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Connecticut

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1,239 mi 1,994 km of trail 22 Recommended Routes

Easy Trails 267 Trails Intermediate Trails 335 Trails Hard Trails 59 Trails
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Recommended Routes in Connecticut - 19

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Favorite Castle Craig on a chilly fall day
Intermediate

Castle Craig

2.8 mi 4.5 km 644' Up 196.41 m Up 644' Down 196.37 m Down

Meriden, 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 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 The basic condition of the trail looping around the pond is low and close to the water.
Intermediate

Green Falls Narragansett Loop

3.0 mi 4.9 km 186' Up 56.69 m Up 185' Down 56.49 m Down

Preston…, CT
Favorite No Photos
Difficult

Shenipsit Trail

50.8 mi 81.7 km 4,117' Up 1255.01 m Up 4,035' Down 1229.72 m Down

East Ha…, CT
Favorite Awesome light on one of the easier ascents on Yellow Trail - Pine Mountain.
Intermediate/Difficult

Pine Mountain

4.1 mi 6.6 km 677' Up 206.32 m Up 677' Down 206.2 m Down

Ridgefield, CT
Favorite Zoar Trail - frozen waterfall on winter outing.
Intermediate

Zoar Trail

6.4 mi 10.2 km 1,105' Up 336.9 m Up 1,105' Down 336.9 m Down

Oxford, CT
Favorite Colorful shoreline
Intermediate/Difficult

West Rock Ridge Loop

7.9 mi 12.7 km 785' Up 239.13 m Up 772' Down 235.3 m Down

New Haven, CT

Trails in Connecticut - 639

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10.7 mi 17.3 km #1Saugatuck Trail
Difficult
Easton, CT
Difficult
Easton, CT
2.0 mi 3.2 km #2Norwalk River Valley Trail
Easy
Wilton, CT
Easy
Wilton, CT
1.2 mi 2.0 km #3Lion's Head Trail
Difficult
Canaan, CT
Difficult
Canaan, CT
1.7 mi 2.7 km #4Pomperaug Trail - Blue
Difficult
Southbury, CT
Difficult
Southbury, CT
11.5 mi 18.5 km #5Naugatuck (Blue) Trail
Intermediate/Difficult
Woodbridge, CT
Intermediate/Difficult
Woodbridge, CT
4.4 mi 7.1 km #6Shelton Lakes Recreation Path
Easy
Shelton, CT
Easy
Shelton, CT
0.5 mi 0.7 km #7Laurel Grove Brook Trail
Intermediate
Middletown, CT
Intermediate
Middletown, CT
0.5 mi 0.9 km #8Winslow Dog Park Outer Loop
Easy
Westport, CT
Easy
Westport, CT
2.2 mi 3.6 km #9Yellow Trail
Intermediate
Hamden, CT
Intermediate
Hamden, CT
0.4 mi 0.7 km #10Sidecut Trail
Intermediate
Bethel, CT
Intermediate
Bethel, CT
0.4 mi 0.7 km #11Quarry Trail
Difficult
West Torrington, CT
Difficult
West Torrington, CT
1.4 mi 2.3 km #12Green Square Trail
Difficult
Guilford, CT
Difficult
Guilford, CT
1.7 mi 2.8 km #13Crest Trail - Blue/White
Difficult
Southbury, CT
Difficult
Southbury, CT
0.7 mi 1.2 km #14Meadow Trail (Yellow)
Intermediate
Woodbridge, CT
Intermediate
Woodbridge, CT
0.4 mi 0.7 km #15Red/White Trail
Easy/Intermediate
Woodbridge, CT
Easy/Intermediate
Woodbridge, CT
0.3 mi 0.5 km #16Red Trail
Intermediate/Difficult
Guilford, CT
Intermediate/Difficult
Guilford, CT
0.3 mi 0.4 km #17Orange Trail
Intermediate
Guilford, CT
Intermediate
Guilford, CT
0.5 mi 0.7 km #18Goss Fields Trail
Easy
Guilford, CT
Easy
Guilford, CT
5.1 mi 8.3 km #19Blue Trail
Difficult
Hamden, CT
Difficult
Hamden, CT
2.6 mi 4.2 km #20Red Trail
Difficult
Easton, CT
Difficult
Easton, CT

Photos of Connecticut - 286

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Roaring Brook Falls
Nov 11, 2015 near Prospect, CT
View Point
May 15, 2019 near Meriden, CT
Castle Craig on a chilly fall day
Nov 12, 2018 near Meriden, CT
Late season snow around Spaulding Pond
Apr 2, 2018 near Norwich, CT
Hiking Along Spruce Brook
Jul 8, 2019 near Naugatuck, CT
Rewarding view after a steep climb!
Jan 7, 2016 near Manchester, CT
Hay field from Meeker Trail
May 29, 2020 near New Pre…, CT
Mossy doubletrack running along Sap Brook.
Jan 7, 2015 near Georgetown, CT