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Devil's Pulpit Overlook Loop via Hickey Trail, Peeskawso Peak Trail and Mohican Monument Trail in Monument Mountain Reservation

United States > Massachusetts > Berkshire County > Great Barrington

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: 205 m • Maximum elevation: 464 m

Boston's Freedom Trail

United States > Massachusetts > Suffolk County > Boston

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: 63 m • Maximum elevation: 38 m

Mount Greylock via Bellows Pipe Trail in Mount Greylock State Reservation

United States > Massachusetts > Berkshire County > Adams

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: 683 m • Maximum elevation: 1,062 m

Mount Watatic and Nutting Hill Loop via Wapack Trail, Mid State Trail and State Line Trail in Watatic Mountain Wildlife Sanctuary

United States > Massachusetts > Worcester County > Ashburnham

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: 203 m • Maximum elevation: 545 m

Mount Norwottuck Loop via NET/M&M Trail, Horse Cave and Robert Frost Trail in Mount Holyoke Range State Park

United States > Massachusetts > Hampshire County > Amherst

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: 198 m • Maximum elevation: 318 m

Skyline and Reservoir Loop Trail in Middlesex Fells Reservation

United States > Massachusetts > Middlesex County > Medford

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: 167 m • Maximum elevation: 79 m

Skyline Trail, Sawcut Notch Path and Headquarters Path Loop in Blue Hills Reservation

United States > Massachusetts > Norfolk County > Quincy

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: 166 m • Maximum elevation: 138 m

Mount Wachusett Loop via Bolton Pond Trail, Old Indian and Semuhenna Trail in Wachusett Mountain State Reservation

United States > Massachusetts > Worcester County > Westminster

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: 308 m • Maximum elevation: 607 m

Rock Circuit Loop Trail via Boojum Rock, Ziggy's Rock, Pinnacle Rock, Black Rock and Melrose Rock in Middlesex Fells Reservation

United States > Massachusetts > Middlesex County > Medford

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: 102 m • Maximum elevation: 83 m

Eliot Tower and Great Blue Hill Loop via Skyline Trail in Blue Hills Reservation

United States > Massachusetts > Norfolk County > Milton

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: 226 m • Maximum elevation: 187 m

Noanets Woodlands Loop from Newton via Hale Rocky Woods, Snow Hill and Dover

United States > Massachusetts > Middlesex County > Newton

Distance: 22.8 mi • Elevation gain: 344 m • Maximum elevation: 112 m

Great River Ride, Gravel Route

United States > Massachusetts > Hampden County > Westfield

Distance: 73.1 mi • Elevation gain: 2,106 m • Maximum elevation: 484 m

Weston and Waltham trails

United States > Massachusetts > Middlesex County > Weston

Distance: 14.1 mi • Elevation gain: 292 m • Maximum elevation: 137 m

Summit Alt & Downspout

United States > Massachusetts > Franklin County > Sunderland

Mount Toby State Forest Trail Running

Distance: 6.2 mi • Elevation gain: 247 m • Maximum elevation: 274 m

Mount Toby Loop Trail Run

United States > Massachusetts > Franklin County > Sunderland

Sunderland Trail Running

Distance: 10.6 mi • Elevation gain: 435 m • Maximum elevation: 325 m

2024 Bikes Not Bombs Bike-a-thon (BAT) Agony & Ecstasy

United States > Massachusetts > Suffolk County > Boston

Distance: 106.4 mi • Elevation gain: 1,714 m • Maximum elevation: 183 m

Summit Bypass & Hidden Hill Upper

United States > Massachusetts > Franklin County > Sunderland

Mount Toby State Forest Trail Running

Distance: 9.0 mi • Elevation gain: 377 m • Maximum elevation: 273 m

Borderland Park Loop

United States > Massachusetts > Norfolk County > Sharon

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. #Hike #Loop #Park #Nature #Lake #Forest

Distance: 5.9 mi • Elevation gain: 81 m • Maximum elevation: 97 m

Medford Trails

United States > Massachusetts > Norfolk County > Needham

Medford/Dover trails

Distance: 26.9 mi • Elevation gain: 439 m • Maximum elevation: 122 m

Mount Greylock

United States > Massachusetts > Berkshire County > Adams

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. #Hike #Mountain #Nature #Forest #Appalachian

Distance: 5.6 mi • Elevation gain: 729 m • Maximum elevation: 1,062 m

Needham Town Forest

United States > Massachusetts > Middlesex County > Newton

Afternoon Ride

Distance: 12.2 mi • Elevation gain: 193 m • Maximum elevation: 65 m

Westville Conservation Area Loop

United States > Massachusetts > Bristol County > Taunton > Westville

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

Distance: 3.8 mi • Elevation gain: 23 m • Maximum elevation: 16 m

Hockomock Swamp

United States > Massachusetts > Plymouth County > Bridgewater

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

Distance: 2.3 mi • Elevation gain: 14 m • Maximum elevation: 25 m

Cutler Park Reservation Loop

United States > Massachusetts > Middlesex County > Newton

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. #Hike #Loop #Nature #Forest #River #City

Distance: 10.3 mi • Elevation gain: 108 m • Maximum elevation: 49 m

Gravel Bike City Square Park

United States > Massachusetts > Suffolk County > Boston

Distance: 1.4 mi • Elevation gain: 8 m • Maximum elevation: 12 m

Dover Trails (Dover, MA)

United States > Massachusetts > Middlesex County > Newton

Distance: 30.1 mi • Elevation gain: 466 m • Maximum elevation: 122 m

Town Forest, Rocky Narrows and Pegan Hill Reservation Loop MTB from Wellesley

United States > Massachusetts > Norfolk County > Wellesley

Distance: 17.7 mi • Elevation gain: 321 m • Maximum elevation: 122 m

Hammond Pond Reservation loop

United States > Massachusetts > Middlesex County > Newton

Distance: 1.9 mi • Elevation gain: 19 m • Maximum elevation: 71 m

Lynn woods

United States > Massachusetts > Essex County > Lynn

Distance: 1.5 mi • Elevation gain: 64 m • Maximum elevation: 81 m

Gravel Bike Sennot Park

United States > Massachusetts > Middlesex County > Cambridge

Distance: 2.7 mi • Elevation gain: 16 m • Maximum elevation: 11 m

Westford Town Tour

United States > Massachusetts > Middlesex County > Lexington

Distance: 67.0 mi • Elevation gain: 991 m • Maximum elevation: 124 m

Fire Road trails (mostly) in Weston

United States > Massachusetts > Middlesex County > Newton

Distance: 28.3 mi • Elevation gain: 416 m • Maximum elevation: 108 m

Rest of the Deer Path Conservation Area

United States > Massachusetts > Middlesex County > Weston

Weston Trails

Distance: 8.6 mi • Elevation gain: 119 m • Maximum elevation: 101 m

Medfield/Dover

United States > Massachusetts > Middlesex County > Newton

More exploring

Distance: 55.7 mi • Elevation gain: 785 m • Maximum elevation: 105 m

Weston Trails and Pine Street Forest

United States > Massachusetts > Middlesex County > Newton

Weston Trails, lots of areas including Dear Path Conservation Area

Distance: 30.4 mi • Elevation gain: 490 m • Maximum elevation: 108 m

Dedham-Providence-Dedham

United States > Massachusetts > Norfolk County > Dedham

Distance: 126.0 mi • Elevation gain: 1,811 m • Maximum elevation: 167 m

F. Gilbert Hills State Forest

United States > Massachusetts > Norfolk County > Foxborough > North Foxboro

Mountain Bike F. Gilbert Hills State Forest

Distance: 19.1 mi • Elevation gain: 268 m • Maximum elevation: 103 m

Trails around Newton/Weston/Wellesley

United States > Massachusetts > Middlesex County > Newton

Newton Trails

Distance: 16.3 mi • Elevation gain: 247 m • Maximum elevation: 88 m

The Trails of Groton with 3k Dirt in Lincoln/Lexington (Arlington Start)

United States > Massachusetts > Middlesex County > Arlington

Distance: 69.2 mi • Elevation gain: 1,034 m • Maximum elevation: 109 m

Dartmouth to Sakonnet Point

United States > Massachusetts > Bristol County > Dartmouth > Apponagansett

Distance: 22.9 mi • Elevation gain: 288 m • Maximum elevation: 53 m