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Litchfield Hills

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326 mi 524 km of trail 3 Runs

Easy Trails 54 Trails Intermediate Trails 68 Trails Hard Trails 21 Trails
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Runs in Litchfield Hills - 3

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Favorite Stunning views from Cobble Mountain
Difficult

Macedonia Ridge Trail

6.4 mi 10.3 km • Point to Point • 1,592 ft Ascent 485.14 m Ascent

(10) Kent, CT
Favorite Bear Mountain Peak
Intermediate

Bear Mountain

5.4 mi 8.7 km • Out and Back • 1,549 ft Ascent 472.12 m Ascent

(3) Salisbury, CT
Favorite A 2.7 mile hike through a thick forest landscape ends with this amazing expanse - Rands View, with Wetauwanchu Mountain on the left, and Bear Mountain and Mount Everett in Massachusetts on the horizon.
Difficult

Rand's View Out and Back

5.4 mi 8.7 km • Out and Back • 1,110 ft Ascent 338.19 m Ascent

(3) Canaan, CT

Trails in Litchfield Hills - 140

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1.2 mi 2.0 km #1Lion's Head Trail
Difficult
Canaan, CT
Difficult
1.2 mi 2.0 km Canaan, CT
1.7 mi 2.7 km #2Pomperaug Trail - Blue
Difficult
Southbury, CT
Difficult
1.7 mi 2.7 km Southbury, CT
3.3 mi 5.3 km #3Jericho Trail
Difficult
Oakville, CT
Difficult
3.3 mi 5.3 km Oakville, CT
0.4 mi 0.7 km #4Quarry Trail
Difficult
West Torrington, CT
Difficult
0.4 mi 0.7 km West Torrington, CT
1.7 mi 2.8 km #5Crest Trail - Blue/White
Difficult
Southbury, CT
Difficult
1.7 mi 2.8 km Southbury, CT
18.1 mi 29.1 km #6Quinnipiac Trail
Difficult
Cheshire Village, CT
Difficult
18.1 mi 29.1 km Cheshire Village, CT
2.7 mi 4.4 km #7Mt. Frissell Trail
Difficult
Canaan, CT
Difficult
2.7 mi 4.4 km Canaan, CT
1.9 mi 3.0 km #8Under Mountain Trail
Intermediate
Canaan, CT
Intermediate
1.9 mi 3.0 km Canaan, CT
51.6 mi 83.1 km #9AT: AMC - Connecticut Chapter (CT/NY)
Intermediate
Sherman, CT
Intermediate
51.6 mi 83.1 km Sherman, CT
1.8 mi 2.8 km #10Miller Trail - Blue
Intermediate
Southbury, CT
Intermediate
1.8 mi 2.8 km Southbury, CT
26.8 mi 43.1 km #11Mattatuck Trail
Intermediate
Litchfield, CT
Intermediate
26.8 mi 43.1 km Litchfield, CT
2.0 mi 3.2 km #12Bee Brook Loop
Intermediate
New Preston, CT
Intermediate
2.0 mi 3.2 km New Preston, CT
1.7 mi 2.8 km #13Pinnacle Trail
Intermediate
New Preston, CT
Intermediate
1.7 mi 2.8 km New Preston, CT
1.8 mi 3.0 km #14Paradise Lane Trail
Intermediate
Salisbury, CT
Intermediate
1.8 mi 3.0 km Salisbury, CT
34.4 mi 55.4 km #15Tunxis Trail
Intermediate
Terryville, CT
Intermediate
34.4 mi 55.4 km Terryville, CT
1.4 mi 2.3 km #16Roaring Brook Trail
Intermediate
Cheshire, CT
Intermediate
1.4 mi 2.3 km Cheshire, CT
0.8 mi 1.3 km #17Mohawk Trail
Intermediate
New Preston, CT
Intermediate
0.8 mi 1.3 km New Preston, CT
3.8 mi 6.1 km #18Steep Rock Loop
Intermediate
New Preston, CT
Intermediate
3.8 mi 6.1 km New Preston, CT
5.2 mi 8.3 km #19Naugatuck Trail
Intermediate
Naugatuck, CT
Intermediate
5.2 mi 8.3 km Naugatuck, CT
3.4 mi 5.4 km #20Mine Hill Main Trail (Blue Trail)
Intermediate
New Milford, CT
Intermediate
3.4 mi 5.4 km New Milford, CT

Photos of Litchfield Hills - 59

Trail Run Project is built by runners like you. Add Your Photos

Roaring Brook Falls
Nov 11, 2015 near Prospect, CT
View looking north from Round Mountain (El 2280ft.)
Aug 27, 2018 near Canaan, CT
Stunning views from Cobble Mountain
Dec 30, 2017 near Kent, CT
Cobble Mountain view
Dec 30, 2017 near Kent, CT
The river.  Jump in!
Jul 17, 2015 near Kent, CT
Thayer Brook makes a great place for water and a rest.
Jun 24, 2017 near Kent, CT
Overlook
Mar 25, 2020 near Seymour, CT
Trail
Mar 25, 2020 near Seymour, CT

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