Massachusetts trails · Loop hikes
Loops computed from the connected trail network — each starts and ends at the same trailhead. Explore any of them on the interactive map (Loops layer).
| Route | Distance | Gain | Trailhead |
|---|---|---|---|
| New Lenox Road + NEW LENOX ROAD + Ashley Lake Road | 15.4 mi | 2,367 ft | Unnamed trail access |
| Ashley Lake Road + ASHLEY LAKE ROAD + APPALACHIAN TRAIL | 14.5 mi | 1,940 ft | Ashley Lake Road access |
| Utility Corridor + Unnamed trail + WATSON ROAD EXTENSION | 14.5 mi | 1,957 ft | UTILITY CORRIDOR access |
| UTILITY CORRIDOR + Utility Corridor + Washington Mountain Marsh Trail | 14.5 mi | 1,941 ft | UTILITY CORRIDOR access |
| New Lenox Road + NEW LENOX ROAD + Ashley Lake Road | 15.1 mi | 2,086 ft | Unnamed trail access |
| Money Brook Trail + Unnamed trail + HOPPER ROAD | 12.2 mi | 4,292 ft | Unnamed trail access |
| WHITNEY PLACE ROAD + Unnamed trail + New Lenox Road | 15.8 mi | 2,038 ft | Unnamed trail access |
| Midstate Trail + Unnamed trail + MIDSTATE TRAIL | 15.8 mi | 1,183 ft | MIDSTATE TRAIL access |
| Midstate Trail + Unnamed trail + CORRIDOR 71 | 15.9 mi | 1,189 ft | Midstate Trail access |
| MIDSTATE TRAIL + Midstate Trail + Unnamed trail | 15.9 mi | 1,219 ft | Unnamed trail access |
| Midstate Trail + MIDSTATE TRAIL + Unnamed trail | 15.9 mi | 1,168 ft | Midstate Trail access |
| HOPPER ROAD + Haley Farm Trail + Haley Farm Trail (Steep Route) | 13.3 mi | 4,723 ft | Haley Farm Trailhead |
| Unnamed trail + Money Brook Trail + MONEY BROOK TRAIL | 13.7 mi | 5,141 ft | Haley Farm Trailhead |
| Unnamed trail + APPALACHIAN TRAIL/LONG TRAIL + Appalachian National Scenic Trail | 13.0 mi | 4,576 ft | Old Summit Road access |
| Money Brook Trail + Unnamed trail + HOPPER ROAD | 13.7 mi | 5,135 ft | Unnamed trail access |
| CORRELLUS BIKE PATH + Correllus Bike Path + Unnamed trail | 5.2 mi | 139 ft | FIRE ROAD 54 access |
| Unnamed trail + Hopper Trail + Cut off to Money Brook Trail | 12.9 mi | 4,408 ft | Haley Farm Trailhead |
| White Pond Trail + Taylor Way + WINTERBERRY WAY | 5.2 mi | 201 ft | Trail C access |
| Puffer Pond Trail + PUFFER POND TRAIL + WINTERBERRY WAY | 5.4 mi | 220 ft | Puffer Pond Trail access |
| Winterberry Way + Puffer Pond Trail + WINTERBERRY WAY | 5.4 mi | 219 ft | Winterberry Way access |
| Unnamed trail + Gould Trail + OLD ADAMS ROAD | 5.8 mi | 2,130 ft | Cottontail Trail access |
| FENTON ROAD + Unnamed trail + Ball Hill Trail | 6.2 mi | 864 ft | Unnamed trail access |
| Appalachian National Scenic Trail + Gould Trail + Unnamed trail | 5.4 mi | 2,157 ft | Thunderbolt Trail access |
| Taconic Skyline Trail + William Berry trail + Taconic Crest Trail | 9.8 mi | 2,513 ft | Lulu Brook Trail access |
| North Pond Loop + Lost Pond Trail + OLD FLORIDA ROAD | 8.9 mi | 1,271 ft | Unnamed trail access |
| CEDAR SWAMP ROAD + Unnamed trail + EDMUND HOUSE TRAIL | 3.9 mi | 166 ft | Unnamed trail access |
| EDMOND HOUSE TRAIL + Edmond House Trail + EDMUND HOUSE TRAIL | 3.9 mi | 167 ft | Unnamed trail access |
| Unnamed trail + Gould Trail + Appalachian National Scenic Trail | 5.2 mi | 2,203 ft | Cottontail Trail access |
| SKYLINE, RESERVOIR AND MOUNTAIN BIKE + Mountain Bike + SKYLINE AND RESERVOIR | 4.9 mi | 765 ft | Skyline, Reservoir and Mountain Bike access |
| FIRE ROAD 50 + LITTLE POND ROAD + Unnamed trail | 5.5 mi | 192 ft | Unnamed trail access |
| Skyline, Reservoir and Mountain Bike + Reservoir and Mountain Bike + RESERVOIR AND MOUNTAIN BIKE | 5.0 mi | 767 ft | Unnamed trail access |
| Skyline, Reservoir and Mountain Bike + Unnamed trail + MOUNTAIN BIKE AND NANEPASHEMET RD | 5.2 mi | 861 ft | Skyline Trail access |
| Old Wildcat Trail + Wildcat Trail + Old Taconic Skyline Trail | 7.3 mi | 1,993 ft | Unnamed trail access |
| Winterberry Way + HARRY'S WAY + Trail C | 3.5 mi | 132 ft | Hill Trail access |
| Unnamed trail | 7.1 mi | 882 ft | Unnamed trail access |
| Trail C + OTTER ALLEY + Otter Alley | 4.4 mi | 200 ft | Towhee Trail access |
| Balance Rock Trail + BALANCE ROCK TRAIL + Potter Mountain Trail | 4.7 mi | 1,106 ft | Balance Rock Trail access |
| EDMOND HOUSE TRAIL + Edmond House Trail + Unnamed trail | 5.4 mi | 258 ft | Unnamed trail access |
| Dry Brook Trail + DRY BROOK TRAIL + Lithia Springs Trail | 6.1 mi | 1,678 ft | Dry Brook Trail access |
| CEDAR SWAMP ROAD + Unnamed trail + EDMUND HOUSE TRAIL | 4.3 mi | 183 ft | Unnamed trail access |
| Finerty Trail + FINERTY TRAIL + CORDONIER TRAIL | 6.1 mi | 1,086 ft | Finerty Trail access |
| Sucker Brook Trail + Adams Sno-Drifter Trail + Florida Trail | 8.3 mi | 1,289 ft | Sucker Brook Trail access |
| Sucker Brook Trail + Mahican Mohawk Trail + BOG POND TRAIL | 8.3 mi | 1,299 ft | Sucker Brook Trail access |
| Jourdan Road + Unnamed trail + Horse Hill Brook Road | 3.9 mi | 675 ft | Jourdan Road access |
| EDMOND HOUSE TRAIL + Edmond House Trail + Unnamed trail | 5.3 mi | 250 ft | Unnamed trail access |
| Towhee Trail + PETAPAWAG TRAIL + Trail A | 3.4 mi | 107 ft | Towhee Trail access |
| Skyline, Reservoir and Mountain Bike + SKYLINE, RESERVOIR AND MOUNTAIN BIKE + Reservoir Trail | 4.8 mi | 681 ft | Skyline, Reservoir and Mountain Bike access |
| New Lenox Road + WHITNEY PLACE ROAD + Unnamed trail | 4.4 mi | 764 ft | New Lenox Road access |
| Skyline, Reservoir and Mountain Bike + Unnamed trail + MOUNTAIN BIKE AND NANEPASHEMET RD | 4.9 mi | 706 ft | Skyline Trail access |
| Unnamed trail | 8.1 mi | 379 ft | Unnamed trail access |