more stats
2,133 ft
Distance
62 ft
Climb
-41 ft
Descent
407 ft
High Point
22 ft
Altitude change
357 ft
Altitude min
357 ft
Altitude start
381 ft
Altitude end
1%
Grade
-18.6%
Grade max
18.4%
Grade min
1,125 ft
Distance climb
659 ft
Distance down
348 ft
Distance flat

Winner Winner Details

  • Activities
    • Mountain Bike
    • E-Bike
    • Hike
    • Trail Running
  • Riding Area
    Maple Wind Farm
    Richmond, Vermont
  • Difficulty Rating
  • Local Popularity
    75 in Mountain Biking [+]
    • 90 in E-Biking
    • 50 in Trail Running
    • 100 in Hiking
  • Global Ranking
    #6210 in Mountain Biking [+]
    • #101824 in E-Biking
    • #150022 in Trail Running
    • #73054 in Hiking
  • State Ranking
    #72 in Mountain Biking · Vermont [+]
    • #515 in E-Biking
    • #1,266 in Trail Running
    • #579 in Hiking
  • Hiking SAC Scale
    T1 Hiking
  • Trail Type
    Singletrack
  • Bike Type
    AM, XC
  • Direction
    Both Directions
  • Climb Difficulty
    Blue
  • Physical Rating
    Moderate
  • Trail Visibility
    Always easy to follow
  • Family Friendly
    Yes
  • Dogs Allowed
    Yes
  • eBike Allowed
    Yes up to Class 1
  • TTFs on Trail
    Bridge, Rock Face, Roller Coaster
  • Year Opened
    2025

Starting at the Maple Wind Farm store and trailhead parking, the connector enters just past the farm gate before cutting into the woods. A short benched section leads riders across a small stream and into loamy forest, which quickly transitions into very rocky ground along the base of a cliff wall. The route winds through chunky terrain, climbing over a stone ramp and weaving between trees. From there, the trail crosses a larger stream via a wooden bridge, then transitions onto an old logging road. This road serves as the approach to the "Chicken Dinner" climbing trail, providing a direct link from the farm to the main trail network.

Trail Supporters
Local Trail Association
Traditionally Indigenous Territory

Recent Activity on Trail

Past Week
  • 6 rides
  • 5 miles average
6 Months
  • 96 rides
  • 7 miles avg distance
All
  • 184 rides
  • Last: Oct 3, 2026
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update trails status or condition

Winner Winner Trail Reports

statusdatedescription
Aug 29, 2026 @ 12:13pm (America/New_York)
Aug 29, 2026
Really dry and good conditions.
Jul 22, 2026 @ 9:47pm (America/New_York)
Jul 22, 2026
reporter Dry summer conditions.
Jun 25, 2026 @ 7:34am (America/New_York)
Jun 25, 2026
Jun 18, 2026 @ 1:38pm (America/New_York)
Jun 18, 2026
reporter Big Rain. Needs time to dry.
Jun 8, 2026 @ 11:58am (America/New_York)
Jun 8, 2026
reporter Trails may be soft. Turn back if too wet
more »
Status:
on Aug 29, 2026
Ideal
Avg: 4.29 (4 votes)
Your vote: 0

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      Directions to winner-winner trailhead (44.400490, -72.973190)

      Photos

      41 more »
      mtb
      128 |
      Sep 17, 2025 @ 2:20am
      Sep 17, 2025
      mtb
      97 |
      Sep 12, 2025 @ 7:51pm
      Sep 12, 2025
      mtb
      3 |
      Sep 30, 2026 @ 12:21pm
      Sep 30, 2026
      mtb
      3 |
      Sep 30, 2026 @ 12:21pm
      Sep 30, 2026

      Videos

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      1 Review & Comments


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      • By JakeSaltzTF Pro MWF & contributors
      • #859930 - 510 views

      Frequently Asked Questions

      ▼ Where is Winner Winner located?
      Winner Winner is located in Maple Wind Farm, Richmond, Vermont, United States. It is part of the Maple Wind Farm trail network. The trailhead is located at coordinates 44.40049, -72.97319.
      ▼ How hard is Winner Winner?
      Winner Winner is rated as Blue difficulty. The physical rating is Moderate. The average grade is 1%. The climb difficulty is rated Blue.
      ▼ What is the elevation gain for Winner Winner?
      Winner Winner has 62 ft of elevation gain. The trail has 41 ft of elevation descent. The elevation ranges from 357 ft to 407 ft.
      ▼ Is Winner Winner a point to point trail?
      Winner Winner is not a point to point trail. The direction is Both Directions. The trail type is singletrack.
      ▼ How long is Winner Winner?
      Winner Winner is 2,133 ft long. The trail type is singletrack.
      ▼ Are dogs allowed on Winner Winner?
      Yes, dogs are allowed on Winner Winner. Please keep dogs on a leash where required and clean up after them.
      ▼ How do I access Winner Winner? Where is the closest parking trailhead?
      The closest parking and trailhead locations to Winner Winner are: View all parking locations in the area.
      ▼ How busy is Winner Winner?
      Winner Winner is a very popular trail. There have been 369 recorded activities on this trail. The trail has received 496 check-ins. View recent activity on this trail.

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