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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 - 22

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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 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 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 The course is marked with the Shenipsit sprinkler flags
Difficult

Soapstone Mountain Trail Race

13.8 mi 22.2 km 1,815' Up 553.27 m Up 1,836' Down 559.49 m Down

Staffor…, 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 The course is marked with the Shenipsit sprinkler flags
Intermediate

Jerry Stage 6K

3.8 mi 6.0 km 511' Up 155.77 m Up 537' Down 163.61 m Down

Staffor…, CT
Favorite Pine Mountain Lookout.
Intermediate/Difficult

Pine Mountain

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

Ridgefield, 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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Mmmmmm... New England is nice.
Dec 26, 2015 near Easton, CT
Roaring Brook Falls
Nov 11, 2015 near Prospect, CT
A nice little section of the Saugatuck Trail.
Dec 29, 2015 near Easton, CT
Castle Craig on a chilly fall day
Nov 12, 2018 near Meriden, CT
A nice downhill section on the Saugatuck Trail.
Dec 29, 2015 near Georgetown, CT
Late season snow around Spaulding Pond
Apr 2, 2018 near Norwich, CT
Did I mention that this part of the country is rocky?
Dec 26, 2015 near Easton, CT
Rewarding view after a steep climb!
Jan 7, 2016 near Manchester, CT