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Green Markers |
Difficulty

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Length: 6.44 Miles
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This trail circles the three Winchester Reservoirs. It is mostly Fire Roads, except a few areas where there are no Fire Roads available. Its a fun little trail if you're in for a low key, relaxing ride. It has it's share of hills, just make sure you keep your eyes open, there are some blind corners.
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Skyline Trail
White Markers |
Difficulty

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Length: 7.88 Miles
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The Trail follows the outer perimeter of the western Fells. There are spectacular views of Boston and the surrounding area. Most of the Skyline trail is in wooded landscape, with several steep ascents to rocky outcrops.
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Reservoir Trail
Orange Markers |
Difficulty

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Length: 5.94 Miles
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This trail encircles the north, middle and south reservoirs and the open water can be seen from many sites (the reservoirs are for drinking water, so access to them is prohibited).
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Cross Fells Trail
Blue Markers |
Difficulty

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Length: 4.93 Miles
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Beginning in the western Fells near the Medford High School, the Cross Fells trail gives a good sampling of the features of the park, from wetlands at Whitmore Brook to open water at Quarter Mile Pond in the eastern Fells, to views at Carin Hill.
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Rock Circuit Trail
White Markers |
Difficulty

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Length: [?]
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Much of the trail traverses rocky outcrops in this corner of the park, providing a variety of scenic views.
ROCK Circuit Trail
It's more than a trail, its a Nemesis
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The Winchester Reservoir Trails
Not Marked & Off Limits |
Difficulty

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These trails circle the Winchester Reservoirs. They are on Winchester Water Works property and are CLOSED to everyone. They are constantly changing and are not marked, so they have no exact location or length.
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