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Skyline Trail

Intermediate/Difficult
 4.2 (33) RECOMMENDED ROUTE

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


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Map Key

7.5

Miles

12.1

KM

Loop

276' 84 m

High

114' 35 m

Low

846' 258 m

Up

863' 263 m

Down

4%

Avg Grade (2°)

19%

Max Grade (11°)

Dogs Leashed

Features Birding · Fall Colors · Views · Wildlife

Open dawn to dusk. Check with the

Overview

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.

Description

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.

Contacts

Shared By:

Trevor Wellman

Trail Ratings

  4.2 from 33 votes

#307

Overall
  4.2 from 33 votes
5 Star
48%
4 Star
27%
3 Star
21%
2 Star
3%
1 Star
0%
Recommended Route Rankings

#307

Overall
264 Views Last Month
23,460 Since Aug 8, 2016
Intermediate/Difficult

4%
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15%
27%
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Photos

Middlesex Fells, Medford, United States
Feb 19, 2020 near Winchester, MA
Middlesex Fells, Medford, United States
Feb 19, 2020 near Winchester, MA
Middlesex Fells Reservation
Feb 19, 2020 near Medford, MA
short-coated brown dog
Feb 19, 2020 near Stoneham, MA
sunlight passing thru trees
Feb 19, 2020 near Winchester, MA
An autumn view of Boston from the Fells
Feb 19, 2020 near Medford, MA

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Weather


Current Trail Conditions

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All Clear 52 days ago See History
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Check-Ins

Apr 18, 2021
Shanshan Liu
Apr 18, 2021
Shanshan Liu
Mar 24, 2021
Niels Volkerts
Mar 22, 2021
Gabriella Frongillo
Mar 18, 2021
Kevin H
Dec 6, 2020
Anita Parker
3.3mi
Aug 9, 2020
Alessandra Seiter
7.5mi — 3h 00m
Aug 8, 2020
Gabriel Vasquez-Billin
Didn't bring any food or enough water. Dumb. 7.6mi — 8h 36m