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Moderate Hiking Trails near Stamford

The directory currently contains 38 quality-checked routes matching this guide near Stamford. Their average mapped distance is 2.6 km and average recorded ascent is 85 m (279 ft); the longest route in the set is 11.1 km.

This subset represents 43% of the 89 quality-checked routes near Stamford.

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 11 (29%) 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

0.6 km

Baldy Ridge Trail

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

Lowest recorded ascent in this sample

31 m

Baldy Ridge Trail

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

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
6.6 km
/ 4.1 mi
Elevation gain
325 m
Typical duration
1 hr 52 min
  • Forest
  • Waymarked route
Moderate

Connecticut · United States

Distance
10.2 km
/ 6.3 mi
Elevation gain
341 m
Typical duration
2 hr 38 min
  • Waymarked route
View from Kettletown State Park's Crest Trail of the Housatonic River's Lake Zoar looking south towards Oxford.
Moderate

Connecticut · United States

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

Connecticut · United States

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

Connecticut · United States

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

Connecticut · United States

Distance
1.9 km
/ 1.2 mi
Elevation gain
30 m
Typical duration
27 min
  • Waymarked route
Moderate

Connecticut · United States

Distance
1.3 km
/ 0.8 mi
Elevation gain
31 m
Typical duration
19 min
  • Waymarked route
Moderate

Connecticut · United States

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

Connecticut · United States

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

Connecticut · United States

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

Connecticut · United States

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

Connecticut · United States

Distance
1.3 km
/ 0.8 mi
Elevation gain
34 m
Typical duration
19 min
  • Waymarked route
Aspetuck Valley Trail. Blue-Blazed CFPA foot path in Connecticut Centennial Watershed State Forest which connects to Huntington State Park at the northern terminus and which follows the Aspetuck River from Newtown, CT through Redding and Ea
Moderate

Connecticut · United States

Distance
11.1 km
/ 6.9 mi
Elevation gain
166 m
Typical duration
2 hr 34 min
  • Waymarked route
Photo of northbound Birchbank Road in an unnamed neighborhood along the Housatonic River in Shelton , Connecticut . Photo taken looking north.
Moderate

Connecticut · United States

Distance
2.5 km
/ 1.6 mi
Elevation gain
87 m
Typical duration
39 min
  • Waymarked route
View from Kettletown State Park's Crest Trail of the Housatonic River's Lake Zoar looking south towards Oxford.
Moderate

Connecticut · United States

Distance
0.6 km
/ 0.4 mi
Elevation gain
20 m
Typical duration
9 min
  • Forest
  • Waymarked route
Moderate

Connecticut · United States

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

Connecticut · United States

Distance
3.1 km
/ 1.9 mi
Elevation gain
81 m
Typical duration
46 min
  • Waymarked route
Moderate

Connecticut · United States

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

Connecticut · United States

Distance
0.6 km
/ 0.4 mi
Typical duration
8 min
  • Waymarked route
Moderate

Connecticut · United States

Distance
0.5 km
/ 0.3 mi
Elevation gain
46 m
Typical duration
10 min
  • Coastal
  • Waymarked route
Moderate

Connecticut · United States

Distance
3.9 km
/ 2.4 mi
Elevation gain
180 m
Typical duration
1 hr 5 min
  • Waymarked route
Moderate

Connecticut · United States

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

Connecticut · United States

Distance
7.1 km
/ 4.4 mi
Elevation gain
80 m
Typical duration
1 hr 36 min
  • Waymarked route
Moderate

Connecticut · United States

Distance
1.5 km
/ 0.9 mi
Elevation gain
35 m
Typical duration
22 min
Moderate

Connecticut · United States

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

Connecticut · United States

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

Connecticut · United States

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

Connecticut · United States

Distance
1.3 km
/ 0.8 mi
Elevation gain
23 m
Typical duration
19 min
  • Waymarked route
Moderate

Connecticut · United States

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

Connecticut · United States

Distance
0.7 km
/ 0.4 mi
Elevation gain
21 m
Typical duration
10 min
  • Waymarked route
Moderate

Connecticut · United States

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

Connecticut · United States

Distance
3.5 km
/ 2.1 mi
Elevation gain
73 m
Typical duration
50 min
  • Waymarked route
Moderate

Connecticut · United States

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

Connecticut · United States

Distance
2.4 km
/ 1.5 mi
Elevation gain
103 m
Typical duration
39 min
  • Waymarked route
Moderate

Connecticut · United States

Distance
0.9 km
/ 0.6 mi
Elevation gain
33 m
Typical duration
14 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
Ives Trail Greenway AlternativeConnecticut2.5 km159 m45 minModerateApril to October
Baldy Ridge TrailConnecticut0.6 km31 m10 minModerateApril to October
Pomperaug TrailConnecticut6.6 km325 m1 hr 52 minModerateApril to October
Zoar TrailConnecticut10.2 km341 m2 hr 38 minModerateApril to October
Crest TrailConnecticut3.2 km117 m50 minModerateApril to October
Dan Beard TrailConnecticut1.5 km43 m23 minModerateApril to October
Delia TrailConnecticut2.0 km75 m32 minModerateApril to October
Hardwood TrailConnecticut1.9 km30 m27 minModerateApril to October
Knapp WayConnecticut1.3 km31 m19 minModerateApril to October
Lillinoah TrailConnecticut9.0 km310 m2 hr 20 minModerateApril to October

Ives Trail Greenway Alternative, Baldy Ridge Trail, Pomperaug 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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