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Litchfield Hills

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331 mi 532 km of trail 3 Recommended Routes

Easy Trails 58 Trails Intermediate Trails 71 Trails Hard Trails 19 Trails
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Recommended Routes in Litchfield Hills - 3

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Favorite Bear Mountain Peak
Intermediate/Difficult

Bear Mountain

5.4 mi 8.7 km 1,549' Up 472.12 m Up 1,548' Down 471.96 m Down

Salisbury, CT
Favorite Coming down from Cobble Mountain.
Difficult

Macedonia Ridge Trail

6.4 mi 10.3 km 1,592' Up 485.14 m Up 1,586' Down 483.51 m Down

Kent, 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 1,110' Up 338.19 m Up 1,107' Down 337.29 m Down

Canaan, CT

Trails in Litchfield Hills - 145

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1.2 mi 2.0 km #1Lion's Head Trail
Difficult
Canaan, CT
Difficult
Canaan, CT
1.7 mi 2.7 km #2Pomperaug Trail - Blue
Difficult
Southbury, CT
Difficult
Southbury, CT
0.4 mi 0.7 km #3Quarry Trail
Difficult
West Torrington, CT
Difficult
West Torrington, CT
1.7 mi 2.8 km #4Crest Trail - Blue/White
Difficult
Southbury, CT
Difficult
Southbury, CT
18.1 mi 29.1 km #5Quinnipiac Trail
Intermediate/Difficult
Cheshire Village, CT
Intermediate/Difficult
Cheshire Village, CT
51.6 mi 83.1 km #6AT: AMC - Connecticut Chapter (CT/NY)
Intermediate
Sherman, CT
Intermediate
Sherman, CT
1.4 mi 2.3 km #7Roaring Brook Trail
Intermediate
Cheshire, CT
Intermediate
Cheshire, CT
2.7 mi 4.4 km #8Mt. Frissell Trail
Difficult
Canaan, CT
Difficult
Canaan, CT
1.8 mi 3.0 km #9Mattatuck Trail
Intermediate
Litchfield, CT
Intermediate
Litchfield, CT
2.0 mi 3.2 km #10Bee Brook Loop
Intermediate
New Preston, CT
Intermediate
New Preston, CT
0.7 mi 1.1 km #11Granniss Pond Trail
Intermediate
Litchfield, CT
Intermediate
Litchfield, CT
1.8 mi 2.8 km #12Miller Trail - Blue
Intermediate
Southbury, CT
Intermediate
Southbury, CT
0.5 mi 0.8 km #13Campbell Falls Trail (Yellow)
Easy
Canaan, CT
Easy
Canaan, CT
0.5 mi 0.9 km #14Tree ID Trail
Easy/Intermediate
Bristol, CT
Easy/Intermediate
Bristol, CT
26.8 mi 43.1 km #15Mattatuck Trail
Intermediate
Litchfield, CT
Intermediate
Litchfield, CT
1.7 mi 2.8 km #16Pinnacle Trail
Intermediate
New Preston, CT
Intermediate
New Preston, CT
4.0 mi 6.4 km #17Iron Trail
Difficult
Canaan, CT
Difficult
Canaan, CT
1.9 mi 3.0 km #18Under Mountain Trail
Intermediate
Canaan, CT
Intermediate
Canaan, CT
0.8 mi 1.3 km #19Cobble Mountain Trail (White)
Difficult
Kent, CT
Difficult
Kent, CT
1.4 mi 2.3 km #20Stone Man Mountain Trail
Intermediate
Canaan, CT
Intermediate
Canaan, CT

Photos of Litchfield Hills - 70

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Roaring Brook Falls
Nov 11, 2015 near Prospect, CT
Hiking Along Spruce Brook
Jul 8, 2019 near Naugatuck, CT
Hay field from Meeker Trail
May 29, 2020 near New Pre…, CT
Coming down from Cobble Mountain.
Jul 23, 2020 near Kent, 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