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Hiking Trails Over 20 km near Bridgeport

The directory currently contains 6 quality-checked routes matching this guide near Bridgeport. Their average mapped distance is 24.9 km and average recorded ascent is 510 m (1,673 ft); the longest route in the set is 31.5 km.

This subset represents 4% of the 153 quality-checked routes near Bridgeport. Its average distance is 24.9 km, compared with 3.2 km across the full local set. Average recorded ascent is 510 m (1,673 ft), versus 77 m (253 ft) for all quality-checked routes in the same area.

Every route in this set is at least 20 km long. Whether it is normally completed in one day or in stages is not inferred from distance alone. Within this set, 0 routes (0%) are rated easy, 6 (100%) are rated hard or expert, and 0 (0%) 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

20.9 km

Paugussett Trail

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

Lowest recorded ascent in this sample

201 m

The Branford 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

Round Hill Brook, Webb Mountain Park, Paugussett Trail, Monroe, CT.
Hard

Connecticut · United States

Distance
20.9 km
/ 13.0 mi
Elevation gain
508 m
Typical duration
5 hr 17 min
  • River
  • Forest
  • Waymarked route
Expert

Connecticut · United States

Distance
31.5 km
/ 19.6 mi
Elevation gain
848 m
Typical duration
8 hr 20 min
  • Forest
  • Waymarked route
Menunkatuck Blue-Blazed (CFPA) Trail. Vernal pond along the Menunkatuck Trail in the Timberlands near the Iron Stream. Timberlands is forested preserved open space owned by the Town of Guilford Connecticut and managed by the Town's Conserva
Hard

Connecticut · United States

Distance
25.8 km
/ 16.0 mi
Elevation gain
277 m
Typical duration
6 hr 7 min
  • Forest
  • Waymarked route
Hard

Connecticut · United States

Distance
21.5 km
/ 13.4 mi
Elevation gain
712 m
Typical duration
5 hr 45 min
  • Waymarked route
The blue girder bridge bearing the Tilcon logo carries the Branford Steam Railroad over U.S. Route 1 (Post Road) in Branford, Connecticut. This view is looking west.
Hard

Connecticut · United States

Distance
26.9 km
/ 16.7 mi
Elevation gain
201 m
Typical duration
6 hr 16 min
  • Waymarked route
Hard

Connecticut · United States

Distance
22.7 km
/ 14.1 mi
Elevation gain
515 m
Typical duration
5 hr 44 min

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
Paugussett TrailConnecticut20.9 km508 m5 hr 17 minHardApril to October
Quinnipiac TrailConnecticut31.5 km848 m8 hr 20 minExpertApril to October
Menunkatuck TrailConnecticut25.8 km277 m6 hr 7 minHardApril to October
Ives Trail GreenwayConnecticut21.5 km712 m5 hr 45 minHardApril to October
The Branford TrailConnecticut26.9 km201 m6 hr 16 minHardApril to October
Mission 22 TrailConnecticut22.7 km515 m5 hr 44 minHardApril to October

Paugussett Trail, Quinnipiac Trail, Menunkatuck 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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