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Litchfield Hills

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Gems in Litchfield Hills - 6

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gem Favorite Bear Mountain Peak

Bear Mountain

(1) Salisbury, CT
gem 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.

Rand's View

(1) Salisbury, CT
gem Favorite Great views from the tower.

Haystack Mountain Tower

(1) Canaan, CT
gem Favorite Kent Falls from the base

Kent Falls

(1) Kent, CT
gem Favorite Beckley Iron Furnace

Beckley Iron Furnace

(1) Canaan, CT
gem Favorite Roaring Brook Falls

Roaring Brook Falls

(1) Prospect, CT

Recommended Routes in Litchfield Hills - 3

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Favorite Lower Viewpoint about 0.2 mi from the 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 Stunning views 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

Litchfield Hills Running

  • 363 Miles 584 Kilometers of Trail
  • 3 Recommended Routes
  • 6 Gems Gems
  • 65 Easy Trails Easy Trails
  • 79 Intermediate Trails Intermediate Trails
  • 17 Difficult Trails Difficult Trails
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Areas Within Litchfield Hills

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Trails in Litchfield Hills - 158

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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
1.0 mi 1.6 km #5Nepaug Dam Trail
Easy
Collinsville, CT
Easy
Collinsville, CT
18.1 mi 29.1 km #6Quinnipiac Trail
Intermediate/Difficult
Cheshire Village, CT
Intermediate/Difficult
Cheshire Village, CT
51.6 mi 83.1 km #7AT: AMC - Connecticut Chapter (CT/NY)
Intermediate
Sherman, CT
Intermediate
Sherman, CT
1.3 mi 2.1 km #8Roaring Brook Trail
Intermediate/Difficult
Cheshire, CT
Intermediate/Difficult
Cheshire, CT
2.7 mi 4.4 km #9Mt. Frissell Trail
Difficult
Canaan, CT
Difficult
Canaan, CT
1.8 mi 3.0 km #10Mattatuck Trail
Intermediate
Litchfield, CT
Intermediate
Litchfield, CT

Photos of Litchfield Hills - 89

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Roaring Brook Falls
Nov 11, 2015 near Prospect, CT
Lower Viewpoint about 0.2 mi from the peak.
Nov 12, 2020 near Salisbury, CT
Great views from the tower.
Jan 14, 2021 near Canaan, CT
Hay field from Meeker Trail
May 29, 2020 near New Pre…, CT
View from the peak of Bear Mountain on a beautiful day!
Nov 17, 2020 near Salisbury, CT
Stunning views from Cobble Mountain
Dec 30, 2017 near Kent, CT
Cobble Mountain view
Dec 30, 2017 near Kent, CT
Beckley Iron Furnace
Mar 21, 2021 near Canaan, CT