Best Hiking Trails in Connecticut | Trailmonger

About hiking in Connecticut

Connecticut has 1,776 named trails tagged for hiking on the map, covering 3,421 miles, an average of 1.9 miles each. The longest is hiking in Lower Connecticut River Valley Planning Region, at 231 miles. 78 run 5 miles or longer. 9 of the state's counties have at least one; Capitol Planning Region has the most, with 413 trails.

Top 100 hiking trails, longest first

hikingHikeLower Connecticut River Valley Planning Region231 mi hikingHikeSouth Central Connecticut Planning Region181 mi hikingHikeCapitol Planning Region179 mi hikingHikeNorthwest Hills Planning Region141 mi hikingHikeWestern Connecticut Planning Region118 mi hikingHikeNaugatuck Valley Planning Region74.5 mi New England National Scenic TrailHikeCapitol Planning Region57.5 mi Metacomet TrailHikeCapitol Planning Region55.8 mi hikingHikeSoutheastern Connecticut Planning Region49.0 mi hikingHikeGreater Bridgeport Planning Region41.2 mi Shenipsit TrailHikeCapitol Planning Region38.6 mi Tunxis TrailHikeNorthwest Hills Planning Region35.6 mi Yellow TrailHikeCapitol Planning Region32.5 mi hikingHikeNortheastern Connecticut Planning Region25.7 mi Mohawk TrailHikeNorthwest Hills Planning Region22.2 mi Mattatuck TrailHikeNorthwest Hills Planning Region22.2 mi Nipmuck TrailHikeNortheastern Connecticut Planning Region20.6 mi Pachaug TrailHikeNortheastern Connecticut Planning Region20.1 mi Hockanum River Linear ParkHikeCapitol Planning Region19.4 mi Mattabesett TrailHikeSouth Central Connecticut Planning Region17.3 mi New England TrailHikeSouth Central Connecticut Planning Region17.3 mi Natchaug TrailHikeNortheastern Connecticut Planning Region17.3 mi The Branford TrailHikeSouth Central Connecticut Planning Region16.7 mi Norwalk River Valley TrailHikeMTBWestern Connecticut Planning Region16.4 mi Menunkatuck TrailHikeSouth Central Connecticut Planning Region16.1 mi Quinebaug River TrailHikeMTBNortheastern Connecticut Planning Region15.6 mi Quinnipiac TrailHikeSouth Central Connecticut Planning Region14.1 mi Mission 22 TrailHikeNaugatuck Valley Planning Region14.1 mi Blue TrailHikeCapitol Planning Region13.5 mi Ives Trail GreenwayHikeWestern Connecticut Planning Region13.4 mi Red TrailHikeCapitol Planning Region12.8 mi Hop River State Park TrailHikeMTBCapitol Planning Region12.7 mi Zoar TrailHikeWestern Connecticut Planning Region12.7 mi Orange TrailHikeCapitol Planning Region11.6 mi Blue TrailHikeNaugatuck Valley Planning Region11.6 mi White TrailHikeSouth Central Connecticut Planning Region11.3 mi White TrailHikeLower Connecticut River Valley Planning Region10.8 mi Deep Woods TrailHikeLower Connecticut River Valley Planning Region10.3 mi Al's TrailHikeWestern Connecticut Planning Region10.0 mi Red TrailHikeNaugatuck Valley Planning Region9.6 mi Saugatuck TrailHikeWestern Connecticut Planning Region9.5 mi Richard H. Goodwin TrailHikeSoutheastern Connecticut Planning Region9.4 mi Moore TrailHikeLower Connecticut River Valley Planning Region9.3 mi Paugussett TrailHikeNaugatuck Valley Planning Region9.3 mi Tunxis Blue-White TrailHikeNorthwest Hills Planning Region9.3 mi Blue-Yellow TrailHikeNorthwest Hills Planning Region8.9 mi Air Line State Park TrailHikeMTBSoutheastern Connecticut Planning Region8.9 mi Pequot TrailHikeSoutheastern Connecticut Planning Region8.6 mi Shelton Lakes Recreation PathHikeNaugatuck Valley Planning Region8.3 mi Air Line State Park TrailHikeMTBNortheastern Connecticut Planning Region8.0 mi Norbrook Bike TrailsHikeNorthwest Hills Planning Region7.9 mi Naugatuck Trail (Woodbridge)HikeSouth Central Connecticut Planning Region7.9 mi Norbrook Woods RoadsHikeNorthwest Hills Planning Region7.6 mi Lone Pine TrailHikeSouth Central Connecticut Planning Region7.6 mi Narragansett trail (CT)HikeSoutheastern Connecticut Planning Region7.4 mi Nehantic TrailHikeNortheastern Connecticut Planning Region7.4 mi White TrailHikeCapitol Planning Region7.2 mi Cockaponset TrailHikeLower Connecticut River Valley Planning Region7.0 mi Regicides TrailHikeSouth Central Connecticut Planning Region6.9 mi East Woods TrailHikeLower Connecticut River Valley Planning Region6.8 mi Deer Pond Farm TrailsHikeWestern Connecticut Planning Region6.7 mi Nipmuck Trail - East BranchHikeCapitol Planning Region6.5 mi Quinebaug TrailHikeNortheastern Connecticut Planning Region6.5 mi Godfrey TrailHikeWestern Connecticut Planning Region6.4 mi Macedonia Ridge TrailHikeNorthwest Hills Planning Region6.4 mi Yellow TrailHikeLower Connecticut River Valley Planning Region6.3 mi Horse TrailHikeSouth Central Connecticut Planning Region6.2 mi Yellow TrailHikeSoutheastern Connecticut Planning Region6.1 mi Carriage PathHikeCapitol Planning Region6.0 mi Housatonic Range TrailHikeWestern Connecticut Planning Region5.8 mi Aspetuck Valley TrailHikeWestern Connecticut Planning Region5.7 mi Chatfield TrailHikeLower Connecticut River Valley Planning Region5.7 mi Lillinoah TrailHikeWestern Connecticut Planning Region5.6 mi White TrailHikeNaugatuck Valley Planning Region5.3 mi Nipmuck Trail - West BranchHikeCapitol Planning Region5.2 mi Iron Mountain TrailHikeNorthwest Hills Planning Region5.2 mi Northern ExposureHikeLower Connecticut River Valley Planning Region5.1 mi Hop River Linear ParkHikeMTBCapitol Planning Region5.0 mi Green TrailHikeCapitol Planning Region4.9 mi Hardwood TrailHikeWestern Connecticut Planning Region4.8 mi Pachaug Enduro TrailHikeMTBNortheastern Connecticut Planning Region4.7 mi Outer Loop TrailHikeCapitol Planning Region4.7 mi Yellow Diamond TrailHikeNorthwest Hills Planning Region4.7 mi Metacomet Loop TrailHikeCapitol Planning Region4.7 mi Red TrailHikeMTBWestern Connecticut Planning Region4.7 mi Blue TrailHikeSouth Central Connecticut Planning Region4.7 mi BlueHikeMTBWestern Connecticut Planning Region4.7 mi Natchaug Forest TrailHikeMTBNortheastern Connecticut Planning Region4.6 mi Salmon River TrailHikeSoutheastern Connecticut Planning Region4.6 mi Mount Easter RoadHikeMTBNorthwest Hills Planning Region4.6 mi Mashapaug Pond View TrailHikeNortheastern Connecticut Planning Region4.6 mi Yellow TrailHikeNaugatuck Valley Planning Region4.5 mi Ridge TrailHikeMTBSouth Central Connecticut Planning Region4.5 mi Pomperaug TrailHikeNaugatuck Valley Planning Region4.4 mi Yellow LoopHikeWestern Connecticut Planning Region4.4 mi Laurel Loop TrailHikeNortheastern Connecticut Planning Region4.4 mi Shoreline TrailHikeNortheastern Connecticut Planning Region4.3 mi Pomparaug TrailHikeNaugatuck Valley Planning Region4.3 mi Filley RoadHikeMTBLower Connecticut River Valley Planning Region4.3 mi Red TrailHikeSouth Central Connecticut Planning Region4.3 mi

Hiking Trails by county

Capitol Planning Region

Western Connecticut Planning Region

South Central Connecticut Planning Region

Northwest Hills Planning Region

Lower Connecticut River Valley Planning Region

Southeastern Connecticut Planning Region

Naugatuck Valley Planning Region

Northeastern Connecticut Planning Region

Greater Bridgeport Planning Region

← All of Connecticut

Trail geometry from OpenStreetMap contributors, licensed ODbL. Elevation from the USGS 3D Elevation Program. Compiled and published by Trailmonger · trail data last rebuilt August 28, 2026.