Orange County Hiking Trails, NY | Trailmonger

340

Hiking

595 mi

Total length

About hiking in Orange County

Orange County, New York has 340 named trails tagged for hiking, covering 595 miles, an average of 1.7 miles each. The longest is Stillman Trail, at 17.3 miles. 29 run 5 miles or longer.

What the hiking trails in Orange County are like

By length, 179 are under a mile, 132 run 1 to 5 miles, and 29 are 5 miles or longer. 28 are loops, ending where they start; the longest is Sapphire Trail, at 8.6 miles.

Every one carries a difficulty rating: 144 easy, 180 moderate, and 16 hard. Of the 339 with measured elevation, Stillman Trail climbs the most, about 4,778 ft, and 38 gain 1,000 ft or more.

Hiking Trails — page 1 of 2

Stillman TrailHike17.3 mi Ramapo Dunderberg TrailHike14.3 mi Jessup TrailHike13.1 mi Long Path - Section 7Hike10.8 mi Scenic TrailHike10.3 mi Long Path - Section 6Hike9.5 mi Sapphire TrailHike8.6 mi Ramapo-Dunderberg TrailHike8.3 mi Orange Heritage TrailwayHikeMTB8.3 mi Winding Waters TrailHike7.7 mi West Valley TrailHike7.6 mi Long PathHike7.4 mi White Cross TrailHike7.2 mi Fire Tower TrailHike7.2 mi Bare Rock TrailHike7.1 mi Popolopen Gorge TrailHike7.0 mi Howell TrailHike6.8 mi Dunning TrailHike6.8 mi Victory TrailHike6.6 mi Red Back Hike TrailHike6.3 mi Nurian TrailHike6.3 mi Indian Hill LoopHike6.1 mi Doris Duke TrailHike6.0 mi Arden - Surebridge TrailHike5.8 mi Long Swamp TrailHike5.7 mi Red TrailHike5.7 mi 1779 TrailHike5.6 mi Sterling Ridge TrailHike5.5 mi White Bar TrailHike5.1 mi Arden-Surebridge TrailHike5.0 mi Wildcat Mountain TrailHike4.9 mi Anthony Wayne TrailHike4.4 mi 1777 W TrailHike4.3 mi Lake to Lake TrailHike4.3 mi Triangle TrailHike4.2 mi Otterkill TrailHike4.0 mi Lenape Ridge Trail (Red)Hike3.9 mi West Ridge TrailHike3.9 mi Western Ridge TrailHike3.9 mi McKeags Meadow TrailHike3.8 mi Barton Swamp TrailHike3.8 mi Silvermine RoadHike3.7 mi Allis TrailHike3.6 mi Outer LimitsHike3.6 mi Meadow LoopHike3.5 mi Townsend TrailHike3.5 mi Menomine TrailHike3.5 mi Old Railroad TrailHike3.4 mi Long Meadow ExtensionHike3.3 mi Seasonal Long PathHike3.2 mi Sterling Valley LoopHike3.1 mi Orange Heritage Trail ExtensionHikeMTB3.1 mi Shawangunk Ridge Trail / Long Path (Aqua)Hike3.1 mi Redback Hike Pink BlazeHike3.0 mi Sackett TrailHike3.0 mi Blue TrailHikeMTB3.0 mi Minisink Trail (Yellow)Hike3.0 mi Dejay Downs Trail (advanced)Hike3.0 mi Camp Orange RoadHike2.9 mi Goose Pond Mountain TrailHike2.9 mi Stillman Spring TrailHike2.8 mi Painted ApronHike2.7 mi Trestle TrailHike2.7 mi Lazy Hill RoadHike2.6 mi Conklin RoadHike2.5 mi Bluebird TrailHike2.4 mi Black Rock Hollow TrailHike2.3 mi White Oak TrailHike2.3 mi Scofield LaneHikeMTB2.2 mi Munsee Eagle NorthHikeMTB2.2 mi Walden-Walkill Rail TrailHikeMTB2.2 mi Shawangunk Ridge Trail (Blue)Hike2.2 mi Sterling Lake LoopHike2.2 mi Lost Bear Trail (intermediate)Hike2.2 mi Orange County Heritage TrailHikeMTB2.1 mi Island Pond RoadHikeMTB2.1 mi Appalachian Trail;Ramapo-Dunderberg TrailHike2.1 mi Bypass TrailHikeMTB2.0 mi D&H Canal TowpathHike2.0 mi Bockey Swamp TrailHike2.0 mi Drakes TrailHikeMTB2.0 mi Bottle Cap TrailHike2.0 mi Bottlecap TrailHike2.0 mi Green TrailHike1.9 mi Brooks Pond TrailHike1.9 mi O&W Rail TrailHike1.9 mi McKeags MeadowHike1.9 mi Fire Tower Connector TrailHike1.9 mi Blueberry KarmaHike1.8 mi Oak Road WestHike1.8 mi Ramapo-Dunderberg/Appalachian TrailHike1.8 mi Sweet Clover TrailHike1.8 mi Hutchinson TrailHikeMTB1.8 mi Appalachian Trail ConnectorHike1.8 mi Windsor TrailHikeMTB1.8 mi Escarpment TrailHikeMTB1.7 mi Schunnemunk Meadows TrailHike1.7 mi White TrailHike1.7 mi FlintlockHike1.7 mi Lichen TrailHike1.7 mi Orange TrailHikeMTB1.6 mi Sweet CloverHike1.6 mi Furnace LoopHike1.6 mi Highland Lake RoadHikeMTB1.6 mi Major Welch TrailHike1.6 mi Walt's Keep Trail (moderate)Hike1.6 mi OrangeHike1.6 mi Scout's Honor Trail (intermediate)Hike1.5 mi Old West Point RoadHike1.5 mi Dark HollowHike1.5 mi Dark Hollow TrailHike1.5 mi Timp-Torne TrailHike1.5 mi Upper Ridge TrailHike1.5 mi White-Blazed TrailHike1.5 mi Chatfield TrailHike1.5 mi Hickory Hollow RoadHikeMTB1.5 mi Compartment TrailHike1.5 mi Parker Cabin HollowHike1.5 mi Bobcat TrailHike1.5 mi Lange Farm TrailHikeMTB1.5 mi Ant Hill TrailHikeMTB1.4 mi Pochuck Mountain TrailHike1.4 mi Hogback Mountain TrailHike1.4 mi Appalachian Trail;Highlands TrailHike1.4 mi Parker Cabin Hollow TrailHike1.4 mi Continental RoadHike1.4 mi Honey Hill TrailHike1.4 mi Old ATV TrailHike1.4 mi Power Line TrailHikeMTB1.4 mi Popologen Gorge TrailHike1.4 mi Tufted Trail (moderate)Hike1.3 mi Hulse RoadHike1.3 mi Pine Meadow TrailHike1.3 mi Pine Meadown TrailHike1.3 mi Inwood RoadHike1.3 mi Red BackHike1.3 mi Juda Hunter Trail (intermediate)Hike1.3 mi Arthur TrailHike1.3 mi Carpenter RoadHike1.3 mi DawnHikeMTB1.3 mi Tower Vue TrailHike1.3 mi Nawahunta Fire RoadHike1.2 mi Towpath Trail (advanced)Hike1.2 mi Reservoir Road Trail (moderate)Hike1.2 mi Lenni Lenape Trail (moderate)Hike1.2 mi Unmarked Dirt TrailHike1.2 mi Pittman RobertsonHikeMTB1.2 mi Blue Disc TrailHike1.2 mi Ant Ramble TrailHikeMTB1.1 mi Surebridge Swamp RoadHike1.1 mi Spano RoadHike1.1 mi Appalachian Trail;1779 TrailHike1.1 mi Ravine Trail (White)Hike1.1 mi White Cloud TrailHike1.0 mi Munsee EageHikeMTB1.0 mi Beaver Pond TrailHike1.0 mi Fire Tower Trail / West Valley TrailHike1.0 mi McKeon Loop TrailHike1.0 mi Turntable Trail (advanced)Hike1.0 mi Sugaree Trail (intermediate)Hike1.0 mi Augusta Mine TrailHike1.0 mi Munsee Eagle SouthHikeMTB1.0 mi CampHikeMTB1.0 mi Ridge to Ridge TrailHike1.0 mi Hurst TrailHike1.0 mi Wedgewood DriveHike1.0 mi D & H Canal & Gravity Railroad Heritage Corridor - Port Jervis Branch TrailHike1.0 mi Red Back SouthHike0.9 mi Armstrong Lane TrailHike0.9 mi White Oak RoadHike0.9 mi McKeags Meadow ConnectorHike0.9 mi Skyline Path (moderate)Hike0.9 mi Old Arden RoadHikeMTB0.9 mi Unmarked TrailHike0.9 mi Pine Swamp RoadHike0.9 mi Pufftown RoadHike0.9 mi Redback SouthHike0.9 mi Oak RoadHike0.9 mi Lakeville Ironworks TrailHike0.9 mi Graham Fire Tower Trail (Red)Hike0.9 mi Delaware Trail (easy)Hike0.9 mi Hasenclever Mountain TrailHike0.9 mi BearHikeMTB0.9 mi V Notch TrailHikeMTB0.9 mi Sara's WayHikeMTB0.9 mi Tuxedo-Mount Ivy TrailHike0.9 mi Summer Hill RoadHike0.8 mi Warbler TrailHike0.8 mi GreenHike0.8 mi Butter Hill TrailHike0.8 mi Arden-Surebridge Trail / Long PathHike0.8 mi Tallulah Trail (intermediate)Hike0.8 mi Duggan TrailHike0.8 mi Center Ridge TrailHike0.8 mi Indian Hill TrailHike0.8 mi Starcrawf Trail (moderate)Hike0.8 mi Nat Stillman TrailHike0.8 mi Moranigan ExtensionHike0.8 mi Horse TrailHikeMTB0.8 mi Campsite Trail (moderate)Hike0.8 mi Stahahe Brook TrailHike0.8 mi DukesHike0.8 mi Cosmic CharlieHike0.7 mi H. Peter Stern TralHike0.7 mi Orchard TrailHike0.7 mi Resevoir TrailHike0.7 mi Village Vista TrailHike0.7 mi Reservoir TrailHike0.7 mi Ramapo-Dunderberg-Tuxedo-Mount Ivy TrailHike0.7 mi Pond TrailHikeMTB0.7 mi Colden TrailHikeMTB0.7 mi RedbackHike0.7 mi Bog Meadow RoadHike0.7 mi Holography Trail (moderate)Hike0.7 mi Pine View Trail (easy)Hike0.7 mi 5 BridgesHike0.7 mi Cranberry Mine TrailHike0.6 mi Poult's Attack Trail (advanced)Hike0.6 mi Beginner's Berm Trail (easy)Hike0.6 mi Rock Wall TrailHike0.6 mi Pine RootHikeMTB0.6 mi Brant Path (easy)Hike0.6 mi Huguenot HillHike0.6 mi Heritage TrailHike0.6 mi Pine Meadow ConnectorHike0.6 mi Highalnds TrailHike0.6 mi Pecks RoadHike0.6 mi Hill of Pines TrailHike0.6 mi SaratogaHike0.6 mi Meadow View TrailHikeMTB0.6 mi Fire Tower / Highlands / Sterling Ridge TrailHike0.6 mi CausewayHikeMTB0.6 mi Mahackamacck Trail (moderate)Hike0.6 mi Yrizarry TrailHike0.6 mi Price Check Trail (advanced)Hike0.6 mi Lower Ridge TrailHike0.6 mi Island Pond TrailHike0.6 mi Drunken Rich TrailHike0.6 mi Sibyl's PathHike0.5 mi Moonbeam O&W Railroad Bed East TrailHike0.5 mi Swamp TrailHike0.5 mi Brook TrailHike0.5 mi North Shore RoadHikeMTB0.5 mi Marsh TrailHike0.5 mi Stahahe High Peak TrailHike0.5 mi Flirtation WalkHike0.5 mi Maple AlleeHike0.5 mi McKeags Meadow / Red BackHike0.5 mi Appalachian Trail;Anthony Wayne TrailHike0.5 mi Out N Back Path (moderate)Hike0.5 mi Moranigan Trail (intermediate)Hike0.5 mi Long TrailHike0.5 mi Snowmobile TrailHike0.5 mi Big Trees TrailHikeMTB0.5 mi Bryan's WayHikeMTB0.5 mi BlueHike0.5 mi Louis V. Mills Memorial Trail (White)Hike0.5 mi Hogback ConnectorHike0.5 mi Giant Steps TrailHikeMTB0.5 mi Lake SkenontoTrailHike0.5 mi Juda HunterHike0.4 mi FiestaHikeMTB0.4 mi Hula Hubbard Trail (intermediate)Hike0.4 mi Eagle Lake TrailHike0.4 mi hikingHike0.4 mi Appalachian Trail;Timp-Torne TrailHike0.4 mi Ice TrailHike0.4 mi Crooked RoadHike0.4 mi Ohanzee Trail (moderate)Hike0.4 mi Sterling Mine Rd Bypass TrailHike0.4 mi Hudson WalkHike0.4 mi Michael W. McCarthy Memorial Riverside WalkwayHike0.4 mi Cactus TrailHikeMTB0.4 mi Townsend Trail / Wildcat Mountain TrailHike0.4 mi Eagle Valley Rd Bypass TrailHike0.4 mi Clove Furnace DriveHikeMTB0.4 mi Southfields Branch RailwayHike0.4 mi Kellys Pond TrailHike0.4 mi Twin Forts TrailHike0.3 mi Out N BackHike0.3 mi Short TrailHike0.3 mi Bull Mine TrailHike0.3 mi Lake Skemonto TrailHikeMTB0.3 mi Chester Commons Hiking TrailHike0.3 mi Unmaintained dirt roadHike0.3 mi Yellow TrailHike0.3 mi Moonbeam O&W Railroad Bed WestTrailHike0.3 mi Lake Tiorati TrailHike0.3 mi Middle EarthHikeMTB0.3 mi Broken Ties Path (moderate)Hike0.3 mi MuskratHikeMTB0.3 mi Pond ExtensionHikeMTB0.3 mi Megaliths TrailHike0.3 mi PrimeHikeMTB0.3 mi (new tail) Pink RibbonHike0.3 mi Narrows Trail (moderate)Hike0.3 mi Ledge TrailHike0.3 mi ShieldsHikeMTB0.2 mi Rut TrailHike0.2 mi White Bar/Dunning TrailHike0.2 mi

← All Orange County trails

Trail geometry from OpenStreetMap contributors, licensed ODbL. Elevation from the USGS 3D Elevation Program. Compiled and published by Trailmonger · trail data last rebuilt October 25, 2026.