About hiking in Northwest Hills Planning Region

Northwest Hills Planning Region, Connecticut has 242 named trails tagged for hiking, covering 518 miles, an average of 2.1 miles each. The longest is hiking, at 141 miles. 11 run 5 miles or longer.

What the hiking trails in Northwest Hills Planning Region are like

By length, 137 are under a mile, 94 run 1 to 5 miles, and 11 are 5 miles or longer. 26 are loops, ending where they start; the longest is Macedonia Ridge Trail, at 6.4 miles.

Every one carries a difficulty rating: 93 easy, 142 moderate, and 7 hard. Of the 241 with measured elevation, hiking climbs the most, about 18,823 ft, and 14 gain 1,000 ft or more.

All 242 hiking trails, longest first

hikingHike141 mi Tunxis TrailHike35.6 mi Mohawk TrailHike22.2 mi Mattatuck TrailHike22.2 mi Tunxis Blue-White TrailHike9.3 mi Blue-Yellow TrailHike8.9 mi Norbrook Bike TrailsHike7.9 mi Norbrook Woods RoadsHike7.6 mi Macedonia Ridge TrailHike6.4 mi Yellow TrailHike5.7 mi Iron Mountain TrailHike5.2 mi Red TrailHike4.7 mi Yellow Diamond TrailHike4.7 mi Mount Easter RoadHikeMTB4.6 mi Green TrailHike4.3 mi Steep Rock LoopHike3.9 mi D'Alton Inner Loop TrailHike3.8 mi Henry Buck TrailHike3.3 mi Queen of Diamonds LoopHike3.1 mi Blue-Orange TrailHike3.1 mi Old Meekertown RoadHike3.0 mi Red Mountain TrailHike2.9 mi Stoney Lonesome TrailHike2.9 mi Cerulean Warbler LoopHike2.8 mi Hal Borland Memorial TrailHike2.7 mi Charcoal Pit TrailHike2.6 mi Agnes Bowen TrailHike2.6 mi Echo Rock SpurHike2.5 mi Crissey TrailHike2.5 mi Beaver PondHike2.4 mi Pine Knob Loop TrailHike2.4 mi Phillips Farm White BlazeHike2.4 mi Wolf Hill Loop TrailHike2.3 mi White TrailHike2.3 mi Clamshell LoopHike2.3 mi Robet Ross TrailHike2.2 mi Kress Family TrailHike2.2 mi Nature Center ConnectorHike2.2 mi Pinney LoopHike2.1 mi Blue TrailHike2.1 mi Purple TrailHike2.1 mi Charles Pack TrailHike2.0 mi Von Ahn Preserve - Loop TrailHike2.0 mi Woodcock TrailHike1.9 mi Elliot Bronson Trail (blue/red)Hike1.9 mi Elliott Bronson TrailHike1.9 mi Shelter Four Loop TrailHike1.9 mi Pine Mountain TrailHike1.9 mi Undermountain TrailHike1.8 mi Laurel TrailHike1.8 mi Billings TrailHike1.8 mi White-Yellow TrailHike1.8 mi Orange TrailHike1.7 mi John Ross TrailHike1.7 mi Meeker TrailHike1.6 mi Tower TrailHike1.6 mi Pink TrailHike1.6 mi Haystack Tower Loop TrailHike1.6 mi East Summit TrailHike1.6 mi Paradise Lane TrailHike1.6 mi Punch Brook TrailHike1.5 mi Botelle Nature TrailHike1.5 mi Billings Trail-Tait SectionHikeMTB1.5 mi Billings Trail:Tait SectionHike1.5 mi Little Pond TrailHike1.5 mi Pine Mountain RoadHikeMTB1.5 mi John Brown TrailHike1.5 mi Jessie Gerard TrailHike1.5 mi Caesar Brook TrailHike1.5 mi Goodbody Loop TrailHike1.4 mi Goodbody Preserve Loop TrailHike1.4 mi Sharon Mountain Preserve Loop TrailHike1.4 mi Fosters Pond TrailHike1.3 mi Ridge TrailHike1.3 mi Rail TrailHike1.3 mi Schaghticoke Mountain TrailHike1.3 mi Bronson Fields TrailHike1.3 mi Twin Oaks TrailsHike1.2 mi Benton Hill TrailHike1.2 mi Hay Field LoopHike1.2 mi Tobey Bog TrailHike1.2 mi Sandy Brook TrailHike1.2 mi Graham Thompson TrailHike1.2 mi Old Carriage TrailHikeMTB1.2 mi Tunxis Blue-Red North TrailHike1.2 mi Northern LoopHike1.2 mi Pond TrailHike1.2 mi Interpretive TrailHike1.1 mi Gold RoadHikeMTB1.1 mi Valley Overlook TrailHike1.1 mi Mountain View TrailHike1.1 mi Tunxis Blue-Red South TrailHike1.1 mi Pope Preserve loop trailHike1.1 mi Guerdat RoadHikeMTB1.1 mi Deerhill TrailHike1.1 mi Tracy RoadHikeMTB1.1 mi D'Alton Outer Loop TrailHike1.0 mi Sam Yankee TrailHike1.0 mi Plunge Pool TrailHike1.0 mi Overlook TrailHike1.0 mi Former Tunxis TrailHike1.0 mi Saturday Afternoon TrailHike1.0 mi Twin Oaks Field TrailHike1.0 mi High Pocket Swamp TrailHike1.0 mi Skiff Mtn North Loop TrailHike1.0 mi Butler TrailHike1.0 mi David K. Leff TrailHike1.0 mi Satan'S Kingdom RoadHikeMTB1.0 mi Steve Quinn Memorial Bike TrailHike1.0 mi Crissey Ridge TrailHike0.9 mi Shinar TrailHike0.9 mi Five Points Connector TrailHike0.9 mi Holiday House LoopHike0.9 mi South LoopHike0.9 mi Cobble Mountain TrailHike0.9 mi North Dam TrailHikeMTB0.9 mi Bear Mountain RoadHikeMTB0.9 mi SherpaHike0.9 mi Starks RoadHikeMTB0.9 mi Skilton TrailHike0.8 mi Songbird TrailHike0.8 mi North Kent RoadHike0.8 mi AnvilHike0.8 mi Yellow Tape TrailHike0.8 mi Brinsmade LoopHike0.8 mi TraverseHike0.8 mi Edith M. Chase Ecology TrailHike0.8 mi LongshotHike0.8 mi Waramaug TrailHike0.8 mi Summit TrailHike0.8 mi Mary Moore Cliff TrailHike0.8 mi Ells Crane TrailHike0.7 mi Red Gate TrailHike0.7 mi Hamlin Ledge LoopHike0.7 mi Hubbell RoadHike0.7 mi Northwest RoadHike0.7 mi Slab Meadow North TrailHike0.7 mi Long Pond TrailHike0.7 mi Old Carriage Road TrailHikeMTB0.7 mi Taine Mountain Road Blue TrailHike0.7 mi Yoakum Preserve Access TrailHike0.7 mi Dive BombHike0.7 mi Slab Meadow South LoopHike0.7 mi Devaux RoadHikeMTB0.7 mi Bucksbaum TrailHike0.7 mi CCT Yellow TrailHike0.7 mi Fiske H. Ventres Bird TrailHike0.6 mi CoeHike0.6 mi Hale TrailHike0.6 mi Blue-Green TrailHike0.6 mi Blue Tape Trail NorthHike0.6 mi Fawn PondHike0.6 mi Red Oak TrailHike0.6 mi Camelback RoadHike0.6 mi Double DownHike0.6 mi Horse TrailHike0.6 mi Heron PondHike0.6 mi Mountain TrailHike0.6 mi Barnum LoopHike0.6 mi Blue Tape Trail SouthHike0.6 mi Bowne Road Spur TrailHike0.6 mi Story Walk TrailHike0.6 mi Flying SquirrelHike0.6 mi Donkey PathHike0.5 mi Caleb's Peak TrailHike0.5 mi Bernard Stairs TrailHike0.5 mi Fox Brook TrailHike0.5 mi Lost Camp TrailHike0.5 mi Dirt SessionsHike0.5 mi Sunset TrailHikeMTB0.5 mi Old OakHike0.5 mi South Dam TrailHikeMTB0.5 mi Aranow TrailHike0.5 mi Charcoal TrailHike0.5 mi Moosewood TrailHike0.5 mi Tree Identification TrailHike0.5 mi Heron Pond RidgeHike0.5 mi Benton Hill Route 343 SpurHike0.5 mi Rail-trailHikeMTB0.5 mi Paradise Group Campsite TrailHike0.5 mi Ballyhack Preserve TrailHike0.5 mi Tamarack TrailHike0.5 mi Whie Oaks TrailHike0.5 mi Lower TrailHike0.4 mi North LoopHike0.4 mi Kirby Brook RoadHikeMTB0.4 mi Turkey Vulture LedgesHike0.4 mi Crosscut TrailHike0.4 mi Warm UpHike0.4 mi Dim RedHike0.4 mi Crossover TrailHike0.4 mi Surdan Mountain TrailHike0.4 mi Trinity Forest TrailHike0.4 mi Lower Sages Ravine TrailHike0.4 mi Swamp TrailHike0.4 mi Van Ingen TrailHike0.4 mi Hillside LoopHike0.4 mi Teal PondHike0.4 mi Baldwin RoadHikeMTB0.4 mi Wynne Road AccessHike0.4 mi Big DipperHikeMTB0.4 mi Goodbody/Von Ahn Connecting TrailHike0.4 mi East Street Spur TrailHike0.4 mi Electric Park TrailHike0.4 mi Trolley RouteHike0.4 mi Waterfall TrailHike0.3 mi Escarpment TrailHike0.3 mi Hoop Pole Hill RoadHike0.3 mi Spring Hill RoadHikeMTB0.3 mi Rockwell TrailHike0.3 mi Phillips Farm White/Blue BlazeHike0.3 mi White-Red TrailHike0.3 mi Norfolk Meadow BoardwalkHike0.3 mi Beech Hill Loop TrailHikeMTB0.3 mi Entry TrailHike0.3 mi Northern AccessHike0.2 mi Farnum Fields TrailHike0.2 mi Twin Oaks Farm Road PathHike0.2 mi Too Steep TrailHike0.2 mi Walt Landgraf TrailHike0.2 mi Walt Landgraf Trail (red)Hike0.2 mi D'Alton Parking Spur TrailHike0.2 mi Blue Connector TrailHike0.2 mi CreeksideHike0.2 mi D'Alton Bog Loop TrailHike0.2 mi White-Orange TrailHike0.2 mi Chalybes Road WestHike0.2 mi Skiff Green TrailHike0.2 mi White-Red-Dot TrailHike0.2 mi White-Yellow-Dot TrailHike0.2 mi Falls Cut Off TrailHike0.2 mi Skiff Mtn North Parking Spur TrailHike0.2 mi Short Loop TrailHike0.2 mi Garrett Goodbody Trail SpurHike0.2 mi Brook TrailHikeMTB0.2 mi Jump LineHike0.2 mi Schaghticoke Mountain Campsite TrailHike0.1 mi Hemlock TrailHike0.1 mi Balance Rock TrailHike0.1 mi Black Spruce Bog TrailHike0.1 mi Wolf Tree ConnectorHike0.1 mi Lighthouse TrailHike0.1 mi

← All Northwest Hills 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.