82 official trails lie within 25 miles of Bridgeport — 298 miles in total, 55 rated easy and 17 hard or expert. Every distance and elevation figure below is computed from the agency centerline and a 10 m elevation model, not crowd-sourced.
The biggest climb nearby gains 653 ft; the median trail gains 212 ft.
| Trail | Miles | Climb | Difficulty | From town |
|---|---|---|---|---|
| Sleeping Giant Park Trail | 25.1 | 616 ft | Expert | 22 mi |
| Huntington Park Trail | 22.8 | 310 ft | Expert | 13 mi |
| West Rock Park Trail | 14.3 | 564 ft | Expert | 16 mi |
| Naugatuck Forest Trail | 7.7 | 389 ft | Expert | 13 mi |
| Paugussett Forest Trail | 7.7 | 489 ft | Expert | 14 mi |
| Pierrepont Park Trail | 6.4 | 381 ft | Hard | 19 mi |
| Quinnipiac Trail | 5.0 | 653 ft | Hard | 22 mi |
| Zoar Trail | 6.5 | 546 ft | Hard | 15 mi |
| Lillinonah Trail | 6.3 | 331 ft | Hard | 20 mi |
| Regicides Trail | 7.0 | 347 ft | Hard | 20 mi |
| Osbornedale Park Trail | 5.1 | 317 ft | Hard | 12 mi |
| Larkin Bridle Trail | 10.7 | 336 ft | Hard | 20 mi |
| West Rock Trail | 6.5 | 469 ft | Hard | 16 mi |
| Grta | 6.8 | 220 ft | Hard | 22 mi |
| Naugatuck Trail | 4.8 | 459 ft | Hard | 21 mi |
| Aspetuck Valley Trail | 5.8 | 360 ft | Moderate | 10 mi |
| Southford Falls Park Trail | 2.6 | 270 ft | Moderate | 18 mi |
| Farmington Canal Trail | 10.6 | 107 ft | Moderate | 20 mi |
| Pomperaug Trail | 2.0 | 435 ft | Moderate | 15 mi |
| Pomparaug Trail | 2.3 | 351 ft | Moderate | 15 mi |
| Tower Trail | 1.5 | 606 ft | Easy | 22 mi |
| Pisgah Brook | 3.6 | 141 ft | Moderate | 22 mi |
| Ives Trail | 2.5 | 212 ft | Easy | 18 mi |
| Short Beach | 5.0 | 114 ft | Easy | 18 mi |
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