more stats
2,280 ft
Distance
-24 ft
Descent
00:02:27
Avg time
-23 ft
Altitude change
163 ft
Altitude min
187 ft
Altitude max
187 ft
Altitude start
164 ft
Altitude end
-1%
Grade
-4.7%
Grade max
1.3%
Grade min
92 ft
Distance climb
1,198 ft
Distance down
935 ft
Distance flat
00:02:27
Avg time

Sheepfold Path Details

  • Activities
    • Mountain Bike
    • Hike
    • Trail Running
  • Riding Area
    Middlesex Fells Reservation
    Winchester, Massachusetts
  • AKA
    Orange Trail
  • Difficulty Rating
    Green Rate
  • Local Popularity
    100 in Mountain Biking [+]
    • 80 in Trail Running
    • 50 in Hiking
  • Global Ranking
    #21250 in Mountain Biking [+]
    • #5063 in Trail Running
    • #12291 in Hiking
  • Blaze Color
  • Trail Type
    Singletrack
  • Bike Type
    AM, XC
  • Direction
    Both Directions
    Popular Direction Shown
  • Climb Difficulty
    Green
  • Physical Rating
    Easy
  • Trail Visibility
    Always easy to follow
  • Dogs Allowed
    Yes
  • eBike Allowed
    No
  • Land Owner
    DCR

This is a simple, mostly flat trail that passes right through the dog park. There's a nice bridge at the end of the trail, too.

Local Trail Association
Traditionally Indigenous Territory

Recent Activity on Trail

Past Week
  • 9 rides
  • 10 miles average
6 Months
  • 325 rides
  • 9 miles avg distance
All
  • 2,033 rides
  • Last: Sep 19, 2026
c1c2c3c4
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update trails status or condition

Sheepfold Path Trail Reports

statusdatedescription
Sep 30, 2025 @ 2:45pm (America/New_York)
Sep 30, 2025
 Large tree down across trail, blocking trail. Requires walking over.
Sep 23, 2025 @ 10:03am (America/New_York)
Sep 23, 2025
Nov 16, 2023 @ 9:19am
Nov 16, 2023
Oct 23, 2023 @ 10:08am
Oct 23, 2023
Sep 26, 2023 @ 9:55am
Sep 26, 2023
more »
Status:
on Sep 30, 2025
Ideal
Avg: 3.99 (3 votes)
Your vote: 0

view (7,585)
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      Directions to sheepfold-path trailhead (42.457200, -71.108210)
      View on Discover Map

      Photos

      1 more »
      mtb
      371 |
      May 11, 2018 @ 12:23pm
      May 11, 2018

      Videos

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      Routes with this trail

      38
      MF Reservoir Trail Route (Orange Blazes)
      ★ 3.9 • 6 miles • 445 ft • 21 • Loop •
      This route starts from the Bear Hill Parking Area at 100 Fallon Rd, Stoneham, MA (off exit 35 Route 93)....
      64
      Fells Fun Loop for Today
      ★ 4.0 • 18 miles • 1,925 ft • 99 •
      test ride for today's ride
      65
      Fells Longer Ride, South Border
      18 miles • 1,893 ft • 102 •
      start and end from South Border

      Links

      4.0 ★★★★★
      3 Ratings
      5 ★
      4 ★ 100%
      3 ★
      2 ★
      1 ★

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      Nearby Trails

      Middlesex Fells Reservation

      • By RadiofaceTF Pro & contributors
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      Frequently Asked Questions

      ▼ Where is Sheepfold Path located?
      Sheepfold Path is located in Middlesex Fells Reservation, Winchester, Massachusetts, United States. It is part of the Middlesex Fells Reservation trail network. The trailhead is located at coordinates 42.4572, -71.10821.
      ▼ How hard is Sheepfold Path?
      Sheepfold Path is rated as Green difficulty. The physical rating is Easy. The average grade is 1%. The climb difficulty is rated Green.
      ▼ What is the elevation gain for Sheepfold Path?
      The trail has 24 ft of elevation descent. The elevation ranges from 163 ft to 187 ft.
      ▼ Is Sheepfold Path a point to point trail?
      Sheepfold Path is not a point to point trail. The direction is Both Directions. The trail type is singletrack.
      ▼ How long is Sheepfold Path?
      Sheepfold Path is 2,280 ft long. The trail type is singletrack.
      ▼ Are dogs allowed on Sheepfold Path?
      Yes, dogs are allowed on Sheepfold Path. Please keep dogs on a leash where required and clean up after them.
      ▼ How do I access Sheepfold Path? Where is the closest parking trailhead?
      The closest parking and trailhead locations to Sheepfold Path are: View all parking locations in the area.
      ▼ How long does it take to ride Sheepfold Path?
      Based on recorded activities, it takes an average of 3 minutes to ride Sheepfold Path. The trail is 2,280 ft long. Actual times will vary based on fitness level, conditions, and pace. View recent activity logs for more details.
      ▼ How busy is Sheepfold Path?
      Sheepfold Path is a very popular trail. There have been 7,564 recorded activities on this trail. The trail has received 7,585 check-ins. View recent activity on this trail.

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