more stats
1.4 miles
Distance
355 ft
Climb
-200 ft
Descent
00:19:17
Avg time
154 ft
Altitude change
429 ft
Altitude min
590 ft
Altitude max
429 ft
Altitude start
583 ft
Altitude end
2.109%
Grade
-29.761%
Grade max
48.207%
Grade min
3,288 ft
Distance climb
2,459 ft
Distance down
1,545 ft
Distance flat
00:19:17
Avg time

The Darkside Details

  • Activities
    • Mountain Bike
    • Hike
    • Trail Running
  • Riding Area
    Rockland Preserve
    Madison, Connecticut
  • Difficulty Rating
  • Local Popularity
    85 in Mountain Biking [+]
    • 60 in Trail Running
    • 5 in Hiking
  • Global Ranking
    #48879 in Mountain Biking [+]
    • #147234 in Trail Running
    • #296328 in Hiking
  • State Ranking
    #333 in Mountain Biking · Connecticut [+]
    • #1,858 in Trail Running
    • #5,184 in Hiking
  • Blaze Color
  • Trail Type
    Singletrack
  • Direction
    One Direction
    Popular Direction Shown
  • Dogs Allowed
    Yes
  • eBike Allowed

No community description for The Darkside trail has been added yet!

AI Generated Description

The Darkside is a highly rated 1 mile popular blue difficulty singletrack trail located near Madison Connecticut. It has jumps and skinnies. This mountain bike primary trail can be used one direction. On average it takes 19 minutes to complete this trail.

Tags
JumpsSkinnies

Local Trail Association

Traditionally Indigenous Territory

Recent Activity on Trail

Past Week
  • 2 rides
  • 8 miles average
6 Months
  • 99 rides
  • 11 miles avg distance
All
  • 896 rides
  • Last: Oct 30, 2026
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The Darkside Trail Reports

statusdatedescription
Jul 19, 2026 @ 12:23pm (America/New_York)
Jul 19, 2026
Large tree down across trail, blocking trail. At the first right hand switch back after climbing the first large s section of dark side
Jun 25, 2023 @ 5:24am
Jun 25, 2023
Jun 25, 2023 @ 5:23am
Jun 25, 2023
Muddy after the rain; 2 trees are down
May 6, 2023 @ 3:02pm
May 6, 2023
Dec 26, 2022 @ 10:37am
Dec 26, 2022
Tree down. Small, ~12” off of ground.
more »
Status:
on Jul 19, 2026
Avg: 4.07 (8 votes)
Your vote: 0

view (3,669)
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      Directions to the-darkside trailhead (41.430970, -72.656140)

      Photos

      4 more »
      mtb
      20 |
      Oct 24, 2026 @ 7:23pm
      Oct 24, 2026
      report
      mtb
      31 |
      Jul 19, 2026 @ 12:51pm
      Jul 19, 2026
      report
      mtb
      30 |
      Jul 19, 2026 @ 9:24am
      Jul 19, 2026
      report
      mtb
      58 |
      Jun 25, 2023 @ 5:24am
      Jun 25, 2023

      Videos

      no videos have been added for The Darkside yet, add a video.

      Routes with this trail

      ★ 5.0 • 18 miles • 1,823 ft • 20 • Loop •
      Advanced Rockland loop from the Rt.79 lot with Northern Exposure.
      ★ 5.0 • 17 miles • 1,759 ft • 34 •
      This epic ride ties in many of the great parts of Rockland in this 17 miler. 4 climbs to the Summit area...
      15 miles • 1,608 ft • 20 •
      Personal ride around Rockland Preserve.
      4.2 ★★★★★
      8 Ratings
      5 ★ 50%
      4 ★ 25%
      3 ★ 13%
      2 ★ 13%
      1 ★

      1 Review & Comments

      dvining
      Relatively easy with short challenging climbs.

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      Frequently Asked Questions

      ▼ Where is The Darkside located?
      The Darkside is located in Rockland Preserve, Madison, Connecticut, United States. It is part of the Rockland Preserve trail network. The trailhead is located at coordinates 41.43097, -72.65614.
      ▼ How hard is The Darkside?
      The Darkside is rated as Blue difficulty. The average grade is 2.109%.
      ▼ What is the elevation gain for The Darkside?
      The Darkside has 355 ft of elevation gain. The trail has 200 ft of elevation descent. The elevation ranges from 429 ft to 590 ft.
      ▼ Is The Darkside a point to point trail?
      Yes, The Darkside is a point to point trail. The direction is One Direction. The trail type is singletrack.
      ▼ How long is The Darkside?
      The Darkside is 1.4 miles long. The trail type is singletrack.
      ▼ Are dogs allowed on The Darkside?
      Yes, dogs are allowed on The Darkside. Please keep dogs on a leash where required and clean up after them.
      ▼ When is the best time of year to ride The Darkside?
      Based on activity log data, the most popular months to ride The Darkside are:
      • August (42 activities)
      • September (39 activities)
      • June (36 activities)
      Check the reports page for current trail conditions.
      ▼ How do I access The Darkside? Where is the closest parking trailhead?
      The closest parking and trailhead locations to The Darkside are: View all parking locations in the area.
      ▼ How long does it take to ride The Darkside?
      Based on recorded activities, it takes an average of 19 minutes to ride The Darkside. The trail is 1.4 miles long. Actual times will vary based on fitness level, conditions, and pace. View recent activity logs for more details.
      ▼ How busy is The Darkside?
      The Darkside is a very popular trail. There have been 3,384 recorded activities on this trail. The trail has received 3,669 check-ins. View recent activity on this trail.

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