Bridgeport · CT

Hiking trails near Bridgeport, CT

568 trails within 75 miles · 17 with detail pages · 260 within 25 miles

This page lists every named hiking trail in our database whose centroid sits within 75 miles of Bridgeport. Distance is straight-line from the metro center to the trail's centroid; an actual drive to a trailhead may be longer or shorter depending on which end you start from. Multi-state trails (e.g. the Appalachian Trail) appear here if any portion of their length passes within range.

Always check trail conditions, permits, and water sources with the maintaining organisation — National Park Service, U.S. Forest Service ranger district, or trail association. Mountain trails are often impassable for half the year due to snow.

Closest trails to Bridgeport

Top 5

Connecticut · 13 mi

Paugussett Trail

10 miles from Bridgeport · ~20 min

Connecticut

Saugatuck Trail

11 miles from Bridgeport · ~20 min

Connecticut

Aspetuck Valley Trail

11 miles from Bridgeport · ~20 min

Connecticut

Ives Trail Greenway Alternative

18 miles from Bridgeport · ~30 min

Connecticut

Ives Trail Greenway

18 miles from Bridgeport · ~30 min

All trails within 75 miles, by distance

568 total

Within 25 miles of Bridgeport

260 listed
TrailLengthNetworkFrom metroDrive
Yellow Trail—Local4 mi~5 min
White Trail—Local5 mi~10 min
Putnam Preserve Trail—Local6 mi~10 min
Gristmill Trail—Local7 mi~10 min
Randall's Farm Preserve Trail—Local7 mi~15 min
Wesley Waterfall Loop—Local8 mi~15 min
Pink Trail (Off Leash Loop)—Local8 mi~15 min
Basil Brook Bypass1 miLocal8 mi~15 min
Freeborn White Trail—Local8 mi~15 min
Nell's Rock Trail—Local9 mi~15 min
Paul Busch Trail—Local9 mi~15 min
Eklund Bypass—Local9 mi~15 min
Flower Path—Local9 mi~15 min
Oak Valley Trail—Local9 mi~15 min
Ruth’s Trail—Local9 mi~15 min
Ordway Trail—Local9 mi~15 min
Princie's Way—Local9 mi~15 min
Turkey Trot Trail—Local9 mi~15 min
Silent Waters Canoe Launch—10 mi~15 min
Maple Road Trail—Local10 mi~15 min
Paine Barn Trail—Local10 mi~15 min
Maple Road Trail—Local10 mi~20 min
Pond Trail—Local10 mi~20 min
Oak Hill Trail—Local10 mi~20 min
Nash Trail—Local10 mi~20 min
Evergreen Trail—Local10 mi~20 min
Meadown View—Local10 mi~20 min
Woodland Trail—Local10 mi~20 min
Seven Ponds Trail—Local10 mi~20 min
Bayberry Crossing—Local10 mi~20 min
Apple Tree Crossing Trail—Local10 mi~20 min
Aspetuck Blue Trail—Local10 mi~20 min
Aspetuck Red Trail—Local10 mi~20 min
Laurel Ledges Trail—Local10 mi~20 min
Paugussett Trail13 miRegional10 mi~20 min
Cattail Trail—Local11 mi~20 min
Troop 7 Trail—11 mi~20 min
Saugatuck Trail—Regional11 mi~20 min
Wetland Trail—Local11 mi~20 min
Perry Trail—Local11 mi~20 min
The Allee—Local11 mi~20 min
The Driftway—Local11 mi~20 min
Dog Entry Path—11 mi~20 min
Pillars Trail—Local11 mi~20 min
Deer Knoll Trail—Local11 mi~20 min
Aspetuck Trail—Local11 mi~20 min
ADA Trail—Local11 mi~20 min
McDougal Trail East—Local11 mi~20 min
French's Hill Trail—Local11 mi~20 min
McDougal Trail West—Local11 mi~20 min
Godfrey Trail—Local11 mi~20 min
Hiltebeitel Trail—Local11 mi~20 min
Dayton Trail—Local11 mi~20 min
Sap Brook Trail—Local11 mi~20 min
Aspetuck Valley Trail—Regional11 mi~20 min
Pinchbeck Trail—Local12 mi~20 min
Deer Run Trail—Local12 mi~20 min
Bedford Trail—Local12 mi~20 min
Cedar Cliff Trail—Local12 mi~20 min
Bruzelius Trail—Local12 mi~20 min
Deer Hill Road Connector—Local12 mi~20 min
Ensor's Terrace—Local12 mi~20 min
Universal Access Trail—Local12 mi~20 min
Universal Access Connector—Local12 mi~20 min
Blue Connector—Local12 mi~20 min
Delia Trail—Local12 mi~20 min
Red Trail—Local12 mi~20 min
Blue Connector—Local13 mi~20 min
Two Ridges Trail—Local13 mi~20 min
Blue Access—Local13 mi~20 min
Blue-Yellow Connector—Local13 mi~25 min
John Read Parking Lot Link to Dan Beard Trail—Local13 mi~25 min
Old Field—Local13 mi~25 min
Dan Beard Trail—Local14 mi~25 min
Accessible Trail—Local14 mi~25 min
Dan Beard/Turkington Falls Crossover—Local14 mi~25 min
Hemlock Trail—Local14 mi~25 min
Turkington Falls Loop—Local14 mi~25 min
Cutoff Trail—Local14 mi~25 min
Burn Trail—Local14 mi~25 min
Falls Trail—Local14 mi~25 min
Reeve Biggers/Turkington Falls Cutover—Local14 mi~25 min
Knapp Way—Local14 mi~25 min
The Cricket Trail—Local14 mi~25 min
Oak Trail—Local14 mi~25 min
Power Line Trail—Local14 mi~25 min
Yovan Trail—Local14 mi~25 min
Reeve Biggers Trail—Local14 mi~25 min
Wall Trail—Local14 mi~25 min
Hardwood Trail—Local14 mi~25 min
The Drummer—Local14 mi~25 min
The Fifth Connecticut—Local14 mi~25 min
Access Way—Local14 mi~25 min
The Noose—Local14 mi~25 min
The Ledge—Local14 mi~25 min
Firehouse Trail—Local15 mi~25 min
Pond Trail—Local15 mi~25 min
Boulder Trail—Local15 mi~25 min
Big Trees Trail—Local15 mi~25 min
Pond Trail—Local15 mi~25 min
The Crossover—Local15 mi~25 min
Orange Trail—15 mi~25 min
The Lariat—Local15 mi~25 min
Split Rock Trail—Local15 mi~25 min
Gneiss Trail—Local15 mi~25 min
The Knoll Trail—Local15 mi~25 min
Todd's Wood Connector—Local15 mi~25 min
Todd's Woods Trail—Local15 mi~25 min
Red Trail1 miLocal15 mi~25 min
Blue Trail0 miLocal15 mi~25 min
Yellow Trail0 miLocal15 mi~25 min
Summit Trail—Local15 mi~25 min
Green Trail0 miLocal15 mi~25 min
Purple Trail1 miLocal15 mi~25 min
Red Maple Trail—Local15 mi~25 min
Dogwood Trail—Local15 mi~25 min
Baldy Ridge Trail—Local15 mi~25 min
Jill Trail—Local15 mi~25 min
White Oak Trail—Local15 mi~25 min
Old Logging Road—Local15 mi~25 min
Perimeter Trail—Local15 mi~25 min
Beech Trail—Local16 mi~25 min
Zoar Trail—Local16 mi~25 min
The Jones Trail—Local16 mi~25 min
Stephenson Trail—Local16 mi~25 min
Pond Loop—Local16 mi~25 min
Jamice's Loop—Local16 mi~30 min
Saul's Loop—Local16 mi~30 min
White Furlough Trail—Local16 mi~30 min
Blue Forlough Trail—Local16 mi~30 min
McCormack White Trail—Local16 mi~30 min
McCormack Blue Trail—Local17 mi~30 min
Miller Trail—Local17 mi~30 min
East Starrs Plain Road White Trail—Local17 mi~30 min
Eureka Lake Path—Local17 mi~30 min
Eureka Lake Connector—Local18 mi~30 min
Old Church Lane Preserve Trail—Local18 mi~30 min
Ives Spur—Local18 mi~30 min
Green Trail—Local18 mi~30 min
Ives Trail Greenway Alternative—Regional18 mi~30 min
Al's Trail—Local18 mi~30 min
White Entrance Trail—18 mi~30 min
Casey Lane Trail—Local18 mi~30 min
Blue Trail—18 mi~30 min
Yellow Trail—18 mi~30 min
Cottage Trail | Pink Trail—18 mi~30 min
Silver Trail—18 mi~30 min
Cross Preserve Trail—18 mi~30 min
South Gorge Rim Trail—18 mi~30 min
Ives Trail Greenway—Regional18 mi~30 min
Green Trail—18 mi~30 min
Orange Trail—18 mi~30 min
White/Ridgefield Ave. Trail—18 mi~30 min
Stream Trail—18 mi~30 min
Tan Trail—18 mi~30 min
White Connector Trail—18 mi~30 min
West Mtn South Cliff Loop—Local19 mi~30 min
West Mtn Trail—Local19 mi~30 min
Hemlock Trail—Local19 mi~30 min
Purple Trail—19 mi~30 min
West Mountain Refuge South Trail—Local19 mi~30 min
Wetland Walk—Local19 mi~30 min
Black Birch Trail—Local19 mi~30 min
Tulip Tree Loop—Local19 mi~30 min
West Mountain Refuge North Loop—Local19 mi~35 min
Red Maple Trail—Local19 mi~35 min
Brook Trail—Local19 mi~35 min
Pond Trail—Local19 mi~35 min
Red Oak Trail—Local19 mi~35 min
West Mountain Refuge North Link to Road—Local19 mi~35 min
Cemetery Trail—Local19 mi~35 min
White Trail—Local19 mi~35 min
Red Trail—Local19 mi~35 min
White Trail—Local19 mi~35 min
Green Trail—Local20 mi~35 min
Lillinoah Trail—Local20 mi~35 min
White-Blue-Dot Trail—Local20 mi~35 min
White-Purple-Dot—Local20 mi~35 min
Al's trail—Regional20 mi~35 min
Yellow Trail—Local20 mi~35 min
White-Red-Dot—Local20 mi~35 min
Blue Trail—Local20 mi~35 min
Blue Trail—Local20 mi~35 min
White Trail—Local20 mi~35 min
Yellow Trail—Local20 mi~35 min
Blue Trail—Local20 mi~35 min
White Trail—Local20 mi~35 min
Red Trail—Local20 mi~35 min
Blue Trail—Local20 mi~35 min
Old Sib Preserve Loop—Local20 mi~35 min
Green Trail0 miLocal20 mi~35 min
Blue Trail2 miLocal21 mi~35 min
Yellow Trail—21 mi~35 min
Yellow Trail2 miLocal21 mi~35 min
Blue Connector—Local21 mi~35 min
White Trail1 miLocal21 mi~35 min
Hemlock Lake Trail—Local21 mi~35 min
Deer Hollow Trail4 miLocal21 mi~35 min
Red Trail—Local21 mi~35 min
Old Sib Trail2 miLocal21 mi~35 min
Red Trail0 miLocal21 mi~35 min
Orange Trail4 miLocal21 mi~35 min
Green Trail—21 mi~35 min
White Trail—Local21 mi~35 min
Spruce Lake Trail0 miLocal21 mi~35 min
Brown Trail4 miLocal21 mi~35 min
Fox Hill Trail—21 mi~35 min
Covered Bridge—Local21 mi~35 min
Cabin Trail—21 mi~35 min
Leatherman's Loop2 miLocal21 mi~35 min
Yellow Trail0 mi21 mi~35 min
Yellow Trail—21 mi~35 min
Orange Trail—21 mi~35 min
Blue / Red Trail—21 mi~35 min
Green Trail—22 mi~35 min
White Trail—22 mi~35 min
Blue Trail—22 mi~35 min
Yellow Loop—Local22 mi~35 min
Indian Mill Trail—22 mi~35 min
Laurel Trail—22 mi~40 min
Inner Road—22 mi~35 min
Green Loop—Local22 mi~35 min
Crossover Trail—Local22 mi~35 min
North Salem Trail—22 mi~35 min
Blue Trail1 mi22 mi~35 min
Orange Trail—22 mi~35 min
Beach Access Trail—22 mi~40 min
Main Road—22 mi~40 min
Rocky Beach Trail0 mi22 mi~40 min
Warblers' Loop Trail0 mi22 mi~40 min
Gardener's Path Trail0 mi22 mi~40 min
Yellow Trail—Local22 mi~40 min
Old Farmland Trail—22 mi~40 min
Chipmunk Loop Trail—22 mi~40 min
Todd Pond Trail—22 mi~40 min
Upper River Trail—22 mi~40 min
Lower River Trail—22 mi~40 min
White Trail—22 mi~40 min
Plank Road Trail—22 mi~40 min
Red Trail1 mi23 mi~40 min
Orange Trail—Local23 mi~40 min
Yellow Trail1 mi23 mi~40 min
Green Trail1 mi23 mi~40 min
Blue Trail1 mi23 mi~40 min
Fire Road1 mi23 mi~40 min
Half Mile Nature Trail0 mi23 mi~40 min
Greenbelt Trail2 mi23 mi~40 min
Orange Trail1 mi23 mi~40 min
White Trail—Local24 mi~40 min
Red Trail1 miLocal24 mi~40 min
Yellow Trail—Local24 mi~40 min
White Trail—24 mi~40 min
Blydenburgh Blue Trail—24 mi~40 min
White Trail—24 mi~45 min
Maybrook Trailway (Putnam Trailway - CT Border)—Local25 mi~45 min
Yellow Trail—25 mi~45 min
Red Trail2 mi25 mi~45 min
Brookside Trail0 miLocal25 mi~45 min
Blue Trail—25 mi~45 min
White Trail—25 mi~45 min

25-50 miles

281 listed
TrailLengthNetworkFrom metroDrive
Blue Trail1 mi25 mi~45 min
Spruce Hill Trail0 miLocal25 mi~45 min
Brookhaven Trail3 miLocal25 mi~45 min
Green Trail3 mi25 mi~45 min
Red Trail0 mi25 mi~45 min
Bauer Meadow Hill Trail—25 mi~45 min
Blue Trail0 mi26 mi~45 min
Green Trail0 mi26 mi~45 min
Orange Trail0 mi26 mi~45 min
White Trail0 mi26 mi~45 min
Yellow Trail0 mi26 mi~45 min
Meadow Trail—26 mi~45 min
Black Trail0 mi26 mi~45 min
Hawk Watch Trail0 miLocal26 mi~45 min
Yellow Trail—Local26 mi~45 min
White Trail—26 mi~45 min
Augusta Reese Donohue Trail—26 mi~45 min
The Fern Trail1 miLocal26 mi~45 min
Tarkill Trail—26 mi~45 min
Pine Trail0 mi26 mi~45 min
Butler Trail3 miLocal26 mi~45 min
Connector Trail—Local26 mi~45 min
Balancing Rock Trail0 miLocal26 mi~45 min
Old Goldens Bridge Loop—26 mi~45 min
Orange Trail—26 mi~45 min
Long Island Greenbelt Trail—Regional26 mi~45 min
Diverting Reservoir Trail—Local26 mi~45 min
Daniel P. Davison Trail1 mi26 mi~45 min
Blue Trail—26 mi~45 min
West Loop Trail1 mi26 mi~45 min
Accessible Trail—26 mi~45 min
White Trail—Local26 mi~45 min
Hudson Valley Greenway Trail (Brewster Village)1 miLocal27 mi~45 min
Green Trail—Local27 mi~45 min
Lower Trail—27 mi~45 min
Middle Trail—27 mi~45 min
Cemetery Trail—27 mi~45 min
Upper Trail—27 mi~45 min
Sky Trail—27 mi~50 min
Hillside Trail—27 mi~50 min
Bluebird Trail—27 mi~45 min
High Line—28 mi~50 min
River Walk—28 mi~50 min
Cliffside Trail—28 mi~50 min
Valley Trail—28 mi~50 min
Loop 10 Yellow—28 mi~50 min
Green Loop—Local28 mi~50 min
Kennedy Rail Trail—Local28 mi~50 min
Red Trail—28 mi~50 min
Blue Trail—28 mi~50 min
White Trail—28 mi~50 min
Loop 10a Red—28 mi~50 min
Orange Connector—Local28 mi~50 min
Green Trail—28 mi~50 min
Loop 9 Blue—28 mi~50 min
Yellow Trail—28 mi~50 min
Old Sierra Club Loop—28 mi~50 min
Loop 11—28 mi~50 min
Red Trail—Local28 mi~50 min
Yellow Loop—Local28 mi~50 min
Power Line G Road—28 mi~50 min
Blue Trail—Local28 mi~50 min
Loop 13 Blue—28 mi~50 min
Loop 12—28 mi~50 min
Trail 12 Red—28 mi~50 min
White Trail—Local28 mi~50 min
White Trail—Local28 mi~50 min
Loop 12 Ext—28 mi~50 min
Old Roadway—28 mi~50 min
Yellow Trail—Local28 mi~50 min
Green Trail—Local28 mi~50 min
Blue Trail—28 mi~50 min
Kissenge Trail—28 mi~50 min
Main Loop—29 mi~50 min
Blue and White Access—29 mi~50 min
Blue and White—Local29 mi~50 min
Loop 7 Yellow—29 mi~50 min
Pink and White Connector—Local29 mi~50 min
Blue Trail—29 mi~50 min
Sand Trail—29 mi~50 min
Alex's Trail—29 mi~50 min
Green Fence Trail—29 mi~50 min
Greenway Loop—29 mi~50 min
Walt Whitman Trail—29 mi~50 min
Red Dot Trail—29 mi~50 min
Main Trail—29 mi~50 min
Hickory Trail—Local29 mi~50 min
Hudson Valley Greenway Trail (Mahopac to Brewster)9 miLocal29 mi~50 min
Putnam County Trailway - hiking—Local29 mi~50 min
Loop 6 Red—29 mi~50 min
Hiking Loop—29 mi~50 min
Red and White Trail—29 mi~50 min
Red Loop—Local29 mi~50 min
High Trail—29 mi~50 min
Swamp Loop—Local29 mi~50 min
White Oak Trail—Local29 mi~50 min
Loop 2 Yellow—29 mi~50 min
Loop 8 Red—29 mi~50 min
Avoid Mud 2—29 mi~50 min
Loop 1 Yellow—29 mi~50 min
Loop 3 Blue—29 mi~50 min
Loop 5 Yellow—29 mi~50 min
Loop 4 Yellow—29 mi~50 min
Cliff Trail—Local29 mi~50 min
Hudson Valley Greenway Trail (Brewster to Pawling)9 miLocal30 mi~50 min
Swamp Loop—Local30 mi~50 min
Ridge Walk—Local30 mi~50 min
Boardwalk—30 mi~50 min
Rock Pass Trail—30 mi~50 min
Vernal Pond Trail—30 mi~50 min
Vernal Pond Trail—30 mi~50 min
Deer Pond Farm Trails—Local30 mi~50 min
Ridge Trail—30 mi~50 min
Swamp View Trail—30 mi~50 min
Hilltop Loop—30 mi~50 min
Crystal Springs Trail—30 mi~55 min
Hudson Valley Greenway Trail (New Castle to Mahopac)16 miLocal30 mi~55 min
Kelly Slide Trail—Local30 mi~55 min
Kelley Slide Trail—Local30 mi~55 min
Red Trail—30 mi~55 min
Ledge Trail—Local31 mi~55 min
Old Barn Trail—Local31 mi~55 min
Silo Trail—Local31 mi~55 min
North County Trailway - hiking22 miLocal31 mi~55 min
Nature Trail—Local31 mi~55 min
Hemlock Ravine Trail—31 mi~55 min
Purple Trail—Local31 mi~55 min
Yellow Trail—Local31 mi~55 min
Chestnut Hill Trail—31 mi~55 min
South Spillway Trail0 miLocal31 mi~55 min
Blue Trail—Local31 mi~55 min
Red Trail—Local31 mi~55 min
Housatonic Range Trail—Local31 mi~55 min
Roosevelt Family Walking Trail—32 mi~55 min
Yellow Trail—Local32 mi~55 min
White Trail0 mi32 mi~55 min
Black Trail0 mi32 mi~55 min
North Spillway Trail0 miLocal32 mi~55 min
Yellow Trail—32 mi~55 min
Blue Trail—32 mi~55 min
Teatown-Kitchawan Trail—32 mi~55 min
Highlands Trail—32 mi~55 min
blue—Local32 mi~55 min
Bare Hill0 miLocal32 mi~55 min
Hidden Valley Loop—33 mi~55 min
Overlook Loop—33 mi~55 min
White Trail—33 mi~55 min
Green Trail—Local33 mi~55 min
Phenology Trail—33 mi~55 min
Three Lakes Loop—33 mi~55 min
Vernay Lakeside Connector—33 mi~55 min
Lakeside Loop—33 mi~55 min
Lakeside Overlook Trail—33 mi~55 min
Woodland Loop—Local33 mi~60 min
Shrubland Loop—Local33 mi~60 min
Housatonic Range Trail—Local33 mi~60 min
Cliffdale-Teatown Trail—Local34 mi~60 min
Fitness Trail—34 mi~60 min
Gull Trail—34 mi~60 min
Plover Trail—34 mi~60 min
DuckTrail—34 mi~60 min
Puma Trail—34 mi~60 min
Canine Loop—34 mi~60 min
Raccoon Trail—34 mi~60 min
Beaver Trail—34 mi~60 min
Taconic Bridge Trail—34 mi~60 min
Short Cut—Local34 mi~60 min
Beach Trail—34 mi~60 min
Wren Trail—34 mi~60 min
Fox Trail—34 mi~60 min
Cliffdale Loop—Local34 mi~60 min
Catamount Hill Loop—Local34 mi~60 min
Blue Trail Addition—34 mi~60 min
Yellow Trail—34 mi~60 min
White Trail—34 mi~60 min
Blue Trail—Local34 mi~60 min
Green Trail—34 mi~60 min
Beaver Pond Loop—Local34 mi~60 min
Maybrook Trailway - hiking - Putnam Trailway to Hopewell Junction24 miLocal34 mi~60 min
Red Trail—34 mi~60 min
Pink Trail—35 mi~1.0 hr
Blue Trail—35 mi~1.0 hr
Yellow Trail—35 mi~1.0 hr
Red Trail—Local35 mi~1.0 hr
Terrell River Trail3 miLocal35 mi~1.0 hr
Yellow Trail—Local35 mi~1.0 hr
Croton Gorge Trail—35 mi~1.0 hr
White Trail—Local35 mi~1.0 hr
Lakeview Loop1 miLocal35 mi~1.0 hr
Rock Hill Trail0 miLocal35 mi~1.0 hr
Corner Trail—Local35 mi~1.0 hr
Corner Trail—Local35 mi~1.0 hr
Green Trail—Local36 mi~1.0 hr
Briarcliff-Peekskill Trailway—36 mi~1.0 hr
Purple Trail—36 mi~1.0 hr
Orange Trail—Local36 mi~1.0 hr
Roaring Brook Trail—Local36 mi~1.0 hr
Herrick Trail—Local37 mi~1.1 hr
Myx Monster—37 mi~1.1 hr
Oscawana Ridge Trail—Local37 mi~1.1 hr
My Favorite Trail—38 mi~1.1 hr
Ned's Left Lung—38 mi~1.1 hr
Candlewood Hill Trail—Local38 mi~1.1 hr
Stinger—38 mi~1.1 hr
Limbo—38 mi~1.1 hr
Rambler—38 mi~1.1 hr
Blue Mountain Summit Trail—38 mi~1.1 hr
Rocky Glen—38 mi~1.1 hr
Bailey's—38 mi~1.1 hr
Hudson Valley Greenway Trail (Pawling to Hopewell Junction)15 miLocal38 mi~1.1 hr
Boundary Trail—38 mi~1.1 hr
Lost Bridge—38 mi~1.1 hr
Dickey Brook Trail—38 mi~1.1 hr
Switchback—38 mi~1.1 hr
Hip Hop—38 mi~1.1 hr
Old Mine Railroad Trail—Local38 mi~1.1 hr
Chimney Top Trail—Local39 mi~1.1 hr
Charcoal Burners Trail—Local39 mi~1.1 hr
Catfish Loop—Local39 mi~1.1 hr
Moneyhole Mountain Trail—Local39 mi~1.1 hr
Clove Creek Trail—Local40 mi~1.1 hr
Trout Brook Trail—Local40 mi~1.2 hr
Fahnestock Trail—Local40 mi~1.1 hr
Wiccopee Trail—Local40 mi~1.2 hr
Perkins Trail—Local40 mi~1.2 hr
Perkins Access Trail (Red)—Local40 mi~1.2 hr
Carriage Connector—40 mi~1.2 hr
Osborne Loop—40 mi~1.2 hr
North Redoubt Trail—40 mi~1.2 hr
Round Hill Bypass Trail—Local41 mi~1.2 hr
East Mountain Loop—41 mi~1.2 hr
Camp Smith Trail—Local41 mi~1.2 hr
Sugarloaf Trail—41 mi~1.2 hr
School Mountain Trail—41 mi~1.2 hr
Hubbard Loop—Local41 mi~1.2 hr
Castle Rock Trail—41 mi~1.2 hr
Glenclyffe Loop—41 mi~1.2 hr
Arden Point Trail—41 mi~1.2 hr
Blue Trail—42 mi~1.2 hr
Lonestar Trail—42 mi~1.2 hr
Split Rock Trail—42 mi~1.2 hr
Highlands Trail—42 mi~1.2 hr
Nelsonville Trail—43 mi~1.2 hr
Washburn Trail—43 mi~1.2 hr
Undercliff Trail—43 mi~1.2 hr
Red Trail (Little Stony Point)—43 mi~1.3 hr
Wilkinson Memorial Trail—44 mi~1.3 hr
Blue Trail—44 mi~1.3 hr
Cornish Trail—44 mi~1.3 hr
Fishkill Ridge Trail—44 mi~1.3 hr
Undercliff Bypass Trail (Green)—44 mi~1.3 hr
Cornish Connector Trail—44 mi~1.3 hr
White Trail—44 mi~1.3 hr
Brook Trail—44 mi~1.3 hr
Breakneck Ridge Trail (White)—44 mi~1.3 hr
Overlook Trail—44 mi~1.3 hr
Breakneck Ridge Trail—lcn44 mi~1.3 hr
Casino Trail—Local44 mi~1.3 hr
Nimham Trail—44 mi~1.3 hr
Howell Trail—44 mi~1.3 hr
Stillman Spring Trail—44 mi~1.3 hr
Bobcat Trail—44 mi~1.3 hr
Dry Brook Trail—44 mi~1.3 hr
Notch Trail (blue)—45 mi~1.3 hr
Bypass Trail—45 mi~1.3 hr
Butter Hill Trail—45 mi~1.3 hr
Tower Vue Trail—45 mi~1.3 hr
Honey Hill Trail—45 mi~1.3 hr
Bluebird Trail—45 mi~1.3 hr
Resevoir Trail—45 mi~1.3 hr
Duggan Trail—45 mi~1.3 hr
White Oak Trail—46 mi~1.3 hr
Stillman Trail—46 mi~1.3 hr
Chatfield Trail—46 mi~1.3 hr
Black Rock Hollow Trail—46 mi~1.3 hr
Scenic Trail—46 mi~1.3 hr
Arthur Trail—46 mi~1.3 hr
Compartment Trail—46 mi~1.3 hr
Sackett Trail—Local46 mi~1.3 hr
Dutchess County Rail Trail - hiking - EST13 miLocal47 mi~1.4 hr
Hudson Valley Greenway Trail (Hopewell Junction to Poughkeepsie)13 miLocal47 mi~1.4 hr

50-75 miles

27 listed
TrailLengthNetworkFrom metroDrive
Walkway over the Hudson - hiking—Local53 mi~1.5 hr
Hudson Valley Greenway Trail (Poughkeepsie to New Paltz)13 miLocal56 mi~1.6 hr
Overlook Trail—Local58 mi~1.7 hr
Ridge Trail—Local58 mi~1.7 hr
Ladder Trail—Local58 mi~1.7 hr
North Pond Trail—Local58 mi~1.7 hr
Peninsula Trail—Local58 mi~1.7 hr
Anasa Martin Trail—Local58 mi~1.7 hr
South Pond Trail—Local58 mi~1.7 hr
Chodikee Trail—Local58 mi~1.7 hr
Pond Land Trail—Local59 mi~1.7 hr
Wallkill Valley Rail Trail - hiking22 miLocal62 mi~1.8 hr
Staircliff Path—64 mi~1.8 hr
Skytop Road—64 mi~1.8 hr
The Labyrinth—64 mi~1.8 hr
Lake Shore Road—64 mi~1.8 hr
King's Lane—Regional65 mi~1.9 hr
Upper Awosting Carriageway—66 mi~1.9 hr
Lower Awosting Carriageway—67 mi~1.9 hr
Jenny Lane—67 mi~1.9 hr
Lake Awosting Carriageway—67 mi~1.9 hr
Verkeerderkill Falls Trail—68 mi~2.0 hr
Trail to Stony Kill Falls—68 mi~2.0 hr
Ice Cave Access—69 mi~2.0 hr
High Point Trail—Local69 mi~2.0 hr
High Point Carriageway—69 mi~2.0 hr
Smiley Carriageway—lcn70 mi~2.0 hr

Beyond 75 miles

Wider radius

Looking for trails further out? Browse the full Connecticut hiking list or jump to all U.S. hiking trails.