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Hiking Trails Over 20 km in Connecticut

The directory currently contains 22 quality-checked routes matching this guide in Connecticut. Their average mapped distance is 67.3 km and average recorded ascent is 1,006 m (3,301 ft); the longest route in the set is 327 km.

This subset represents 2% of the 910 quality-checked routes in Connecticut. Its average distance is 67.3 km, compared with 3.6 km across the full local set. Average recorded ascent is 1,006 m (3,301 ft), versus 74 m (243 ft) for all quality-checked routes in the same area.

Every route in this set is at least 20 km long. Whether it is normally completed in one day or in stages is not inferred from distance alone. Within this set, 0 routes (0%) are rated easy, 22 (100%) are rated hard or expert, and 0 (0%) 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

Choose by the details

How do these routes differ?

A closer look at the first 6 routes in this page’s default ordering. These comparisons describe this sample, not the entire destination or a field-tested recommendation.

Shortest mapped distance in this sample

45.9 km

Nipmuck Trail

Compare the climbing too; shortest does not necessarily mean easiest.

Lowest recorded ascent in this sample

633 m

Nipmuck Trail

6 of 6 have ascent data. Missing measurements are excluded.

Return logistics

0 recorded loops

Check start and finish for every option. An unknown shape does not mean a loop, and a loop does not establish access to its start.

Plan the return journey →

Distances follow stored route lines; ascent and time are estimates. Current access, surface and technical difficulty need separate checks. How to turn a comparison into a shortlist.

Trails

Expert

Appalachian Trail

Connecticut · United States

Distance
80.6 km
/ 50.1 mi
Elevation gain
2,207 m
Typical duration
22 hr
  • Mountain
  • Waymarked route
  • Long-distance path
Expert

Mattabesett Trail

Connecticut · United States

Distance
95.2 km
/ 59.2 mi
Elevation gain
1,205 m
Typical duration
24 hr
  • Mountain
  • Forest
  • Waymarked route
Expert

Metacomet Trail

Connecticut · United States

Distance
95.1 km
/ 59.1 mi
Elevation gain
1,550 m
Typical duration
24 hr
  • Mountain
  • Forest
  • Waymarked route
Expert

Metacomet - Monadnock Trail

Connecticut · United States

Distance
183 km
/ 114 mi
Elevation gain
2,956 m
Typical duration
47 hr
  • Mountain
  • Waymarked route
  • Long-distance path
Yale-Myers Forest Research Site off Nipmuck Trail.
Expert

Nipmuck Trail

Connecticut · United States

Distance
45.9 km
/ 28.5 mi
Elevation gain
633 m
Typical duration
11 hr
  • Mountain
  • Forest
  • Waymarked route
Expert

Mattatuck Trail

Connecticut · United States

Distance
65.2 km
/ 40.5 mi
Elevation gain
1,162 m
Typical duration
16 hr
  • Mountain
  • Waymarked route
  • Long-distance path
Expert

North South Trail

Connecticut · United States

Distance
121 km
/ 75.4 mi
Elevation gain
674 m
Typical duration
29 hr
  • Mountain
  • Waymarked route
  • Long-distance path
Expert

Tunxis Trail

Connecticut · United States

Distance
72.4 km
/ 45.0 mi
Elevation gain
1,464 m
Typical duration
19 hr
  • Mountain
  • Waymarked route
  • Long-distance path
Expert

Shenipsit Trail

Connecticut · United States

Distance
73.7 km
/ 45.8 mi
Elevation gain
991 m
Typical duration
18 hr
  • Mountain
  • Waymarked route
  • Long-distance path
Expert

Mohawk Trail

Connecticut · United States

Distance
35.8 km
/ 22.2 mi
Elevation gain
1,228 m
Typical duration
9 hr 55 min
  • Mountain
  • Waymarked route
Round Hill Brook, Webb Mountain Park, Paugussett Trail, Monroe, CT.
Hard

Paugussett Trail

Connecticut · United States

Distance
20.9 km
/ 13.0 mi
Elevation gain
508 m
Typical duration
5 hr 17 min
  • River
  • Forest
  • Waymarked route
Log bridge, Pachaug Trail - Wiclcabouet Marsh, Voluntown, CT
Hard

Pachaug Trail

Connecticut · United States

Distance
34.7 km
/ 21.6 mi
Elevation gain
433 m
Typical duration
8 hr 28 min
  • Mountain
  • Waymarked route
Expert

Quinnipiac Trail

Connecticut · United States

Distance
31.5 km
/ 19.6 mi
Elevation gain
848 m
Typical duration
8 hr 20 min
  • Forest
  • Waymarked route
Menunkatuck Blue-Blazed (CFPA) Trail. Vernal pond along the Menunkatuck Trail in the Timberlands near the Iron Stream. Timberlands is forested preserved open space owned by the Town of Guilford Connecticut and managed by the Town's Conserva
Hard

Menunkatuck Trail

Connecticut · United States

Distance
25.8 km
/ 16.0 mi
Elevation gain
277 m
Typical duration
6 hr 7 min
  • Forest
  • Waymarked route
Hard

Ives Trail Greenway

Connecticut · United States

Distance
21.5 km
/ 13.4 mi
Elevation gain
712 m
Typical duration
5 hr 45 min
  • Waymarked route
Natchaug Trail sign on Connecticut Route 44. Entrance to northern sections.
Hard

Natchaug Trail

Connecticut · United States

Distance
27.9 km
/ 17.3 mi
Elevation gain
405 m
Typical duration
6 hr 48 min
  • Waymarked route
Hard

Richard H. Goodwin Trail

Connecticut · United States

Distance
21.6 km
/ 13.5 mi
Elevation gain
316 m
Typical duration
5 hr 11 min
  • Waymarked route
The blue girder bridge bearing the Tilcon logo carries the Branford Steam Railroad over U.S. Route 1 (Post Road) in Branford, Connecticut. This view is looking west.
Hard

The Branford Trail

Connecticut · United States

Distance
26.9 km
/ 16.7 mi
Elevation gain
201 m
Typical duration
6 hr 16 min
  • Waymarked route
Hard

Hockanum River Linear Park

Connecticut · United States

Distance
31.2 km
/ 19.4 mi
Elevation gain
146 m
Typical duration
7 hr 12 min
  • River
Hard

Mission 22 Trail

Connecticut · United States

Distance
22.7 km
/ 14.1 mi
Elevation gain
515 m
Typical duration
5 hr 44 min
Hard

Deer Pond Farm Trails

Connecticut · United States

Distance
20.5 km
/ 12.8 mi
Elevation gain
693 m
Typical duration
5 hr 29 min

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
Appalachian TrailConnecticut80.6 km2,207 m22 hrExpertApril to October
Mattabesett TrailConnecticut95.2 km1,205 m24 hrExpertApril to October
Metacomet TrailConnecticut95.1 km1,550 m24 hrExpertApril to October
New England National Scenic TrailConnecticut327 km3,016 m82 hrExpertApril to October
Metacomet - Monadnock TrailConnecticut183 km2,956 m47 hrExpertApril to October
Nipmuck TrailConnecticut45.9 km633 m11 hrExpertApril to October
Mattatuck TrailConnecticut65.2 km1,162 m16 hrExpertApril to October
North South TrailConnecticut121 km674 m29 hrExpertApril to October
Tunxis TrailConnecticut72.4 km1,464 m19 hrExpertApril to October
Shenipsit TrailConnecticut73.7 km991 m18 hrExpertApril to October

Appalachian Trail, Mattabesett Trail, Metacomet 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

Plan with more confidence

All planning articles →

Choosing a route

How to choose a hike beyond the difficulty label

Compare distance, climbing, route shape and missing information to build a shortlist that fits your day.

Read article →

Understanding the map

Read an elevation profile without misreading the climb

Understand total ascent, net height change, profile scale and the section breakdown on each mapped route.

Read article →

Planning your day

Build a hiking time plan with room for your own pace

Separate moving time, climbing allowance and stops, then explore how changing your assumptions changes the plan.

Read article →

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