more stats
4,242 ft
Distance
75 ft
Climb
-22 ft
Descent
00:06:49
Avg time
53 ft
Altitude change
128 ft
Altitude min
195 ft
Altitude max
142 ft
Altitude start
197 ft
Altitude end
1.3%
Grade
-5.1%
Grade max
15.3%
Grade min
2,523 ft
Distance climb
1,522 ft
Distance down
197 ft
Distance flat
00:06:49
Avg time

Winch It Details

  • Activities
    • Mountain Bike
    • Hike
    • Trail Running
  • Riding Area
    Dogtown
    Gloucester, Massachusetts
  • Difficulty Rating
    Green Rate
  • Local Popularity
    90 in Mountain Biking [+]
    • 5 in Trail Running
    • 65 in Hiking
  • Global Ranking
    #160845 in Mountain Biking [+]
    • #66120 in Trail Running
    • #60827 in Hiking
  • Trail Type
    Singletrack
  • Direction
    Both Directions
  • Dogs Allowed
    Yes

This is a wide dirt path traversing the northern end of Dogtown. It runs from Norton Tree Farm to Johnson Road.
It crosses a lot of terrain, some of which is kind of technical, but overall it is a well-traveled beginner trail.

Most of the trail is in good shape, but between the intersections of High Street Extension and Town Line Trail South, there is a large water crossing with no clean way across.

Local Trail Association
Traditionally Indigenous Territory

Recent Activity on Trail

Past Week
  • 1 rides
  • 9 miles average
6 Months
  • 3 rides
  • 10 miles avg distance
All
  • 49 rides
  • Last: Jun 20, 2026
c1c2c3c4
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Trail Conditions
  • Unknown
  • Snow Groomed
  • Snow Packed
  • Snow Covered
  • Snow Cover Partial
  • Freeze/thaw Cycle
  • Icy
  • Prevalent Mud
  • Wet
  • Variable
  • Ideal
  • Dry
  • Very Dry
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  • Both Directions
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  • Uphill Only
  • One Direction
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        Directions to winch-it trailhead (42.663460, -70.648180)

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        Frequently Asked Questions About Winch It

        ▼ Where is Winch It located?
        Winch It is located in Dogtown, Gloucester, Massachusetts, United States. It is part of the Dogtown trail network. The trailhead is located at coordinates 42.66346, -70.64818.
        ▼ How hard is Winch It?
        Winch It is rated as Green difficulty. The average grade is 1.3%.
        ▼ What is the elevation gain for Winch It?
        Winch It has 75 ft of elevation gain. The trail has 22 ft of elevation descent. The elevation ranges from 128 ft to 195 ft.
        ▼ Is Winch It a point to point trail?
        Winch It is not a point to point trail. The direction is Both Directions. The trail type is singletrack.

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