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Pine Hill, Wenepoykin Hill
Medford, MA
Trailheads, measurements, times, distances, and maps are all approximate and relative to the hike(s) as shown below.

The Skyline Trail on Pine Hill
Route: Herd path, Quarry Road, Skyline Trail, Cross Fells Trail, Red Cross Path, Middle Road
Quick jog in the southern Middlesex Fells.
Trails were generally dry with occasional minor frost-melt mud and a few tiny patches of ice. Nice views from Wright Tower on Pine Hill and on Wenepoykin with the leaves down. Highly recommend having a map handy (had one saved on my phone), as there are all sorts of trails and junctions.
Hike Ratings |
Getting To Trailhead: |
Easy |
Destination: |
Pine Hill |
Length: |
Easy |
Steepness: |
Moderate |
Navigation: |
Moderate |
Views: |
Excellent |
Crowds: |
Heavy |
Destination: |
Wenepoykin Hill |
Length: |
Easy |
Steepness: |
Moderate |
Navigation: |
Moderate |
Views: |
Excellent |
Crowds: |
Moderate |
|
Hike Stats |
Date Hiked: |
Sunday, November 23, 2014 |
Parking Elevation: |
110' |
Destination: |
Pine Hill |
Time Elapsed: |
00:06 |
Trailhead Elevation: |
90' |
Summit Elevation: |
243' |
Vertical Gain: |
153' |
Destination: |
Wenepoykin Hill |
Time Elapsed: |
00:15 |
Trailhead Elevation: |
243' |
Summit Elevation: |
225' |
Vertical Gain: |
155' |
Hike Time Elapsed: |
00:42 |
Hike Vertical Gain: |
348' |
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The start of the old ski area access road off Bennett Road
Looking at Boston from Wright's Tower on Pine Hill

Nearing Wenepoykin Hill on the Skyline Trail
Looking southeast from Wenepoykin Hill


Directions to trailhead: From Interstate 93 near Medford, take Exit 33, then take Route 28 north to a traffic circle, then head west on South Border Road. There are multiple small roadside parking areas in the vicinity of Bellevue Pond.
Back to Pine Hill Profile
Back to Wenepoykin Hill Profile
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