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Moderate Hiking Trails in Connecticut

The directory currently contains 318 quality-checked routes matching this guide in Connecticut. Their average mapped distance is 2.7 km and average recorded ascent is 93 m (305 ft); the longest route in the set is 15.0 km.

This subset represents 35% of the 910 quality-checked routes in Connecticut. Its average distance is 2.7 km, compared with 3.6 km across the full local set.

Every route in this set is rated moderate by the directory’s distance-and-elevation model. Technical terrain and live conditions are not part of that rating. Within this set, 0 routes (0%) are rated easy, 0 (0%) are rated hard or expert, and 63 (20%) are recorded as loops. Ratings are computed from available distance and elevation data and do not establish current terrain or access.

Data refreshed September 2026

Trails

Moderate

North Summit Trail

Connecticut · United States

Distance
1.3 km
/ 0.8 mi
Elevation gain
10 m
Typical duration
17 min
  • Mountain
  • Summit push
  • Panoramic viewpoint
Whitestone Cliffs Trail. Blue-Blazed CFPA "loop" foot path in Mattatuck State Forest. Whitestone Cliffs Trail. Blue-Blazed CFPA "loop" foot path in Mattatuck State Forest. Whitestone Cliffs Trail head sign on Spruce Brook Road / Mt Tobe.
Moderate

Whitestone Cliffs Trail

Connecticut · United States

Distance
2.2 km
/ 1.4 mi
Elevation gain
84 m
Typical duration
35 min
  • Coastal
  • Waymarked route
Heavy snow remained at stations along Metro-North Railroad's Waterbury Branch, preventing normal service the morning of Monday, Feb. 11, 2013.
Moderate

Beacon Falls Yellow Trail

Connecticut · United States

Distance
2.8 km
/ 1.7 mi
Elevation gain
153 m
Typical duration
49 min
  • Waterfall
  • Lake
  • Waymarked route
Moderate

Lookout Mountain Trail

Connecticut · United States

Distance
1.7 km
/ 1.1 mi
Elevation gain
84 m
Typical duration
29 min
  • Mountain
  • Panoramic viewpoint
  • Waymarked route
Jericho Blue-Blazed Trail. Ruins of Bridge at end of Sheffield Street, Waterbury. Trailhead for Hancock Brook Trail.
Moderate

Hancock Brook Trail

Connecticut · United States

Distance
4.2 km
/ 2.6 mi
Elevation gain
212 m
Typical duration
1 hr 11 min
  • River
  • Waymarked route
Salmon River Trail Comstock Covered Bridge from state forest parking lot side.
Moderate

Salmon River Trail

Connecticut · United States

Distance
7.5 km
/ 4.6 mi
Elevation gain
136 m
Typical duration
1 hr 45 min
  • River
  • Forest
  • Waymarked route
Moderate

Bald Mountain Red Trail

Connecticut · United States

Distance
4.2 km
/ 2.6 mi
Elevation gain
192 m
Typical duration
1 hr 10 min
  • Mountain
  • Waymarked route
Moderate

Nipmuck Trail - East Branch

Connecticut · United States

Distance
10.5 km
/ 6.5 mi
Elevation gain
187 m
Typical duration
2 hr 28 min
  • Waymarked route
Moderate

Nipmuck Trail - West Branch

Connecticut · United States

Distance
8.3 km
/ 5.2 mi
Elevation gain
144 m
Typical duration
1 hr 57 min
  • Waymarked route
Moderate

Regicides Trail

Connecticut · United States

Distance
11.0 km
/ 6.9 mi
Elevation gain
243 m
Typical duration
2 hr 40 min
  • Waymarked route
Moderate

Bald Mountain White Trail

Connecticut · United States

Distance
1.5 km
/ 0.9 mi
Elevation gain
85 m
Typical duration
26 min
  • Mountain
  • Waymarked route
Moderate

Birch Mountain Trail

Connecticut · United States

Distance
1.4 km
/ 0.9 mi
Elevation gain
14 m
Typical duration
19 min
  • Mountain
  • Waymarked route
Moderate

Bald Mountain Green Trail

Connecticut · United States

Distance
0.9 km
/ 0.6 mi
Elevation gain
22 m
Typical duration
14 min
  • Mountain
  • Waymarked route
Moderate

Baldy Ridge Trail

Connecticut · United States

Distance
0.6 km
/ 0.4 mi
Elevation gain
31 m
Typical duration
10 min
  • Mountain
  • Waymarked route
Moderate

Vista Trail

Connecticut · United States

Distance
2.5 km
/ 1.6 mi
Elevation gain
157 m
Typical duration
46 min
  • Panoramic viewpoint
  • Waymarked route
Dr. Andrew Castle House , Woodbridge, Connecticut.
Moderate

Naugatuck Trail (Woodbridge)

Connecticut · United States

Distance
12.7 km
/ 7.9 mi
Elevation gain
218 m
Typical duration
2 hr 58 min
  • Waymarked route
Moderate

Pomperaug Trail

Connecticut · United States

Distance
6.6 km
/ 4.1 mi
Elevation gain
325 m
Typical duration
1 hr 52 min
  • Forest
  • Waymarked route
Belden Dam on the French River in June 2021
Moderate

Quinebaug River Trail

Connecticut · United States

Distance
9.1 km
/ 5.7 mi
Elevation gain
58 m
Typical duration
1 hr 59 min
  • River
  • Waymarked route
The ravine of Roaring Brook Falls.
Moderate

Roaring Brook Falls Trail

Connecticut · United States

Distance
0.9 km
/ 0.6 mi
Elevation gain
115 m
Typical duration
21 min
  • Waterfall
  • Lake
  • River
Jericho Blue-Blazed Trail. Ferns on ledges on climb up ravine at mid-point in Jericho Trail.
Moderate

Jericho Trail

Connecticut · United States

Distance
5.2 km
/ 3.2 mi
Elevation gain
312 m
Typical duration
1 hr 33 min
  • Waymarked route
Moderate

Summit Trail

Connecticut · United States

Distance
0.5 km
/ 0.3 mi
Elevation gain
23 m
Typical duration
8 min
  • Mountain
  • Summit push
  • Panoramic viewpoint
Moderate

Ravine Trail

Connecticut · United States

Distance
1.4 km
/ 0.8 mi
Elevation gain
41 m
Typical duration
21 min
  • Canyon and gorge
  • Waymarked route
One of many Chatfield Trail rock caves (and other rock formations) hikers can squeeze through.
Moderate

Chatfield Trail

Connecticut · United States

Distance
6.9 km
/ 4.3 mi
Elevation gain
168 m
Typical duration
1 hr 41 min
  • Forest
  • Waymarked route
Lake Compounce Amusement Park Non-Ski Lift High Point on Tunxis Trail in Bristol, CT.
Moderate

Compounce Connector Trail

Connecticut · United States

Distance
0.8 km
/ 0.5 mi
Elevation gain
141 m
Typical duration
22 min
  • Waymarked route
Moderate

Elliott Bronson Trail

Connecticut · United States

Distance
3.1 km
/ 1.9 mi
Elevation gain
174 m
Typical duration
54 min
  • Waymarked route
Housatonic Range Blue-Blazed Trail. Blue-Blazed CFPA linear foot path from Candlewood Mountain in New Milford and to Gaylordsville Cemetary in Gaylordsville. Housatonic Range CFPA Blue-Blazed Trail in New Milford. Housatonic Range Trail (AK
Moderate

Housatonic Range Trail

Connecticut · United States

Distance
4.9 km
/ 3.0 mi
Elevation gain
360 m
Typical duration
1 hr 34 min
  • Waymarked route
Tri-state boundary marker on the Mount Frissell Trail in Mount Washington State Forest marks Connecticut's northwest corner even though Connecticut is just "graffiti' on the granite (only Massachusetts and New York are engraved in the stone
Moderate

Mt. Frissell

Connecticut · United States

Distance
2.9 km
/ 1.8 mi
Elevation gain
253 m
Typical duration
59 min
  • Waymarked route
Moderate

Robet Ross Trail

Connecticut · United States

Distance
3.6 km
/ 2.2 mi
Elevation gain
260 m
Typical duration
1 hr 8 min
  • Waymarked route
Moderate

Steep Climb Trail

Connecticut · United States

Distance
1.1 km
/ 0.7 mi
Elevation gain
190 m
Typical duration
31 min
  • Waymarked route
Moderate

Zoar Trail

Connecticut · United States

Distance
10.2 km
/ 6.3 mi
Elevation gain
341 m
Typical duration
2 hr 38 min
  • Waymarked route
Moderate

Blue Trail

Connecticut · United States

Distance
1.5 km
/ 1.0 mi
Elevation gain
54 m
Typical duration
24 min
  • Waymarked route
Moderate

Blue-White-Dot Trail

Connecticut · United States

Distance
1.1 km
/ 0.7 mi
Elevation gain
20 m
Typical duration
15 min
  • Waymarked route
View from Kettletown State Park's Crest Trail of the Housatonic River's Lake Zoar looking south towards Oxford.
Moderate

Crest Trail

Connecticut · United States

Distance
3.2 km
/ 2.0 mi
Elevation gain
117 m
Typical duration
50 min
  • Waymarked route
Moderate

Dan Beard Trail

Connecticut · United States

Distance
1.5 km
/ 0.9 mi
Elevation gain
43 m
Typical duration
23 min
  • Waymarked route
Moderate

Delia Trail

Connecticut · United States

Distance
2.0 km
/ 1.2 mi
Elevation gain
75 m
Typical duration
32 min
  • Waymarked route
Moderate

Fire Trail

Connecticut · United States

Distance
0.9 km
/ 0.6 mi
Elevation gain
75 m
Typical duration
18 min
  • Waymarked route
Moderate

Former Tunxis Trail

Connecticut · United States

Distance
1.6 km
/ 1.0 mi
Elevation gain
35 m
Typical duration
24 min
  • Waymarked route
Moderate

Hardwood Trail

Connecticut · United States

Distance
1.9 km
/ 1.2 mi
Elevation gain
30 m
Typical duration
27 min
  • Waymarked route
Haystack Mountain Tower, 43 North St. Norfolk
Moderate

Haystack Tower Loop Trail

Connecticut · United States

Distance
2.6 km
/ 1.6 mi
Elevation gain
135 m
Typical duration
44 min
  • Waymarked route
Moderate

Highland Trail

Connecticut · United States

Distance
1.8 km
/ 1.1 mi
Elevation gain
62 m
Typical duration
28 min
  • Waymarked route
Holiday House was a retreat for young working women from New York City operated by the St. Bartholomew's Episcopal Church and was the reason for the "Valley" station along the Shepaug Railroad. These steps are part of the remains of the ret
Moderate

Holiday House Loop

Connecticut · United States

Distance
1.5 km
/ 0.9 mi
Elevation gain
60 m
Typical duration
24 min
  • Waymarked route
Moderate

Joshua's Trust

Connecticut · United States

Distance
1.4 km
/ 0.9 mi
Elevation gain
43 m
Typical duration
21 min
  • Waymarked route
Moderate

Knapp Way

Connecticut · United States

Distance
1.3 km
/ 0.8 mi
Elevation gain
31 m
Typical duration
19 min
  • Waymarked route
Narragansett Trail's Lantern Hill view of the Mashantucket Pequots Foxwoods Casino Resort. This is an image of a place or building that is listed on the National Register of Historic Places in the United States of America . Its reference nu
Moderate

Lantern Hill Trail

Connecticut · United States

Distance
2.1 km
/ 1.3 mi
Elevation gain
144 m
Typical duration
40 min
  • Waymarked route
Moderate

Lillinoah Trail

Connecticut · United States

Distance
9.0 km
/ 5.6 mi
Elevation gain
310 m
Typical duration
2 hr 20 min
  • Waymarked route

The shortlist, side by side

The ten highest scoring routes on this page, so you can compare effort before opening any of them.

Distance, ascent, walking time and difficulty for the top routes
RouteDistanceAscentTimeDifficultyBest season
North Summit TrailConnecticut1.3 km10 m17 minModerateApril to October
Whitestone Cliffs TrailConnecticut2.2 km84 m35 minModerateApril to October
Beacon Falls Yellow TrailConnecticut2.8 km153 m49 minModerateApril to October
Lookout Mountain TrailConnecticut1.7 km84 m29 minModerateApril to October
Hancock Brook TrailConnecticut4.2 km212 m1 hr 11 minModerateApril to October
Salmon River TrailConnecticut7.5 km136 m1 hr 45 minModerateApril to October
Bald Mountain Red TrailConnecticut4.2 km192 m1 hr 10 minModerateApril to October
Ives Trail Greenway AlternativeConnecticut2.5 km159 m45 minModerateApril to October
Nipmuck Trail - East BranchConnecticut10.5 km187 m2 hr 28 minModerateApril to October
Nipmuck Trail - West BranchConnecticut8.3 km144 m1 hr 57 minModerateApril to October

North Summit Trail, Whitestone Cliffs Trail, Beacon Falls Yellow Trail currently rank highest in this filtered set according to the directory score. Open an individual route to inspect its mapped line, elevation profile, data source and planning caveats. Check live access, conditions and local rules with an official source before travelling.

Frequently asked questions

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