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Trails near Middletown, NY

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

Hiking trails (768) Walking trails (743) Bike trails (264) Mountain bike trails (213) Paved trails (101) Horse trails (137) ATV and UTV trails (3) Off-road and 4x4 trails (5) Dog-friendly trails (9) Snowmobile trails (5) Cross-country ski trails (6) Wheelchair-accessible trails (20) Rail trails (9) Greenways (3)

Quick picks

All nearby trails

Orange Heritage Trail Extension

0.1 mi away

3.1 mi long · Easy · Washington Heights

Hiking Biking Paved

The LYne (teal blazes)

1.5 mi away

2.5 mi long · Middletown

Hiking Biking Mountain biking

Red Trail

2.3 mi away

1.2 mi long · Middletown

Hiking

Blue Trail

2.6 mi away

1.2 mi long · Middletown

Hiking Biking Mountain biking

Orange Trail

2.8 mi away

0.6 mi long · Middletown

Hiking Biking Mountain biking

Highland Lakes - Inwood Road

4.4 mi away

1.3 mi long · Scotchtown

Hiking Horses

Highland Lakes - Red Trail

4.8 mi away

0.6 mi long · Scotchtown

Hiking Horses

Moonbeam O&W Railroad Bed East Trail

5.0 mi away

0.5 mi long · Easy · Washington Heights

Hiking Paved

Highland Lakes State Park

5.3 mi away

4.7 mi long · NY State Parks

Hiking Horses

Highland Lakes - Oak West

5.9 mi away

1.8 mi long · Scotchtown

Hiking Horses

Highland Lakes - Ice Trail

6.3 mi away

0.4 mi long · Scotchtown

Hiking Horses

Highland Lakes - Camp Orange

6.3 mi away

1.4 mi long · Scotchtown

Hiking Horses

Highland Lakes - Spano Road

6.3 mi away

1.1 mi long · Scotchtown

Hiking Horses

Highland Lakes - Green Trail

6.5 mi away

1.9 mi long · Scotchtown

Hiking Horses

Upper Ridge Trail

6.7 mi away

1.5 mi long · Scotchtown

Hiking

Orange Trail

6.7 mi away

0.6 mi long · Scotchtown

Hiking

Drunken Rich Trail

6.7 mi away

0.6 mi long · Scotchtown

Hiking

Highland Lakes - Red Trail 2

6.8 mi away

0.8 mi long · Scotchtown

Hiking Horses

Center Ridge Trail

7.1 mi away

0.8 mi long · Scotchtown

Hiking

Lower Ridge Trail

7.2 mi away

0.6 mi long · Scotchtown

Hiking

Graham Fire Tower Trail (Red)

7.8 mi away

0.9 mi long · Otisville

Hiking

O&W Rail Trail

7.9 mi away

1.9 mi long · Otisville

Hiking Rail trail

Ravine Trail (White)

8.1 mi away

1.1 mi long · Otisville

Hiking

D&H Canal Towpath Trail

8.4 mi away

3.2 mi long · Otisville

Hiking Biking Mountain biking

Old Railroad Trail

8.8 mi away

3.1 mi long · Pine Bush

Heritage Trail

9.3 mi away

0.6 mi long · Otisville

Hiking

Development Trail

9.5 mi away

2.4 mi long · Wurtsboro

Hiking

Red Trail

9.7 mi away

0.8 mi long · Otisville

Hiking

White Trail

9.7 mi away

0.7 mi long · Otisville

Hiking

Blue Trail

10 mi away

0.8 mi long · Otisville

Hiking

Wurtsboro Ridge State Forest Lower O&W Rail Trail

10 mi away

1.0 mi long · Easy · Wurtsboro

Hiking Biking Paved Rail trail

Mine Trail

10 mi away

0.8 mi long · Easy · Wurtsboro

Hiking Paved

White-Blazed Trail

11 mi away

1.5 mi long · Easy · Port Jervis

Hiking Paved

Ant Ramble Trail

11 mi away

1.1 mi long · Maybrook

Hiking Biking Mountain biking

Old Turnpike Trail

11 mi away

0.7 mi long · Wurtsboro

Hiking

Lenape Ridge Trail (Red)

11 mi away

2.1 mi long · Easy · Port Jervis

Hiking Paved

Marsh Trail

12 mi away

0.5 mi long · Chester

Hiking

Yrizarry Trail

12 mi away

0.6 mi long · Chester

Hiking

Ant Hill Trail

12 mi away

1.4 mi long · Maybrook

Hiking Biking Mountain biking

Stewart - Kellys Pond Trail

12 mi away

0.7 mi long · Maybrook

Hiking Horses

Beaver Pond Trail

12 mi away

1.0 mi long · Maybrook

Hiking Biking Mountain biking

Blue Trail

12 mi away

1.6 mi long · Otisville

Hiking

Wurtsboro Ridge State Forest Upper O&W Rail Trail

12 mi away

4.2 mi long · Easy · Wurtsboro

Hiking Paved Rail trail

D&H Canal Linear Park Towpath Trail

12 mi away

1.3 mi long · Easy · Dogs on leash · Wurtsboro

Hiking Biking Paved Wheelchair accessible Dogs allowed

Goose Pond Mountain Trail

12 mi away

2.9 mi long · Chester

Hiking

Winding Waters Trail

12 mi away

1.9 mi long · Eden

Hiking

Liberty Loop Trail

12 mi away

2.5 mi long · New York-New Jersey Trail Conference

Hiking

Drakes Trail

13 mi away

0.8 mi long · Maybrook

Hiking Biking Mountain biking

Rock Wall Trail

13 mi away

0.6 mi long · Maybrook

Hiking

Drakes Trail

13 mi away

1.1 mi long · Maybrook

Hiking Biking Mountain biking

Stewart - Stick Pond Trail

13 mi away

1.1 mi long · Easy · Maybrook

Biking Horses Paved

Red Trail

13 mi away

1.2 mi long · Rock Hill

Hiking

Pond Trail

13 mi away

0.7 mi long · Maybrook

Hiking Biking Mountain biking

Causeway

13 mi away

0.6 mi long · Maybrook

Hiking Biking Mountain biking

Fish Hatchery Trail (Red)

13 mi away

4.5 mi long · Rock Hill

Stewart - Windsor Trail

13 mi away

1.8 mi long · Maybrook

Hiking Biking Mountain biking Horses

Minisink Trail (Yellow)

13 mi away

1.8 mi long · Port Jervis

Hiking

Red Trail

13 mi away

3.6 mi long · Rock Hill

Hiking

V Notch Trail

13 mi away

0.9 mi long · Maybrook

Hiking Biking Mountain biking

Stewart - Horse Trail

13 mi away

0.8 mi long · Maybrook

Hiking Biking Mountain biking Horses

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Nearby cities

All trails in New York

Common questions

How many trails are near Middletown?
We list 801 trails within 30 miles of Middletown, New York. This page shows the 60 closest.
What is the longest trail near Middletown?
Highland Lakes State Park is the longest on this page at about 4.7 miles, 5.3 miles from Middletown.
Are there dog-friendly trails near Middletown?
Yes. Map data lists 1 trail on this page as open to dogs, including D&H Canal Linear Park Towpath Trail. Most trails have no dog rule in our data yet, so check signs at the trailhead.