About hiking in Western Connecticut Planning Region

Western Connecticut Planning Region, Connecticut has 246 named trails tagged for hiking, covering 396 miles, an average of 1.6 miles each. The longest is hiking, at 117 miles. 11 run 5 miles or longer.

What the hiking trails in Western Connecticut Planning Region are like

By length, 180 are under a mile, 55 run 1 to 5 miles, and 11 are 5 miles or longer. 42 are loops, ending where they start; the longest is Hardwood Trail, at 4.8 miles.

Every one carries a difficulty rating: 113 easy, 130 moderate, and 3 hard. Of the 245 with measured elevation, hiking climbs the most, about 12,546 ft, and 10 gain 1,000 ft or more.

All 246 hiking trails, longest first

hikingHike117 mi Norwalk River Valley TrailHikeMTB16.4 mi Ives Trail GreenwayHike13.4 mi Zoar TrailHike12.7 mi Al's TrailHike10.0 mi Saugatuck TrailHike9.5 mi Deer Pond Farm TrailsHike6.7 mi Godfrey TrailHike6.4 mi Housatonic Range TrailHike5.8 mi Aspetuck Valley TrailHike5.7 mi Lillinoah TrailHike5.6 mi Hardwood TrailHike4.8 mi Red TrailHikeMTB4.7 mi BlueHikeMTB4.6 mi Yellow LoopHike4.4 mi Troop 7 TrailHike4.1 mi Green TrailHikeMTB3.8 mi Pillars TrailHike3.7 mi White TrailHikeMTB3.5 mi Stephenson TrailHike3.4 mi Hiltebeitel TrailHike3.2 mi Bedford TrailHike3.1 mi Yellow TrailHikeMTB3.0 mi Two Ridges TrailHike3.0 mi Cedar Cliff TrailHike2.7 mi Green LoopHike2.6 mi Bruzelius TrailHike2.5 mi Ridgefield Rail TrailHike2.3 mi Aspetuck TrailHike2.2 mi Pond TrailHike2.1 mi Firehouse TrailHike2.0 mi Burn TrailHike2.0 mi Orange TrailHike2.0 mi WhiteHikeMTB2.0 mi Sap Brook TrailHike1.9 mi McCormack Blue TrailHike1.9 mi Oak TrailHikeMTB1.9 mi Blue TrailHike1.8 mi Sega Meadows Foot PathHike1.8 mi McCormack White TrailHike1.8 mi Munro TrailHike1.7 mi Joan's TrailHike1.6 mi Ridegfield High School Cross Country TrailHike1.6 mi Knapp WayHike1.6 mi Ives Trail Greenway AlternativeHike1.5 mi Perry TrailHike1.4 mi Falls TrailHike1.4 mi Laurel TrailHike1.4 mi Old FieldHike1.3 mi Gneiss TrailHike1.3 mi The DriftwayHike1.3 mi Lake TrailHike1.3 mi Riverbottom RoadHike1.3 mi Delia TrailHike1.2 mi RedHikeMTB1.2 mi Black Birch TrailHike1.2 mi Main RoadHike1.2 mi Ensor's TerraceHike1.1 mi Power Line TrailHike1.1 mi Inner RoadHikeMTB1.1 mi Darien HS trailHike1.1 mi The Jones TrailHike1.1 mi Eureka Lake PathHike1.0 mi Pinchbeck TrailHike1.0 mi Dayton TrailHike1.0 mi Hemlock TrailHike1.0 mi Wilderness RoadHike1.0 mi Turkington Falls LoopHike1.0 mi Purple TrailHikeMTB0.9 mi Saddleback TrailHike0.9 mi Dan Beard TrailHike0.9 mi Reeve Biggers TrailHike0.9 mi Byram TrailHike0.9 mi Captain's TrailHike0.9 mi Shippan Landing Public Waterfront PathwayHike0.9 mi Perimeter TrailHike0.9 mi Pent TrailHike0.9 mi Knapp TrailHikeMTB0.8 mi BHike0.8 mi Ippoliti TrailHikeMTB0.8 mi Wall TrailHike0.8 mi Donahue TrailHike0.8 mi Norwalk River Valley Trail ReddingHike0.8 mi Red Maple TrailHike0.8 mi Swingset TrailHikeMTB0.8 mi West Mountain Refuge North LoopHike0.8 mi Old Pasture TrailHike0.7 mi Cutoff TrailHike0.7 mi Old Sib Preserve LoopHike0.7 mi Ambler TrailHike0.7 mi Hillside TrailHike0.7 mi Indian Mill TrailHike0.7 mi Second Loop TrailHikeMTB0.7 mi Fairchild RoadHike0.7 mi Harbor Loop TrailHikeMTB0.6 mi River RoadHikeMTB0.6 mi The NooseHike0.6 mi Split Rock TrailHike0.6 mi Sandy's TrailHike0.6 mi Deer Knoll TrailHike0.6 mi GreenHikeMTB0.6 mi Deer Run TrailHike0.6 mi Dogwood LaneHike0.6 mi Tulip Tree LoopHike0.6 mi East Starrs Plain Road White TrailHike0.6 mi Indian Rock TrailHikeMTB0.6 mi Boulder TrailHike0.6 mi river walkHike0.6 mi The Fifth ConnecticutHike0.6 mi Ives SpurHike0.6 mi Norwalk River Environment Study TrailHikeMTB0.5 mi The DrummerHike0.5 mi Harp TrailHike0.5 mi White Furlough TrailHike0.5 mi Dark Hollow TrailHike0.5 mi Halo TrailHike0.5 mi Jennings Woods PathHike0.5 mi Spc Wilfredo Perez Jr. TrailHikeMTB0.5 mi Pond LoopHike0.5 mi Red Blazed TrailHike0.5 mi Riverwalk TrailHikeMTB0.5 mi ADA TrailHike0.5 mi Fisherman's Loop TrailHikeMTB0.5 mi White Oak TrailHike0.5 mi Brook TrailHike0.5 mi Cave TrailHike0.5 mi Swamp TrailHikeMTB0.5 mi Jamice's LoopHike0.5 mi Deer TrailHikeMTB0.5 mi Den TrailHike0.4 mi Long View TrailHike0.4 mi Synchrony StrollHike0.4 mi Hattertown Pond Trail01Hike0.4 mi The LariatHike0.4 mi GreenlinkHike0.4 mi Cub Scout TrailHike0.4 mi Red Oak TrailHike0.4 mi Pine Hill RoadHike0.4 mi Beech Hill TrailHike0.4 mi Freeborn White TrailHike0.4 mi Scalzi RiverwalkHike0.4 mi McDougal Trail WestHike0.4 mi McDougal WestHike0.4 mi Baldy Ridge TrailHike0.4 mi Forest RoadHike0.4 mi Goodwill TrailHike0.4 mi Crossover TrailHike0.4 mi Wheels in the Woods #7HikeMTB0.4 mi Huntington Ridge TrailHike0.4 mi West Mountain Refuge South TrailHike0.4 mi Yovan TrailHike0.4 mi Saul's LoopHike0.4 mi Kay's trailHike0.4 mi Casey Lane TrailHike0.3 mi GHike0.3 mi Hill TrailHike0.3 mi Harrison TrailHike0.3 mi RHike0.3 mi TopledgeHike0.3 mi West Mountain Refuge North Link to RoadHike0.3 mi Enchanted TrailHike0.3 mi Beaver Pond LoopHike0.3 mi Access WayHike0.3 mi Katharine Hill TrailHike0.3 mi McDougal EastHike0.3 mi McDougal Trail EastHike0.3 mi Grey Glen RoadHike0.3 mi Meander TrailHike0.3 mi Silo TrailHike0.3 mi The AlleeHike0.3 mi Ives TrailHike0.3 mi Kelly Slide TrailHike0.3 mi West Mtn South Cliff LoopHike0.3 mi Boulder Top TrailHike0.3 mi Wetland WalkHike0.3 mi Northeast PassageHike0.3 mi Bromson Private TrailHike0.3 mi RiverwalkHike0.3 mi Treehouse TrailHike0.3 mi Wielh TrailHike0.3 mi Field TrailHike0.3 mi Cabin TrailHike0.3 mi Yellow blazed trailHike0.3 mi Azalea TrailHike0.2 mi Universal Access TrailHike0.2 mi Rhododendron LaneHike0.2 mi West River TrailHike0.2 mi Bird Sanctuary TrailHike0.2 mi Old Field TrailHike0.2 mi South TopstoneHike0.2 mi Beech TrailHike0.2 mi Rock Rimmon to Fishing Trail PathHikeMTB0.2 mi Discovery TrailHike0.2 mi The CrossoverHike0.2 mi Greenlink TrailHike0.2 mi Dam TrailHike0.2 mi Old Logging RoadHike0.2 mi Ridge RunHike0.2 mi Old Redding Road TrailHike0.2 mi Todd's Woods TrailHike0.2 mi Horan Park RiverwalkHike0.2 mi West Mtn TrailHike0.2 mi Middle TrailHike0.2 mi Cemetery TrailHike0.2 mi Base TrailHike0.2 mi Baker park trailHike0.2 mi Orange & White TrailHikeMTB0.2 mi Old Trolley PathHike0.2 mi Old Forest TrailHike0.2 mi Ski LoopHike0.2 mi Deer Hill Road ConnectorHike0.2 mi Poplar TrailHikeMTB0.2 mi High-Point TrailHike0.2 mi Swizzle TrailHike0.2 mi Hillside Annex Walking PathHike0.2 mi Meadow RoadHike0.2 mi Big Trees TrailHike0.2 mi Azalea RoadHike0.2 mi The LedgeHike0.2 mi OHike0.2 mi Todd's Wood ConnectorHike0.2 mi Historical Society TrailHike0.2 mi Joe's Creek TrailHike0.2 mi Watercan TrailHike0.2 mi Peak TrailHike0.2 mi Mill River GreenwayHikeMTB0.2 mi Accessible TrailHike0.1 mi Dog Walking PathHikeMTB0.1 mi Kelley Slide TrailHike0.1 mi Eureka Lake AccessHike0.1 mi Blue ConnectorHike0.1 mi Summit TrailHike0.1 mi Jill TrailHike0.1 mi Great Ledge TrailHike0.1 mi Dog Entry PathHike0.1 mi Halley's Comet TrailHike0.1 mi YHike0.1 mi Drop-Off TrailHike0.1 mi Pierrepont Park TrailHike0.1 mi NVRT (part of)Hike0.1 mi Universal Access ConnectorHike0.1 mi Cliff House & Turtle PondHike0.1 mi The Knoll TrailHike0.1 mi NRVT to Buckingham RidgeHike0.1 mi Grove TrailHike0.1 mi Herrick TrailHike0.1 mi

← All Western Connecticut Planning Region 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.