more stats
4,540 ft
Distance
21 ft
Climb
-32 ft
Descent
00:04:57
Avg time
-11 ft
Altitude change
31 ft
Altitude min
55 ft
Altitude max
46 ft
Altitude start
35 ft
Altitude end
-0.238%
Grade
-7.13%
Grade max
4.069%
Grade min
1,984 ft
Distance climb
1,813 ft
Distance down
743 ft
Distance flat
00:04:57
Avg time

Pennywise Path Details

  • Activities
    • Mountain Bike
    • E-Bike
    • Hike
    • Trail Running
  • Riding Area
    Edgartown
    , Massachusetts
  • Difficulty Rating
    Green Rate
  • Local Popularity
    65 in Mountain Biking [+]
    • 5 in E-Biking
    • 5 in Trail Running
    • 5 in Hiking
  • Global Ranking
    #170556 in Mountain Biking [+]
    • #27224 in E-Biking
    • #69796 in Trail Running
  • Hiking SAC Scale
    T1 Hiking
  • Trail Type
    Singletrack
  • Bike Type
    XC
  • Direction
    Both Directions
  • Climb Difficulty
    Green
  • Physical Rating
    Easy
  • Trail Visibility
    Always easy to follow
  • Dogs Allowed
    Yes
  • eBike Allowed
    Yes up to Class 1
  • Ride in Rain
    Yes

Wide single track trail which dates back to 1800s. Runs from end of Pennywise Path dirt road to the 4-way intersection on north side of Pennywise Preserve. Often used as a segment of a non-paved route from Edgartown to the State Forest. Sandy in places.

Local Trail Association
Traditionally Indigenous Territory

Recent Activity on Trail

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6 Months
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All
  • 7 rides
  • Last: Jun 28, 2026
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  • Snow Cover Partial
  • Freeze/thaw Cycle
  • Icy
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  • Variable
  • Ideal
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        Directions to pennywise-path trailhead (41.402370, -70.563920)

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        Frequently Asked Questions About Pennywise Path

        ▼ Where is Pennywise Path located?
        Pennywise Path is located in Edgartown, Massachusetts, United States. It is part of the Edgartown trail network. The trailhead is located at coordinates 41.40237, -70.56392.
        ▼ How hard is Pennywise Path?
        Pennywise Path is rated as Green difficulty. The physical rating is Easy. The average grade is 0.238%. The climb difficulty is rated Green.
        ▼ What is the elevation gain for Pennywise Path?
        Pennywise Path has 21 ft of elevation gain. The trail has 32 ft of elevation descent. The elevation ranges from 31 ft to 55 ft.
        ▼ Is Pennywise Path a point to point trail?
        Pennywise Path is not a point to point trail. The direction is Both Directions. The trail type is singletrack.

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