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Best Mountain Hikes near Waterbury

The directory currently contains 15 quality-checked routes matching this guide near Waterbury. Their average mapped distance is 31.0 km and average recorded ascent is 654 m (2,146 ft); the longest route in the set is 95.2 km.

This subset represents 8% of the 183 quality-checked routes near Waterbury. Its average distance is 31.0 km, compared with 5.4 km across the full local set. Average recorded ascent is 654 m (2,146 ft), versus 125 m (410 ft) for all quality-checked routes in the same area.

These routes carry the mountain tag. Their measured distance and ascent are shown separately so the label is not used as a proxy for difficulty. Within this set, 0 routes (0%) are rated easy, 6 (40%) are rated hard or expert, and 2 (13%) 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

1.3 km

North Summit Trail

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

Lowest recorded ascent in this sample

10 m

North Summit 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

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

Connecticut · United States

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

Connecticut · United States

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

Connecticut · United States

Distance
1.3 km
/ 0.8 mi
Elevation gain
10 m
Typical duration
17 min
  • Mountain
  • Summit push
  • Panoramic viewpoint
Expert

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

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

Connecticut · United States

Distance
35.8 km
/ 22.2 mi
Elevation gain
1,228 m
Typical duration
9 hr 55 min
  • Mountain
  • Waymarked route
Moderate

Connecticut · United States

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

Connecticut · United States

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

Connecticut · United States

Distance
4.7 km
/ 2.9 mi
Elevation gain
169 m
Typical duration
1 hr 13 min
  • Mountain
  • Waymarked route
Moderate

Connecticut · United States

Distance
1.0 km
/ 0.6 mi
Elevation gain
28 m
Typical duration
15 min
  • Mountain
  • Waymarked route
Moderate

Connecticut · United States

Distance
0.9 km
/ 0.5 mi
Elevation gain
21 m
Typical duration
13 min
  • Mountain
  • Summit push
  • Panoramic viewpoint
View from Cobble Mountain summit with New York State's Catskill Mountains in background. In Connecticut's Macedonia Brook State Park.
Moderate

Connecticut · United States

Distance
1.4 km
/ 0.9 mi
Elevation gain
194 m
Typical duration
35 min
  • Mountain
  • Waymarked route
View from Cobble Mountain summit with New York State's Catskill Mountains in background. In Connecticut's Macedonia Brook State Park.
Moderate

Connecticut · United States

Distance
10.3 km
/ 6.4 mi
Elevation gain
513 m
Typical duration
2 hr 55 min
  • Mountain
  • 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
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
North Summit TrailConnecticut1.3 km10 m17 minModerateApril to October
Mattatuck TrailConnecticut65.2 km1,162 m16 hrExpertApril to October
Tunxis TrailConnecticut72.4 km1,464 m19 hrExpertApril to October
Mohawk TrailConnecticut35.8 km1,228 m9 hr 55 minExpertApril to October
Mountain Spring Nature TrailConnecticut0.5 km0 m6 minModerateApril to October
Baldy Ridge TrailConnecticut0.6 km31 m10 minModerateApril to October
Summit TrailConnecticut0.5 km23 m8 minModerateApril to October

Appalachian Trail, Metacomet Trail, Mattabesett 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.

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