Middlesex County trails
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Mount Gilboa
United States > Massachusetts > Middlesex County > Arlington
Distance: 0.7 mi • Elevation gain: 102 ft • Maximum elevation: 276 ft

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: 335 ft • Maximum elevation: 272 ft

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: 548 ft • Maximum elevation: 259 ft

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: 1,129 ft • Maximum elevation: 367 ft

Weston and Waltham trails
United States > Massachusetts > Middlesex County > Weston
Distance: 14.1 mi • Elevation gain: 958 ft • Maximum elevation: 449 ft

Needham Town Forest
United States > Massachusetts > Middlesex County > Newton
Afternoon Ride
Distance: 12.2 mi • Elevation gain: 633 ft • Maximum elevation: 213 ft

Dover Trails (Dover, MA)
United States > Massachusetts > Middlesex County > Newton
Distance: 30.1 mi • Elevation gain: 1,529 ft • Maximum elevation: 400 ft

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. #Hiking #Loop #Nature #Forest #River #City
Distance: 10.3 mi • Elevation gain: 354 ft • Maximum elevation: 161 ft

Hammond Pond Reservation loop
United States > Massachusetts > Middlesex County > Newton
Distance: 1.9 mi • Elevation gain: 62 ft • Maximum elevation: 233 ft

Fire Road trails (mostly) in Weston
United States > Massachusetts > Middlesex County > Newton
Distance: 28.3 mi • Elevation gain: 1,365 ft • Maximum elevation: 354 ft

Gravel Bike Sennot Park
United States > Massachusetts > Middlesex County > Cambridge
Distance: 2.7 mi • Elevation gain: 52 ft • Maximum elevation: 36 ft

Westford Town Tour
United States > Massachusetts > Middlesex County > Lexington
Distance: 67.0 mi • Elevation gain: 3,251 ft • Maximum elevation: 407 ft

Rest of the Deer Path Conservation Area
United States > Massachusetts > Middlesex County > Weston
Weston Trails
Distance: 8.6 mi • Elevation gain: 390 ft • Maximum elevation: 331 ft

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: 1,608 ft • Maximum elevation: 354 ft

Medfield/Dover
United States > Massachusetts > Middlesex County > Newton
More exploring
Distance: 55.7 mi • Elevation gain: 2,575 ft • Maximum elevation: 344 ft

Trails around Newton/Weston/Wellesley
United States > Massachusetts > Middlesex County > Newton
Newton Trails
Distance: 16.3 mi • Elevation gain: 810 ft • Maximum elevation: 289 ft

The Trails of Groton with 3k Dirt in Lincoln/Lexington (Arlington Start)
United States > Massachusetts > Middlesex County > Arlington
Distance: 69.2 mi • Elevation gain: 3,392 ft • Maximum elevation: 358 ft

Noon Hill and other Medford Trails
United States > Massachusetts > Middlesex County > Newton
Exploring Medfield
Distance: 47.0 mi • Elevation gain: 2,510 ft • Maximum elevation: 344 ft

Charles River Trails in Watertown, Newton, Cambridge, Boston
United States > Massachusetts > Middlesex County > Newton
River Ride, both sides
Distance: 16.4 mi • Elevation gain: 545 ft • Maximum elevation: 46 ft

Rocky Narrows area
United States > Massachusetts > Middlesex County > Newton
More investigations
Distance: 46.0 mi • Elevation gain: 2,188 ft • Maximum elevation: 344 ft

Various trails in Dover, Medfied, Needham area
United States > Massachusetts > Middlesex County > Newton
Distance: 49.0 mi • Elevation gain: 2,536 ft • Maximum elevation: 400 ft

Noanet, Caryl Woods, Blake Conservation Land, Chickering School
United States > Massachusetts > Middlesex County > Newton
Wandering
Distance: 21.6 mi • Elevation gain: 1,060 ft • Maximum elevation: 220 ft

Loop in Eastern Mass involving various rail trails
United States > Massachusetts > Middlesex County > Newton
Distance: 126.6 mi • Elevation gain: 6,365 ft • Maximum elevation: 636 ft

Rocky Woods, Hale, Rosemary Pond
United States > Massachusetts > Middlesex County > Newton
Rocky Woods
Distance: 41.3 mi • Elevation gain: 1,886 ft • Maximum elevation: 348 ft

Walden Pond Loop
United States > Massachusetts > Middlesex County > Concord
Distance: 1.9 mi • Elevation gain: 135 ft • Maximum elevation: 207 ft

Wellesley wandering
United States > Massachusetts > Middlesex County > Newton
Some Wellesley trails
Distance: 41.4 mi • Elevation gain: 2,005 ft • Maximum elevation: 348 ft

Medford trails
United States > Massachusetts > Middlesex County > Newton
Distance: 46.0 mi • Elevation gain: 2,244 ft • Maximum elevation: 308 ft

BruceFreemen and MCRT in Sudbury
United States > Massachusetts > Middlesex County > Newton
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

Hudson Snack Loop
United States > Massachusetts > Middlesex County > Medford > West Medford
Assabat River Trail Hudson -> Maynard
Distance: 64.4 mi • Elevation gain: 2,415 ft • Maximum elevation: 459 ft

Cambridge - Providence Express
United States > Massachusetts > Middlesex County > Cambridge
Alewife -> Providence
Distance: 63.2 mi • Elevation gain: 3,153 ft • Maximum elevation: 351 ft

BELLEVUE
United States > Massachusetts > Middlesex County > Medford
Bike Loop Bellevue
Distance: 7.0 mi • Elevation gain: 413 ft • Maximum elevation: 289 ft

ASP QUARRY
United States > Massachusetts > Middlesex County > Ashland
Quarry Route in Ashland
Distance: 1.8 mi • Elevation gain: 135 ft • Maximum elevation: 344 ft