About hiking in Dutchess County

Dutchess County, New York has 169 named trails tagged for hiking, covering 280 miles, an average of 1.7 miles each. The longest is Maybrook Trailway, at 15.0 miles. 14 run 5 miles or longer.

What the hiking trails in Dutchess County are like

By length, 114 are under a mile, 41 run 1 to 5 miles, and 14 are 5 miles or longer. 7 are loops, ending where they start; the longest is Overlook Trail, at 3.4 miles.

Of the 165 with measured elevation, Fishkill Ridge Trail climbs the most, about 4,142 ft, and 9 gain 1,000 ft or more.

All 169 hiking trails, longest first

Maybrook TrailwayHikeMTB15.0 mi Maybrook Trailway - hiking - Putnam Trailway to Hopewell JunctionHike15.0 mi Hudson Valley Greenway Trail (Pawling to Hopewell Junction)Hike14.9 mi Dutchess Rail TrailHikeMTB13.3 mi Red TrailHike13.3 mi Dutchess County Rail Trail - hiking - ESTHike13.2 mi Hudson Valley Greenway Trail (Hopewell Junction to Poughkeepsie)Hike13.0 mi Blue TrailHike9.6 mi Hudson Valley Greenway Trail (East Kingston to Tivoli)Hike8.5 mi Fishkill Ridge TrailHike8.4 mi Yellow TrailHike6.8 mi White TrailHike6.7 mi RedHike5.3 mi Fishkill Ridge Trail (White)Hike5.2 mi blueHike4.5 mi YellowHike4.2 mi Notch Trail (blue)Hike4.2 mi Wilkinson Memorial Trail (Yellow)Hike3.8 mi Overlook TrailHike3.4 mi Purple TrailHike3.3 mi OrangeHike3.0 mi Green TrailHike3.0 mi Newburgh, Dutchess and Connecticut RailroadHike3.0 mi Wappinger Green TrailHike2.6 mi Hyde Park TrailHike2.3 mi McKinney TrailHike2.2 mi Fishkill Creek Greenway & Heritage TrailHike2.1 mi Ridge TrailHike2.0 mi Furnace Pond LoopHike2.0 mi Casino TrailHike1.9 mi Casino Trail (Red)Hike1.9 mi Dennings Point TrailHike1.9 mi whiteHike1.9 mi Blue LoopHike1.9 mi Orange TrailHike1.8 mi Roosevelt Farm Lane TrailHike1.7 mi Poet's WalkHike1.6 mi GreenHike1.6 mi Hyde Park Train (Green)Hike1.6 mi Bard College Connector (Blue)Hike1.6 mi Yellow LoopHike1.5 mi Orange LoopHike1.3 mi Webster TrailHike1.2 mi Tivoli Commons Access (Blue) TrailHike1.2 mi Helen Johnson Woodworth Memorial Trail (red)Hike1.2 mi Wilkinson TrailHike1.2 mi Northside LineHikeMTB1.2 mi The Lane LoopHike1.2 mi North Bay (Blue) TrailHike1.1 mi Teaghpacksinck TrailHike1.1 mi Overlook (Red) TrailHike1.1 mi Appalachian Trail / Ridge TrailHike1.0 mi Top Cottage Trail (green)Hike1.0 mi Sierra Trail (Inner Loop)Hike1.0 mi Bluebird (Red) TrailHike1.0 mi Seirra Trail (Outer Loop)Hike1.0 mi Rudd Pond Trail (Red)Hike0.9 mi Nuclear Lake TrailHike0.9 mi Freedom Trail LoopHike0.9 mi Blue Buzzard TrailHike0.9 mi Klara Sauer TrailHike0.9 mi orange (snowmobile)Hike0.9 mi Wappinger Creek Greenway TrailHike0.9 mi Freedom TrailHike0.8 mi Walkway Over the HudsonHikeMTB0.8 mi Walkway over the Hudson - hikingHike0.8 mi Old Red trailHike0.8 mi yellow (woods road)Hike0.8 mi Dry Brook TrailHike0.8 mi Dry Brook Trail (Yellow)Hike0.8 mi Tower TrailHike0.8 mi Bridle PathHike0.8 mi Quercus Trail (green)Hike0.8 mi (um)Hike0.8 mi Penny RoadHike0.7 mi Breakneck Bypass TrailHike0.7 mi (red blazes)Hike0.7 mi (old yellow)Hike0.7 mi Lake TrailHike0.7 mi Tivoli Meadow TrailHike0.7 mi Collin's Trail (blue)Hike0.7 mi Hogback (Yellow) TrailHike0.7 mi hikingHike0.7 mi Quarry Hill TrailHike0.7 mi Powerline Trail (unmarked)HikeMTB0.7 mi Stream TrailHike0.6 mi Overlook (Blue) TrailHike0.6 mi Wappinger Creek Greenway Trail - North ExtensionHike0.6 mi tanHike0.6 mi Sawkill TrailHike0.6 mi Briggs TrailHike0.6 mi The Edgehill RoadHike0.5 mi PurpleHike0.5 mi Huntington Trail (red)Hike0.5 mi (yellow blazes)Hike0.5 mi Wright Trail (black)Hike0.5 mi Red Trail - Upper sectionHike0.5 mi Stone Church pathHike0.5 mi Drumlin Trail (yellow)Hike0.5 mi Outer LoopHike0.5 mi (orange?)Hike0.5 mi (bw)Hike0.5 mi Lime Kiln TrailHike0.5 mi North Trail (orange)Hike0.5 mi Hall-Christie TrailHike0.4 mi Red Wing Nature TrailHike0.4 mi Foghpacksinck TrailHike0.4 mi (magenta?)Hike0.4 mi Forest RunHike0.4 mi (blue blazes)Hike0.4 mi Appalachian Trail / Yellow LoopHike0.4 mi Hopeland Loop (blue)Hike0.4 mi Circle TrailHike0.4 mi The South Loop TrailHike0.4 mi LKTRHike0.3 mi Brace Mountain TrailHike0.3 mi Nimham TrailHike0.3 mi Nimham Trail (Green)Hike0.3 mi Arlington Sanitary Sewer Trail (1957)Hike0.3 mi Scout TrailHike0.3 mi Forest Trail (green)Hike0.3 mi The Ravine TrailHike0.3 mi The North RoadHike0.3 mi Chelsea Cove Drive SouthHike0.3 mi Swain Trail (blue)Hike0.3 mi Yellow Warbler TrailHike0.3 mi Hurd's Corner Entrance TrailHike0.3 mi Pink TrailHike0.3 mi East Tower TrailHike0.3 mi Ravine WalkHike0.3 mi Historic Roadbed TrailHike0.3 mi (blue + yellow blazes)Hike0.3 mi White + Green TrailHike0.3 mi Momakating TrailHike0.2 mi Red Trail (Hilltop)Hike0.2 mi Church TrailHike0.2 mi River RoadHike0.2 mi Inner LoopHike0.2 mi East Shore PathHike0.2 mi Iron Mine TrailHike0.2 mi North Ridge TrailHike0.2 mi Tivoli Commons SpurHike0.2 mi South Ridge TrailHike0.2 mi white + red trailsHike0.2 mi MagentaHike0.2 mi West Shore PathHike0.2 mi The Sunfish Cove TrailHike0.2 mi Red/OrangeHike0.2 mi (horrible)Hike0.2 mi orange + white + blue trailsHike0.2 mi The Saw Mill TrailHike0.2 mi Ridge Trail / Blue LoopHike0.2 mi Hook TrailHike0.2 mi Poughkeepsie and Eastern RailwayHike0.2 mi Beach PathHike0.2 mi North Pond TrailHike0.2 mi (white, horseshoe)Hike0.2 mi Emigh TrailHike0.2 mi The Cascade TrailHike0.1 mi South Pond TrailHike0.1 mi red + green trailsHike0.1 mi The Grade RoadHike0.1 mi The Lakeside RoadHike0.1 mi Hopeland TrailHike0.1 mi Davis TrailHike0.1 mi blue + white trailsHike0.1 mi Dave Miller Connector TrailHike0.1 mi Wappingers Creek Greenway TrailHike0.1 mi Breakneck Wilkinson Connector Trail (Green)Hike0.1 mi

← All Dutchess 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 4, 2026.