cook County

Hiking Horses

Purple Trail

5.8 mi away

0.4 mi long · Forest Preserve District of Cook County

Hiking

LaGrange Road

5.9 mi away

1.6 mi long · Easy · Orland Park

Hiking Biking Paved

Green Unpaved Trail

6.0 mi away

0.4 mi long · Forest Preserve District of Cook County

Hiking

Humphrey Bike Trail

6.0 mi away

3.1 mi long · Orland Park

Hiking Biking Mountain biking

Brown Trail

6.4 mi away

0.4 mi long · Forest Preserve District of Cook County

Hiking

88th Avenue Trail

6.5 mi away

1.5 mi long · Orland Hills

Hiking Biking Mountain biking

Sag Valley Trail System

6.9 mi away

12 mi long · Easy · Forest Preserve District of Cook County

Hiking Biking Paved

Black Trail

6.9 mi away

0.8 mi long · Forest Preserve District of Cook County

Hiking

167th Street Trail

7.0 mi away

0.5 mi long · Orland Hills

Hiking Biking Mountain biking

Orland System Red Trail

7.1 mi away

5.0 mi long · Easy · Dogs allowed · Forest Preserve District of Cook County

Hiking Biking Paved Dogs allowed

Yellow Primitive Loop

7.1 mi away

1.2 mi long · Easy · No dogs · Forest Preserve District of Cook County

Hiking Biking Paved

Orange Primitive Trail

7.2 mi away

1.2 mi long · Easy · Forest Preserve District of Cook County

Hiking Biking Paved

Vollmer Road Grove Trail System

7.2 mi away

4.0 mi long · Easy · Forest Preserve District of Cook County

Hiking Biking Paved

LaGrange Road Trail

7.3 mi away

1.4 mi long · Orland Hills

Hiking Biking Mountain biking

Tan Trail

7.3 mi away

2.5 mi long · Easy · Forest Preserve District of Cook County

Hiking Biking Paved

Dan Ryan Black Paved Loop Trail

7.4 mi away

0.9 mi long · Easy · Forest Preserve District of Cook County

Hiking Biking Paved

Tan Trail

7.5 mi away

0.5 mi long · Forest Preserve District of Cook County

Hiking

Palos Trail System

7.5 mi away

7.0 mi long · Easy · Forest Preserve District of Cook County

Hiking Biking Paved

OBT-5

7.5 mi away

36 mi long · Easy · Outerbelt Alliance NFP

Hiking Biking Paved

Blue South Single Track

7.5 mi away

3.0 mi long · Forest Preserve District of Cook County

Hiking Biking Mountain biking Horses

Lorado Taft Trail

7.5 mi away

1.5 mi long · Forest Preserve District of Cook County

Red Single Track Trail

7.5 mi away

1.7 mi long · Forest Preserve District of Cook County

Hiking Biking Mountain biking Horses

Major Taylor Bicycle Trail

7.5 mi away

8.4 mi long · Easy · City of Chicago

Hiking Biking Paved

Purple East Unpaved Spur

7.7 mi away

0.2 mi long · Moderate · Forest Preserve District of Cook County

Hiking Biking Horses Paved

Orange Unpaved Trail

7.7 mi away

1.1 mi long · Easy · Forest Preserve District of Cook County

Hiking Biking Paved

104th Avenue

7.8 mi away

0.5 mi long · Orland Hills

Hiking Biking Mountain biking

Purple Primitive Trail

7.9 mi away

0.6 mi long · Easy · Forest Preserve District of Cook County

Hiking Biking Paved

White Oak Trail

8.1 mi away

0.8 mi long · Easy · Forest Preserve District of Cook County

Hiking Paved

Farm Pond Trail

8.1 mi away

0.6 mi long · Easy · Forest Preserve District of Cook County

Hiking Paved

Brown Primitive Loop

8.2 mi away

1.2 mi long · Easy · Forest Preserve District of Cook County

Hiking Biking Paved

Green East Single Track

8.3 mi away

0.6 mi long · Forest Preserve District of Cook County

Hiking Biking Mountain biking Horses

Tan West Single Track

8.3 mi away

1.6 mi long · Forest Preserve District of Cook County

Hiking

Tan Primitive Trail

8.4 mi away

1.0 mi long · Easy · Forest Preserve District of Cook County

Hiking Paved

Black Oak Trail

8.4 mi away

1.2 mi long · Easy · Forest Preserve District of Cook County

Hiking Paved

Brown East Trail

8.6 mi away

3.8 mi long · Moderate · Forest Preserve District of Cook County

Hiking Biking Horses Paved

Blue Trail

8.7 mi away

0.9 mi long · Easy · Forest Preserve District of Cook County

Hiking Biking Mountain biking Horses

Olympia Fields Path System

8.7 mi away

2.1 mi long · Flossmoor

Hiking Biking Mountain biking

Crawford Avenue

8.7 mi away

0.5 mi long · Matteson

Hiking Biking Mountain biking

Yellow Paved Loop

8.7 mi away

1.6 mi long · Easy · Forest Preserve District of Cook County

Hiking Biking Paved

Black Unpaved Trail

8.7 mi away

4.0 mi long · Hard · Forest Preserve District of Cook County

Hiking Biking Mountain biking Horses

Saint Francis Road

8.7 mi away

2.4 mi long · Easy · Frankfort Square

Biking Paved

Brown Paved Trail

8.7 mi away

0.4 mi long · Easy · Forest Preserve District of Cook County

Hiking Biking Paved

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All trails in Illinois

Common questions

How many trails are near Crestwood?: We list 442 trails within 30 miles of Crestwood, Illinois. This page shows the 60 closest.
What is the longest trail near Crestwood?: OBT-5 is the longest on this page at about 36 miles, 7.5 miles from Crestwood.
Are there dog-friendly trails near Crestwood?: Yes. Map data lists 1 trail on this page as open to dogs, including Orland System Red Trail. Most trails have no dog rule in our data yet, so check signs at the trailhead.