Skip to content

Moderate Hiking Trails near Poughkeepsie

The directory currently contains 11 quality-checked routes matching this guide near Poughkeepsie. Their average mapped distance is 2.4 km and average recorded ascent is 124 m (407 ft); the longest route in the set is 10.3 km.

This subset represents 69% of the 16 quality-checked routes near Poughkeepsie. Its average distance is 2.4 km, compared with 3.3 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 2 (18%) 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

0.9 km

Caleb's Peak Trail

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

Lowest recorded ascent in this sample

0 m

Cerulean Warbler Loop

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

Return logistics

1 recorded loop

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

Moderate

Caleb's Peak Trail

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

Cobble Mountain Trail

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

Macedonia Ridge Trail

Connecticut · United States

Distance
10.3 km
/ 6.4 mi
Elevation gain
513 m
Typical duration
2 hr 55 min
  • Mountain
  • Waymarked route
Moderate

Mountain Trail

Connecticut · United States

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

Cerulean Warbler Loop

Connecticut · United States

Distance
2.3 km
/ 1.4 mi
Typical duration
28 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. Gaylordsville Cemetary in Gaylordsville, Connecticut. Housatonic Range Trail north
Moderate

Housatonic Range Trail

Connecticut · United States

Distance
4.4 km
/ 2.8 mi
Elevation gain
262 m
Typical duration
1 hr 19 min
  • Waymarked route
Moderate

Queen of Diamonds Loop

Connecticut · United States

Distance
2.5 km
/ 1.6 mi
Elevation gain
113 m
Typical duration
42 min
  • Waymarked route
Moderate

Red Gate Trail

Connecticut · United States

Distance
1.2 km
/ 0.7 mi
Elevation gain
52 m
Typical duration
20 min
  • Waymarked route
Moderate

Saturday Afternoon Trail

Connecticut · United States

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

Escarpment Trail

Connecticut · United States

Distance
0.5 km
/ 0.3 mi
Elevation gain
22 m
Typical duration
8 min
  • Waymarked route
Moderate

Silo Trail

Connecticut · United States

Distance
0.5 km
/ 0.3 mi
Elevation gain
25 m
Typical duration
8 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
Caleb's Peak TrailConnecticut0.9 km21 m13 minModerateApril to October
Cobble Mountain TrailConnecticut1.4 km194 m35 minModerateApril to October
Macedonia Ridge TrailConnecticut10.3 km513 m2 hr 55 minModerateApril to October
Mountain TrailConnecticut1.0 km115 m22 minModerateApril to October
Cerulean Warbler LoopConnecticut2.3 km0 m28 minModerateApril to October
Housatonic Range TrailConnecticut4.4 km262 m1 hr 19 minModerateApril to October
Queen of Diamonds LoopConnecticut2.5 km113 m42 minModerateApril to October
Red Gate TrailConnecticut1.2 km52 m20 minModerateApril to October
Saturday Afternoon TrailConnecticut1.6 km46 m25 minModerateApril to October
Escarpment TrailConnecticut0.5 km22 m8 minModerateApril to October

Caleb's Peak Trail, Cobble Mountain Trail, Macedonia Ridge 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 →

Related guides

Other shortlists covering the same area or the same kind of terrain.

People also search for