Massachusetts, United States trails

Distance: 3.6 mi • Elevation gain: 85 ft • Maximum elevation: 23 ft

Distance: 9.0 mi • Elevation gain: 505 ft • Maximum elevation: 433 ft

The Devil's Pulpit Overlook Loop on Monument Mountain offers a moderately challenging hike rich in both natural beauty and historical significance. Combining the Hickey Trail, Peeskawso Peak Trail, and Mohican Monument Trail, the loop winds through dense forest, revealing ancient quartzite rock formations and…

Distance: 2.5 mi • Elevation gain: 673 ft • Maximum elevation: 1,522 ft

Walking Boston's Freedom Trail offers a seamless journey through America’s Revolutionary history, with a lively path marked by historic buildings and memorials, from the lush Boston Common to the monumental Bunker Hill. Each stop, such as the Old South Meeting House and Faneuil Hall, is packed with stories…

Distance: 2.4 mi • Elevation gain: 207 ft • Maximum elevation: 125 ft

The Bellows Pipe Trail on Mount Greylock provides a scenic ascent through dense forests, culminating in stunning summit views. Hikers pass through lush hardwood groves, a segment of the Appalachian Trail, and reach the iconic Veterans War Memorial Tower, which offers expansive vistas of the surrounding…

Distance: 5.7 mi • Elevation gain: 2,241 ft • Maximum elevation: 3,484 ft

The Mount Watatic Loop offers a beautiful New England hiking experience, combining forested paths with rewarding summit views. Following the Wapack, Mid State, and State Line trails, the route brings you to the peak of Mount Watatic, where on clear days, you can enjoy wide vistas stretching from Mount…

Distance: 2.8 mi • Elevation gain: 666 ft • Maximum elevation: 1,788 ft

The Mount Norwottuck Loop is a moderate, scenic hike through Mount Holyoke Range State Park that leads to panoramic views of the Pioneer Valley and diverse wooded landscapes. Following the NET/M&M Trail and connecting with the Robert Frost Trail, hikers can explore the historical Horse Caves, which were…

Distance: 3.6 mi • Elevation gain: 650 ft • Maximum elevation: 1,043 ft

The Skyline and Reservoir Loop Trail offers a moderately challenging experience with rugged terrain, rewarding hikers with sweeping views of the Boston skyline. As the trail winds through forested sections and around scenic reservoirs, it also climbs to rocky summits, providing natural vantage points. This…

Distance: 8.0 mi • Elevation gain: 548 ft • Maximum elevation: 259 ft

This loop offers a diverse hiking experience with a blend of rocky ascents, shaded woods, and stunning vistas. Hikers can enjoy panoramic views of the Boston skyline from various points along the route, particularly from Nahanton Hill, while also passing serene spots like Saint Moritz Pond. This loop presents…

Distance: 5.4 mi • Elevation gain: 545 ft • Maximum elevation: 453 ft

The Mount Wachusett Loop offers a captivating experience amidst varied terrain. Hikers can enjoy serene forested paths leading to the summit, where panoramic views showcase the distant Boston skyline, particularly stunning during clear weather. The trail combines moderate inclines with sections that reveal…

Distance: 4.0 mi • Elevation gain: 1,010 ft • Maximum elevation: 1,991 ft

The Rock Circuit Loop Trail is a captivating route that showcases a variety of unique rock formations and stunning vistas. Hikers will experience the impressive sights from Boojum Rock and Melrose Rock, where expansive views of Boston and the surrounding area can be enjoyed. The trail combines challenging…

Distance: 4.6 mi • Elevation gain: 335 ft • Maximum elevation: 272 ft

The Eliot Tower and Great Blue Hill Loop offers hikers a rewarding blend of natural beauty and historical significance. As you traverse the rocky terrain, you’ll encounter stunning panoramic views of the Boston skyline and the surrounding landscape from the summit of Great Blue Hill, making it an ideal spot…

Distance: 3.3 mi • Elevation gain: 741 ft • Maximum elevation: 614 ft

Distance: 22.8 mi • Elevation gain: 1,129 ft • Maximum elevation: 367 ft

Distance: 73.1 mi • Elevation gain: 6,909 ft • Maximum elevation: 1,588 ft

Distance: 14.1 mi • Elevation gain: 958 ft • Maximum elevation: 449 ft

Mount Toby State Forest Trail Running

Distance: 6.2 mi • Elevation gain: 810 ft • Maximum elevation: 899 ft

Sunderland Trail Running

Distance: 10.6 mi • Elevation gain: 1,427 ft • Maximum elevation: 1,066 ft

Distance: 106.4 mi • Elevation gain: 5,623 ft • Maximum elevation: 600 ft

Mount Toby State Forest Trail Running

Distance: 9.0 mi • Elevation gain: 1,237 ft • Maximum elevation: 896 ft

Loop hike in the Borderland State Park via Northwest Trail, Split Rock Trail, Granite Hills Trail, Granite Hills Lower Loop, Tisdale Road, Upper Leach Pond, Puds Pond, Pond Walk, Leach Pond, Pond Edge Trail, West Side Trail and The French Trail. #Hiking #Loop #Park #Nature #Lake #Forest

Distance: 5.9 mi • Elevation gain: 266 ft • Maximum elevation: 318 ft

Afternoon Ride

Distance: 12.2 mi • Elevation gain: 633 ft • Maximum elevation: 213 ft

Distance: 30.1 mi • Elevation gain: 1,529 ft • Maximum elevation: 400 ft

Medford/Dover trails

Distance: 26.9 mi • Elevation gain: 1,440 ft • Maximum elevation: 400 ft

Hike to Mount Greylock via Glen Meadow Loop, Bellows Pipe Trail, Thunderbolt Ski Trail and Appalachian Trail in the Mount Greylock State Reservation and the Greylock Glen. #Hiking #Mountain #Nature #Forest #Appalachian

Distance: 5.6 mi • Elevation gain: 2,392 ft • Maximum elevation: 3,484 ft

Loop hike through Westville Conservation Area. #Hiking #Loop #Nature #Forest #River

Distance: 3.8 mi • Elevation gain: 75 ft • Maximum elevation: 52 ft

Hike through Hockomock Swamp. #Hiking #Swamp #Nature #Forest #Lake

Distance: 2.3 mi • Elevation gain: 46 ft • Maximum elevation: 82 ft

Loop hike from Newton Highlands via Winchester Street, Nahanton Park, Charles River, Kendrick Street, Healthy Heart Trail, Kendrick Pond, Blue Heron Trail, Powells Island, Fourth Avenue, Upper Charles River Reservation and Needham Street. #Hiking #Loop #Nature #Forest #River #City

Distance: 10.3 mi • Elevation gain: 354 ft • Maximum elevation: 161 ft

Distance: 1.4 mi • Elevation gain: 26 ft • Maximum elevation: 39 ft

Distance: 17.7 mi • Elevation gain: 1,053 ft • Maximum elevation: 400 ft

Distance: 1.9 mi • Elevation gain: 62 ft • Maximum elevation: 233 ft

Distance: 28.3 mi • Elevation gain: 1,365 ft • Maximum elevation: 354 ft

Distance: 1.5 mi • Elevation gain: 210 ft • Maximum elevation: 266 ft

Distance: 2.7 mi • Elevation gain: 52 ft • Maximum elevation: 36 ft

Distance: 67.0 mi • Elevation gain: 3,251 ft • Maximum elevation: 407 ft

Weston Trails

Distance: 8.6 mi • Elevation gain: 390 ft • Maximum elevation: 331 ft

More exploring

Distance: 55.7 mi • Elevation gain: 2,575 ft • Maximum elevation: 344 ft

Weston Trails, lots of areas including Dear Path Conservation Area

Distance: 30.4 mi • Elevation gain: 1,608 ft • Maximum elevation: 354 ft

Distance: 126.0 mi • Elevation gain: 5,942 ft • Maximum elevation: 548 ft

Mountain Bike F. Gilbert Hills State Forest

Distance: 19.1 mi • Elevation gain: 879 ft • Maximum elevation: 338 ft

Newton Trails

Distance: 16.3 mi • Elevation gain: 810 ft • Maximum elevation: 289 ft

Distance: 22.9 mi • Elevation gain: 945 ft • Maximum elevation: 174 ft

Distance: 69.2 mi • Elevation gain: 3,392 ft • Maximum elevation: 358 ft

Exploring Medfield

Distance: 47.0 mi • Elevation gain: 2,510 ft • Maximum elevation: 344 ft

Distance: 10.0 mi • Elevation gain: 476 ft • Maximum elevation: 302 ft

Distance: 1.4 mi • Elevation gain: 108 ft • Maximum elevation: 433 ft

Distance: 10.0 mi • Elevation gain: 449 ft • Maximum elevation: 118 ft

More investigations

Distance: 46.0 mi • Elevation gain: 2,188 ft • Maximum elevation: 344 ft

River Ride, both sides

Distance: 16.4 mi • Elevation gain: 545 ft • Maximum elevation: 46 ft

Distance: 49.0 mi • Elevation gain: 2,536 ft • Maximum elevation: 400 ft

Wandering

Distance: 21.6 mi • Elevation gain: 1,060 ft • Maximum elevation: 220 ft

Distance: 126.6 mi • Elevation gain: 6,365 ft • Maximum elevation: 636 ft

Lancaster Trails, Cook Conservation Area, Nashua River, Chapman-Goodale Conservation Land, Lancaster State Forest

Distance: 5.7 mi • Elevation gain: 299 ft • Maximum elevation: 377 ft

Cape Cod National Seashore

Distance: 60.7 mi • Elevation gain: 2,608 ft • Maximum elevation: 118 ft

Afternoon Ride

Distance: 35.2 mi • Elevation gain: 830 ft • Maximum elevation: 62 ft

Distance: 12.5 mi • Elevation gain: 295 ft • Maximum elevation: 46 ft

Evening Ride

Distance: 22.0 mi • Elevation gain: 817 ft • Maximum elevation: 108 ft

Rocky Woods

Distance: 41.3 mi • Elevation gain: 1,886 ft • Maximum elevation: 348 ft

Distance: 1.9 mi • Elevation gain: 135 ft • Maximum elevation: 207 ft

Distance: 8.5 mi • Elevation gain: 719 ft • Maximum elevation: 440 ft

Some Wellesley trails

Distance: 41.4 mi • Elevation gain: 2,005 ft • Maximum elevation: 348 ft

Distance: 46.0 mi • Elevation gain: 2,244 ft • Maximum elevation: 308 ft

Sudbury sections of Bruce Freeman and new MCRT section from Union St

Distance: 52.8 mi • Elevation gain: 2,280 ft • Maximum elevation: 295 ft

Alewife -> Providence

Distance: 63.2 mi • Elevation gain: 3,153 ft • Maximum elevation: 351 ft

Assabat River Trail Hudson -> Maynard

Distance: 64.4 mi • Elevation gain: 2,415 ft • Maximum elevation: 459 ft

Northfield Mountain Yellow

Distance: 4.9 mi • Elevation gain: 666 ft • Maximum elevation: 955 ft

Distance: 9.1 mi • Elevation gain: 348 ft • Maximum elevation: 272 ft

Bike Loop Bellevue

Distance: 7.0 mi • Elevation gain: 413 ft • Maximum elevation: 289 ft

Quarry Route in Ashland

Distance: 1.8 mi • Elevation gain: 135 ft • Maximum elevation: 344 ft