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Skyline Trail



7.5 mile 12.1 kilometer loop
93% Runnable


Ascent: 846' 258 m
Descent: -863' -263 m
High: 276' 84 m
Low: 114' 35 m


Avg Grade: 4% (2°)
Max Grade: 19% (11°)


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Trail shared by Trevor Wellman

The premier offering at the Middlesex Fells features surprising elevation and great views of Boston.

Trevor Wellman

Features Birding · Fall Colors · Views · Wildlife

Open dawn to dusk. Check with the


The best compliment you can give the Skyline Trail at the Fells is that you almost forget you're always comfortably nestled within the Boston suburbs and often parallel to some of the worst rush hour traffic New England has to offer.

Really though. Despite all the nearby hullabaloo (or perhaps somewhat because of it) the relative vastness and peacefulness of the Fells are endlessly remarkable. The continuous seven some-odd miles of mixed singletrack and doubletrack cross plenty of other trails, dart up and down countless rugged rocky outcrops, and wind into and out of typically suburban neighborhoods, and you'll likely see a greater variety of terrain than anywhere else in the state and possibly even anywhere else in New England.

Need to Know

Parking is available all around the Fells, but the easiest access is probably from the Sheepfold Lot. This lot and area, in general, can be crazy on weekends and in the after-work hours. Off-hours are best in the Fells for avoiding the very same sense of craziness you came to escape in the first place.


Even in ideal conditions, keep a good head about you if you want to remain on the white Skyline Trail proper, though it's generally easy to connect back to the trail or to follow the parallel orange Reservoir Trail or green Mountain Bike Loop if you get off course. Less-than-ideal conditions often make the trail more fun as they amplify the transient feelings of remoteness than can make the Fells so special.

One of the main highlights is Wright's Tower at the southeast corner. This outcrop, to me, embodies the Skyline Trail as a whole: you can at once see the Boston skyline and the dizzying traffic on I-93 below, and yet somehow feel like you're on top of a much larger, more remote hill.

Flora & Fauna

Deer, turkeys, etc.

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Oct 15, 2019
Brendan S
Good workout with diverse terrain. Pay attention to white trail markers, it's easy at points to lose the trail and it intersects with many others. 7.5mi
Sep 14, 2019
Patrick Smith
Jul 9, 2019
Chris Hauska
Jun 30, 2019
John Plunkett
Trail well marked with white blazes except for crossings where it is easy to veer off path. 7.5mi — 1h 15m
Nov 16, 2018
Geneva G
Jul 15, 2018
Lucas Hemenway
got lost several times at the beginning until I figured out that the white markers we're what I wanted. went clockwise which was probably a mistake… 7.8mi
May 18, 2018
Chi Wang
Apr 21, 2018
Chi Wang

Trail Ratings

  4.2 from 28 votes


  4.2 from 28 votes
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180 Views Last Month
16,968 Since Aug 8, 2016



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Mar 20, 2017 near Medford, MA
Barred Owl.
Aug 17, 2016 near Stoneham, MA
Beautiful day.
Sep 3, 2019 near Medford, MA
The sun sets over a late-winter landscape along the Skyline Trail.
Mar 20, 2017 near Medford, MA
North Reservoir's glassy water provides a beautiful view from the Skyline Trail.
Mar 20, 2017 near Winchester, MA
Middlesex Fells Cityscape from Wright's Tower
Oct 21, 2019 near Medford, MA


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