151 official trails lie within 25 miles of Waterbury — 792 miles in total, 95 rated easy and 31 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 894 ft; the median trail gains 174 ft.
| Trail | Miles | Climb | Difficulty | From town |
|---|---|---|---|---|
| Sleeping Giant Park Trail | 25.1 | 616 ft | Expert | 12 mi |
| Nassahegon Forest Trail | 14.2 | 350 ft | Expert | 15 mi |
| New England National Scenic Trail | 122.9 | 827 ft | Expert | 23 mi |
| Huntington Park Trail | 22.8 | 310 ft | Expert | 23 mi |
| West Rock Park Trail | 14.3 | 564 ft | Expert | 15 mi |
| cockaponset forest trail | 9.9 | 219 ft | Expert | 22 mi |
| Naugatuck Forest Trail | 7.7 | 389 ft | Expert | 15 mi |
| Millers Pond Park Trail | 11.2 | 313 ft | Expert | 22 mi |
| Paugussett Forest Trail | 7.7 | 489 ft | Expert | 14 mi |
| Pootatuck Forest Trail | 4.9 | 738 ft | Hard | 24 mi |
| Nepaug Forest Trail | 7.1 | 249 ft | Hard | 19 mi |
| Quinnipiac Trail | 5.0 | 653 ft | Hard | 12 mi |
| Zoar Trail | 6.5 | 546 ft | Hard | 13 mi |
| Lillinonah Trail | 6.3 | 331 ft | Hard | 16 mi |
| Mattatuck Trail | 4.2 | 436 ft | Hard | 7 mi |
| Regicides Trail | 7.0 | 347 ft | Hard | 12 mi |
| Mohawk Forest Trail | 5.8 | 581 ft | Hard | 21 mi |
| Mohawk Trail | 5.1 | 588 ft | Hard | 24 mi |
| River Highland Park Trail | 7.2 | 144 ft | Hard | 21 mi |
| Osbornedale Park Trail | 5.1 | 317 ft | Hard | 15 mi |
| Larkin Bridle Trail | 10.7 | 336 ft | Hard | 11 mi |
| West Rock Trail | 6.5 | 469 ft | Hard | 15 mi |
| millers pond park trail | 7.1 | 147 ft | Hard | 22 mi |
| Naugatuck Trail | 4.8 | 459 ft | Hard | 7 mi |
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