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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

(2) Salisbury, CT
gem Favorite Rand's View, October 3, 2020

Rand's View

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

Haystack Mountain Tower

(1) Canaan, CT
gem Favorite Beckley Iron Furnace

Beckley Iron Furnace

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

Kent Falls

(1) Kent, CT
gem Favorite Roaring Brook Falls

Roaring Brook Falls

(1) Prospect, CT

Recommended Routes in Litchfield Hills - 4

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RECOMMENDED ROUTE
Favorite Lower Viewpoint about 0.2 mi from the peak.
Intermediate/Difficult 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
Explore in 3D
RECOMMENDED ROUTE
Favorite Stunning views from Cobble Mountain
Difficult 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
Explore in 3D
RECOMMENDED ROUTE
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.
Intermediate/Difficult Intermediate/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
Explore in 3D
RECOMMENDED ROUTE
Favorite The Black Rock footbridge.
Intermediate Intermediate

Black Rock Loop

1.1 mi 1.8 km • 335' Up 102.24 m Up • 334' Down 101.83 m Down

Thomaston, CT
Explore in 3D

Litchfield Hills Hiking

  • 305 Miles 492 Kilometers of Trail
  • 4 Recommended Routes
  • 6 Gems Gems
  • 83 Easy Trails Easy Trails
  • 109 Intermediate Trails Intermediate Trails
  • 20 Difficult Trails Difficult Trails
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Areas Within Litchfield Hills

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Trails in Litchfield Hills - 208

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1.2 mi 2.0 km #1Lion's Head Trail
Difficult Difficult
Canaan, CT
Difficult Difficult
Canaan, CT 2 
1.7 mi 2.7 km #2Pomperaug Trail - Blue
Difficult Difficult
Southbury, CT
Difficult Difficult
Southbury, CT 2 
1.0 mi 1.6 km #3Nepaug Dam Trail
Easy Easy
Collinsville, CT
Easy Easy
Collinsville, CT 1 
1.7 mi 2.8 km #4Crest Trail - Blue/White
Difficult Difficult
Southbury, CT
Difficult Difficult
Southbury, CT 1 
0.4 mi 0.7 km #5Quarry Trail
Difficult Difficult
West Torrington, CT
Difficult Difficult
West Torrington, CT 1 
2.5 mi 4.1 km #6Pine Knob Loop Trail
Intermediate Intermediate
Kent, CT
Intermediate Intermediate
Kent, CT 3 
18.1 mi 29.1 km #7Quinnipiac Trail
Intermediate/Difficult Intermediate/Difficult
Cheshire Village, CT
Intermediate/Difficult Intermediate/Difficult
Cheshire Village, CT 4 
3.7 mi 5.9 km #8Scoville Reservoir Trail
Easy Easy
Wolcott, CT
Easy Easy
Wolcott, CT 2 
3.8 mi 6.1 km #9Steep Rock Loop
Intermediate Intermediate
New Preston, CT
Intermediate Intermediate
New Preston, CT 3 
1.8 mi 3.0 km #10Mattatuck Trail
Intermediate Intermediate
Litchfield, CT
Intermediate Intermediate
Litchfield, CT 4 

Photos of Litchfield Hills - 97

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Roaring Brook Falls
Nov 11, 2015 near Prospect, CT
Stunning views from Cobble Mountain
Dec 30, 2017 near Kent, CT
Hiking Along Spruce Brook
Jul 8, 2019 near Naugatuck, CT
Bear Mountain Peak
Jul 8, 2019 near Salisbury, CT
Hay field from Meeker Trail
May 29, 2020 near New Pre…, CT
Lower Viewpoint about 0.2 mi from the peak.
Nov 12, 2020 near Salisbury, CT
View from the peak of Bear Mountain on a beautiful day!
Nov 17, 2020 near Salisbury, CT
Great views from the tower.
Jan 14, 2021 near Canaan, CT
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