more stats
2.0 miles
Distance
373 ft
Climb
-372 ft
Descent
00:12:36
Avg time
0 ft
Altitude change
1,191 ft
Altitude min
1,267 ft
Altitude max
1,195 ft
Altitude start
1,195 ft
Altitude end
0.001%
Grade
-23.637%
Grade max
21.386%
Grade min
4,670 ft
Distance climb
5,042 ft
Distance down
939 ft
Distance flat
00:12:36
Avg time

The Bobby Details

  • Activities
    • Mountain Bike
    • Hike
    • Trail Running
  • Riding Area
    Sidie Hollow Park
    Viroqua, Wisconsin
  • Difficulty Rating
  • Local Popularity
    60 in Mountain Biking [+]
    • 5 in Trail Running
    • 5 in Hiking
  • Global Ranking
    #90031 in Mountain Biking [+]
    • #353388 in Trail Running
    • #330013 in Hiking
  • State Ranking
    #662 in Mountain Biking · Wisconsin [+]
    • #2,103 in Trail Running
    • #2,119 in Hiking
  • Trail Type
    Singletrack
  • Bike Type
    XC
  • Direction
    Both Directions
  • Dogs Allowed
    Yes
  • Land Owner
    Vernon County Parks

The Bobby is known as one of the best segments of trail at Sidie Hollow, and is one of the best flow trails in all of southwestern Wisconsin. It provides about 200 feet of elevation change in its 2 miles. As the core of Sidie Hollow, The Bobby helps provide limitless ride combinations with its connections to Der Oberlken, Wind Up, Well Digger, Dang, Girl, and Bake Sale.

The Bobby is technically the first piece of trail that Vernon Trails built as well as the first legal piece of singletrack in Vernon County. It is regarded as an intermediate level trail but has seen many beginners getting hooked on mountain biking as well as many advanced riders enjoying the fast flow.

Tags
Flowy

Local Trail Association

Recent Activity on Trail

Past Week
  • 0 rides
  •  
6 Months
  • 6 rides
  • 7 miles avg distance
All
  • 25 rides
  • Last: Oct 14, 2026
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The Bobby Trail Reports

Status:
on Oct 23, 2025
Variable
Avg: 4.13 (1 votes)
Your vote: 0

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      Directions to the-bobby trailhead (43.545653, -90.963036)

      Photos

      4 more »
      mtb
      267 |
      Jun 23, 2019 @ 6:17pm
      Jun 23, 2019
      mtb
      250 |
      Sep 1, 2018 @ 8:38am
      Sep 1, 2018
      report
      mtb
      59 |
      Oct 23, 2025 @ 7:14pm
      Oct 23, 2025
      report
      mtb
      37 |
      Oct 23, 2025 @ 7:14pm
      Oct 23, 2025

      Videos

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

      Routes with this trail

      ★ 5.0 • 13 miles • 1,398 ft • 14 •
      This Short Course covers pert near ALL of the single track at Sidie Hollow County Park including a trip...
      11 miles • 1,164 ft • 26 •
      The 2019 pertNear 20 has 2 fun routes this year: the Short Course and the Long Course. This Short Course...
      21 miles • 1,997 ft • 42 •
      Featuring all of the best trails that Vernon County has to offer, the pertnear 20 has become one of the...
      5.0 ★★★★★
      1 Ratings
      5 ★ 100%
      4 ★
      3 ★
      2 ★
      1 ★

      1 Review & Comments

      trusstruss
      See comment for this trail accidentally placed on Windup. Trailforks really needs an edit/delete button.

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      • By feardabeastTF Pro TRAILFORKS & contributors
      • #84185 - 2,232 views

      Frequently Asked Questions

      ▼ Where is The Bobby located?
      The Bobby is located in Sidie Hollow Park, Viroqua, Wisconsin, United States. It is part of the Sidie Hollow Park trail network. The trailhead is located at coordinates 43.54565, -90.96304.
      ▼ How hard is The Bobby?
      The Bobby is rated as Blue difficulty. The average grade is 0.001%.
      ▼ What is the elevation gain for The Bobby?
      The Bobby has 373 ft of elevation gain. The trail has 372 ft of elevation descent. The elevation ranges from 1,191 ft to 1,267 ft.
      ▼ Is The Bobby a point to point trail?
      The Bobby is not a point to point trail. The direction is Both Directions. The trail type is singletrack.
      ▼ How long is The Bobby?
      The Bobby is 2.0 miles long. The trail type is singletrack.
      ▼ Are dogs allowed on The Bobby?
      Yes, dogs are allowed on The Bobby. Please keep dogs on a leash where required and clean up after them.
      ▼ How do I access The Bobby? Where is the closest parking trailhead?
      The closest parking and trailhead locations to The Bobby are: View all parking locations in the area.
      ▼ How long does it take to ride The Bobby?
      Based on recorded activities, it takes an average of 13 minutes to ride The Bobby. The trail is 2.0 miles long. Actual times will vary based on fitness level, conditions, and pace. View recent activity logs for more details.
      ▼ How busy is The Bobby?
      The Bobby is a moderately popular trail. There have been 318 recorded activities on this trail. The trail has received 420 check-ins. View recent activity on this trail.

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