more stats
2.0 miles
Distance
373 ft
Climb
-372 ft
Descent
00:11:51
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
00:11:51
Avg time

The Bobby Details

  • Activities
    • Mountain Bike
    • Hike
    • Trail Running
  • Riding Area
    Sidie Hollow Park
    Viroqua, Wisconsin
  • Difficulty Rating
    Blue Rate
  • Local Popularity
    50 in Mountain Biking [+]
    • 5 in Trail Running
    • 5 in Hiking
  • Global Ranking
    #110074 in Mountain Biking [+]
    • #236295 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.

Local Trail Association
Traditionally Indigenous Territory

Recent Activity on Trail

Past Week
  • 0 rides
  •  
6 Months
  • 3 rides
  • 7 miles avg distance
All
  • 22 rides
  • Last: Jun 21, 2026
c1c2c3c4
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The Bobby Trail Reports

statusdatedescription
Oct 23, 2025 @ 9:14pm (America/Chicago)
Oct 23, 2025
 Not to bad. Is a little slick with the leafs on the ground but not terrible.
Aug 22, 2025 @ 9:58am
Aug 22, 2025
Nov 22, 2023 @ 8:59am
Nov 22, 2023
Jun 21, 2023 @ 10:24am
Jun 21, 2023
 reporter
May 26, 2023 @ 5:26am
May 26, 2023
more »
Status:
on Oct 23, 2025
Variable
Avg: 4.13 (1 votes)
Your vote: 0

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  • Snow Covered
  • Snow Cover Partial
  • Freeze/thaw Cycle
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  • Prevalent Mud
  • Wet
  • Variable
  • Ideal
  • Dry
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        Directions to the-bobby trailhead (43.545653, -90.963036)

        Photos

        2 more »
        247 |
        Jun 23, 2019 @ 6:17pm
        Jun 23, 2019
        207 |
        Sep 1, 2018 @ 8:38am
        Sep 1, 2018
        34 |
        Oct 23, 2025 @ 7:14pm
        Oct 23, 2025
        30 |
        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

        23
        2022 pertNear 20 Short Route
        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...
        18
        2019 pertNear 20 Short Route
        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...
        23
        2019 pertNear 20 Long Route
        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...

        1 Review & Comments


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        Frequently Asked Questions About The Bobby

        ▼ 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.

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