Middlesex Fells Reservation - Hiking

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Just outside of Boston, Middlesex Fells Reservation combines the backwoods experience with the accessibility on which city-dwellers rely. The reservation's Skyline Trail offers city views, varied terrain, and strenuous trails .

Written by

Allie Aylward


6.9 miles

Destination Distance From Downtown

6.9 miles


4 of 5 diamonds

Its length and topography makes Skyline Trail one of the more difficult trails in Middlesex Fells Reservation.

Time To Complete

4 hours

Allow at least 4 hours to complete Skyline Trail. At a brisk pace and with minimal breaks, hikers can reasonably complete the trek in 3 hours, but beginners should budget as much as 5 hours to hike the whole loop.


All Seasons

Middlesex Fells Reservation is open year round and, frankly, enjoyable year round. Skyline Trail may be a bit more strenuous after a large snowfall, but its rocky and, at times, uneven terrain will be covered and hikers less likely to trip.

Dog Friendly


Dogs are permitted on leash on the trails at Middlesex Fells, but are allowed to play off leash in the designated dog park near the parking lot.



Created in 1894 on land deemed “too wild to have been farmed,” Middlesex Fells Reservation was known then for its embrace of the area’s natural topography. Even today, trails inside the reservation don’t fight against the natural landscape, but rather work around it in a conscious act of preservation.

A short drive from Boston, Medford's Middlesex Fells Reservation offers city-dwellers quiet respite from the urban bustle by combining the backwoods experience with accessibility to the Greater Boston Area. Its 2,575 acres contains 10 different trails of that range from 0.2 to 9.0 miles in length. The reservation's crown jewel, Skyline Trail, offers city skyline views, varied terrain, and strenuous trails -- all markers of a great day hike.

What Makes It Great

Many trails accessible to urbanites lack the length and difficulty to really feel like a hike; Skyline Trail at Middlesex Fells Reservation is not one of these. Don't let its proximity to Boston fool you. So, whereas experienced hikers may not feel challenged at Blue Hills or Hale Reservations, Skyline Trail is where things finally get interesting. You'll want to make sure you wear your trustiest hiking boots.

Skyline Trail leads around the outer perimeter of the western half of Middlesex Fells, allowing hikers to experience a wide range of the reservation's features. Depending on the starting point, the trail's points of interest fall within the first or last 2.5 miles of the hike. This brief portion of the trail boasts Wright's Tower and the rocky outcrop, Panther Cave. Hikers are likely to encounter the most trail traffic around these sites. 

The remaining 5 miles of Skyline Trail leads hikers through aged coniferous and deciduous forests, with a brief section that directly borders North Reservoir. It is in these areas that the natural beauty of The Fells is truly evident. 

Who is Going to Love It

Dog owners, experienced and beginner hikers, and city-dwellers

With a designated area for dogs to play freely, Middlesex Fells is incredibly popular for dog owners. The Sheepfold Dog Park is a large, grassy meadow with picnic tables and seating areas. Dog owners should note that pets off leash must be able to follow verbal commands so as not to disturb other park visitors. 

Both experienced and beginner hikers will enjoy exploring Middlesex Fells Reservation, as well. Those seeking a more strenuous hike should opt for Skyline, Rock Circuit, or Cross Fells Trails. For an easier trek, choose trails such as Reservoir and Crystal Spring Trails.

A few words to new hikers that decide tackle Skyline Trail: allow 5+ hours, bring plenty of water, and pay attention to the white trail blazes. Even as an attentive hiker, I found myself pausing at more than a few intersections to verify I was walking the right way. Several portions of Skyline Trail intersect with Reservoir Trail, marked with orange blazes, and the Mountain Bike Loop, marked with green blazes. When these trails converge, all three trail blazes will appear together. So, if you see an orange and a green blaze but not a white one, you're headed in the wrong direction.

Directions, Parking, & Regulations

Two main parking lots are located at the Sheepfold trailhead off Route 28 and I-93 N. Smaller lots, which are labeled on the trail map, provide easier access to specific portions of the reservation. 

It's a straight shot along I-93 N to get to Middlesex Fells Reservation from downtown Boston. Take exit 33, merge onto MA-28 N/Fellsway W and continue on MA-28. The reservation entrance will be on the left.

To reach Middlesex Fells via public transit, hikers have a few options. First is the Orange Line to Wellington then the 134 Bus  to Winthrop St. at Playstead Rd., which gets you 1.1 miles from the parking lot. An alternative is to take the Red Line to Davis Square, then board the 94 bus to High St. at Winthrop Circle, then transfer to the 134 Bus and get off at Main St. at Chestnut St. This gets you 0.6 miles from the trailhead. Lastly, hikers can take the Lowell Commuter Rail Line from North Station to Wedgemere, and then walk 1.1 miles to the trailhead.

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Middlesex Fells Reservation

Medford, MA, 02155
42.451979, -71.104715

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