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Moderate Hiking Trails near Bridgeport

The directory currently contains 63 quality-checked routes matching this guide near Bridgeport. Their average mapped distance is 2.9 km and average recorded ascent is 96 m (315 ft); the longest route in the set is 12.7 km.

This subset represents 41% of the 153 quality-checked routes near Bridgeport.

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 16 (25%) 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

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

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
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
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
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

Baldy Ridge Trail

Connecticut · United States

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

Hardwood Trail

Connecticut · United States

Distance
1.9 km
/ 1.2 mi
Elevation gain
30 m
Typical duration
27 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
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
Moderate

Mark Schaefer Trail

Connecticut · United States

Distance
4.9 km
/ 3.0 mi
Elevation gain
105 m
Typical duration
1 hr 10 min
  • Waymarked route
Moderate

McCormack White Trail

Connecticut · United States

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

Nature Trail

Connecticut · United States

Distance
1.7 km
/ 1.1 mi
Elevation gain
72 m
Typical duration
28 min
  • Waymarked route
Moderate

Old Mattabessett Trail

Connecticut · United States

Distance
0.4 km
/ 0.3 mi
Elevation gain
69 m
Typical duration
12 min
  • Waymarked route
Moderate

Old Oak Nature Trail Loop

Connecticut · United States

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

Orange Trail

Connecticut · United States

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

Perimeter Trail

Connecticut · United States

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

Pinney Loop

Connecticut · United States

Distance
3.4 km
/ 2.1 mi
Elevation gain
98 m
Typical duration
51 min
  • Waymarked route
Moderate

Purple Trail

Connecticut · United States

Distance
1.7 km
/ 1.1 mi
Elevation gain
19 m
Typical duration
23 min
  • Waymarked route
Moderate

Red Trail

Connecticut · United States

Distance
2.2 km
/ 1.4 mi
Elevation gain
91 m
Typical duration
36 min
  • Waymarked route
Moderate

Ski Trail

Connecticut · United States

Distance
4.5 km
/ 2.8 mi
Elevation gain
140 m
Typical duration
1 hr 9 min
  • Waymarked route
The Steep Rock Association gate across the former right of way of the Shepaug, Litchfield and Northern Railroad in Washington, just south of Washington Depot. The Shepaug River is visible through the trees to the left of the trailhead signb
Moderate

Steep Rock Loop

Connecticut · United States

Distance
6.3 km
/ 3.9 mi
Elevation gain
160 m
Typical duration
1 hr 33 min
  • Waymarked route
Moderate

Westville Feeder

Connecticut · United States

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

Yellow Trail

Connecticut · United States

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

Burn Trail

Connecticut · United States

Distance
0.8 km
/ 0.5 mi
Elevation gain
51 m
Typical duration
15 min
  • Waymarked route
The south portal of the Shepaug railroad tunnel through the "Clamshell" in the Steep Rock Preserve in Washington, Connecticut.
Moderate

Clamshell Loop

Connecticut · United States

Distance
3.6 km
/ 2.3 mi
Elevation gain
92 m
Typical duration
54 min
  • Waymarked route
Moderate

Oak Trail

Connecticut · United States

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

Old Milan Trail

Connecticut · United States

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

Red Trail

Connecticut · United States

Distance
1.9 km
/ 1.2 mi
Elevation gain
57 m
Typical duration
29 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

Aspetuck Valley Trail

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

Birchbank Trail

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

Oxford Loop Trail

Connecticut · United States

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

Blue Trail

Connecticut · United States

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

Green-Yellow Trail

Connecticut · United States

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

McCormack Blue Trail

Connecticut · United States

Distance
3.1 km
/ 1.9 mi
Elevation gain
81 m
Typical duration
46 min
  • Waymarked route
View from scenic overloop of the Housatonic River's Lake Zoar (along the Miller Trail in Kettletown State Park).
Moderate

Miller Trail

Connecticut · United States

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

North Slope Connector

Connecticut · United States

Distance
0.7 km
/ 0.4 mi
Typical duration
9 min
  • Waymarked route
Moderate

Orange Trail

Connecticut · United States

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

Paine Barn Trail

Connecticut · United States

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

White Trail

Connecticut · United States

Distance
0.6 km
/ 0.4 mi
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
North Summit TrailConnecticut1.3 km10 m17 minModerateApril to October
Beacon Falls Yellow TrailConnecticut2.8 km153 m49 minModerateApril to October
Hancock Brook TrailConnecticut4.2 km212 m1 hr 11 minModerateApril to October
Ives Trail Greenway AlternativeConnecticut2.5 km159 m45 minModerateApril to October
Regicides TrailConnecticut11.0 km243 m2 hr 40 minModerateApril to October
Baldy Ridge TrailConnecticut0.6 km31 m10 minModerateApril to October
Naugatuck Trail (Woodbridge)Connecticut12.7 km218 m2 hr 58 minModerateApril to October
Pomperaug TrailConnecticut6.6 km325 m1 hr 52 minModerateApril to October
Roaring Brook Falls TrailConnecticut0.9 km115 m21 minModerateApril to October
Zoar TrailConnecticut10.2 km341 m2 hr 38 minModerateApril to October

North Summit Trail, Beacon Falls Yellow Trail, Hancock Brook 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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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.

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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.

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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.

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