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Loop Trails near Bridgeport

The directory currently contains 43 quality-checked routes matching this guide near Bridgeport. Their average mapped distance is 2.2 km and average recorded ascent is 54 m (177 ft); the longest route in the set is 10.2 km.

This subset represents 28% of the 153 quality-checked routes near Bridgeport. Its average distance is 2.2 km, compared with 3.2 km across the full local set.

Every route in this set is classified as a loop and returns to its starting area. A loop can still reuse part of the same path. Within this set, 27 routes (63%) are rated easy, 0 (0%) are rated hard or expert, and 43 (100%) 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

Trails

Easy

Munger Brook Trail

Connecticut · United States

Distance
1.3 km
/ 0.8 mi
Elevation gain
19 m
Typical duration
17 min
  • River
  • Waymarked route
Easy

Spencers Creek Trail

Connecticut · United States

Distance
0.7 km
/ 0.4 mi
Elevation gain
6 m
Typical duration
9 min
  • River
  • Waymarked route
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
Moderate

Delia Trail

Connecticut · United States

Distance
2.0 km
/ 1.2 mi
Elevation gain
75 m
Typical duration
32 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
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
Easy

Two Ridges Trail

Connecticut · United States

Distance
4.8 km
/ 3.0 mi
Elevation gain
170 m
Typical duration
1 hr 15 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
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
Easy

Eric L. Stone Trail

Connecticut · United States

Distance
3.8 km
/ 2.4 mi
Elevation gain
25 m
Typical duration
50 min
  • Waymarked route
Easy

Gneiss Trail

Connecticut · United States

Distance
2.1 km
/ 1.3 mi
Elevation gain
45 m
Typical duration
30 min
  • Waymarked route
Easy

Jamice's Loop

Connecticut · United States

Distance
0.7 km
/ 0.5 mi
Typical duration
9 min
  • Waymarked route
Little Free Library at St. John's Episcopal Church, North Guilford Connecticut
Easy

North Loop

Connecticut · United States

Distance
0.7 km
/ 0.5 mi
Elevation gain
12 m
Typical duration
10 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
Easy

Old Field

Connecticut · United States

Distance
1.1 km
/ 0.7 mi
Typical duration
13 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
Easy

Redwing Pond Trail

Connecticut · United States

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

Saul's Loop

Connecticut · United States

Distance
0.6 km
/ 0.3 mi
Typical duration
7 min
  • Waymarked route
Easy

Self-Guided Trail

Connecticut · United States

Distance
0.5 km
/ 0.3 mi
Typical duration
6 min
  • Waymarked route
Easy

Tulip Tree Trail

Connecticut · United States

Distance
0.6 km
/ 0.4 mi
Elevation gain
7 m
Typical duration
8 min
  • Waymarked route
Easy

Kelly Slide Trail

Connecticut · United States

Distance
0.5 km
/ 0.3 mi
Typical duration
6 min
  • Waymarked route
Easy

Meadow Walk

Connecticut · United States

Distance
0.6 km
/ 0.4 mi
Typical duration
8 min
  • Alpine meadow
View from Quinnipiac River Park in Fair Haven looking northeast toward the Fair Haven Heights neighborhood with the spire of Saint James Episcopal Church on East Grand Avenue visible.
Easy

River Walk

Connecticut · United States

Distance
0.5 km
/ 0.3 mi
Typical duration
7 min
  • River
Easy

Sargent River Trail

Connecticut · United States

Distance
1.9 km
/ 1.2 mi
Elevation gain
21 m
Typical duration
26 min
  • River
  • 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
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
Easy

Oak Hill Trail

Connecticut · United States

Distance
1.5 km
/ 0.9 mi
Elevation gain
21 m
Typical duration
20 min
  • Waymarked route
Easy

Tulip Tree Loop

Connecticut · United States

Distance
0.5 km
/ 0.3 mi
Typical duration
6 min
  • Waymarked route
Easy

White Trail

Connecticut · United States

Distance
0.9 km
/ 0.6 mi
Elevation gain
9 m
Typical duration
12 min
  • Waymarked route
Five Mile Point Light , located in New Haven, Connecticut , USA
Easy

Lighthouse Point Loop

Connecticut · United States

Distance
2.1 km
/ 1.3 mi
Elevation gain
8 m
Typical duration
27 min
Easy

Pink Trail (Off Leash Loop)

Connecticut · United States

Distance
2.8 km
/ 1.7 mi
Elevation gain
38 m
Typical duration
38 min
  • Waymarked route
Moderate

Blue Trail

Connecticut · United States

Distance
1.0 km
/ 0.6 mi
Elevation gain
25 m
Typical duration
14 min
  • Waymarked route
Moderate

Blue-Yellow Trail

Connecticut · United States

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

Nature Trail

Connecticut · United States

Distance
2.0 km
/ 1.3 mi
Elevation gain
44 m
Typical duration
29 min
  • Waymarked route
Easy

Riverbound Blue Trail

Connecticut · United States

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

Riverbound Orange Trail

Connecticut · United States

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

The Driftway

Connecticut · United States

Distance
2.1 km
/ 1.3 mi
Elevation gain
30 m
Typical duration
29 min
  • Waymarked route
Moderate

Yellow Loop

Connecticut · United States

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

Cabin Trail

Connecticut · United States

Distance
0.4 km
/ 0.2 mi
Typical duration
5 min
Easy

French's Hill Trail

Connecticut · United States

Distance
1.5 km
/ 0.9 mi
Elevation gain
49 m
Typical duration
23 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
Munger Brook TrailConnecticut1.3 km19 m17 minEasyApril to October
Spencers Creek TrailConnecticut0.7 km6 m9 minEasyApril to October
Zoar TrailConnecticut10.2 km341 m2 hr 38 minModerateApril to October
Blue TrailConnecticut1.5 km54 m24 minModerateApril to October
Delia TrailConnecticut2.0 km75 m32 minModerateApril to October
Lillinoah TrailConnecticut9.0 km310 m2 hr 20 minModerateApril to October
Mark Schaefer TrailConnecticut4.9 km105 m1 hr 10 minModerateApril to October
McCormack White TrailConnecticut2.9 km81 m43 minModerateApril to October
Steep Rock LoopConnecticut6.3 km160 m1 hr 33 minModerateApril to October
Two Ridges TrailConnecticut4.8 km170 m1 hr 15 minEasyApril to October

Spencers Creek Trail, Munger Brook Trail, Gneiss 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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