more stats
2.6 miles
Distance
160 ft
Climb
-214 ft
Descent
00:20:55
Avg time
-53 ft
Altitude change
5,342 ft
Altitude min
5,446 ft
Altitude max
5,446 ft
Altitude start
5,394 ft
Altitude end
-0.4%
Grade
-12.8%
Grade max
11.2%
Grade min
1 mile
Distance climb
1 mile
Distance down
1,972 ft
Distance flat
00:20:55
Avg time

Tiddlywinks (Upper) Details

  • Activities
    • Mountain Bike
    • E-Bike
    • Hike
    • Trail Running
  • Riding Area
    Wanoga
    Bend, Oregon
  • Difficulty Rating
    Blue Rate
  • Local Popularity
    95 in Mountain Biking [+]
    • 65 in Trail Running
    • 75 in Hiking
  • Global Ranking
    #26749 in Mountain Biking [+]
    • #1206 in Trail Running
    • #1693 in Hiking
  • Trail Type
    Singletrack
  • Bike Type
    AM, XC
  • Direction
    Both Directions
    Popular In Reverse
  • Climb Difficulty
    Blue
  • Physical Rating
    Moderate
  • Dogs Allowed
    Yes
  • eBike Allowed
    Yes up to Class 1
  • TTFs on Trail
    Rock Garden

This is really a transfer trail from the Wanoga snowpark to what us local refer to as Tiddlywinks. So if you get on this expecting a downhill trail, have no fear, you will get to the goods in about 10-15 min. Trail has a fun start into some rocky bits, then some moderate climbing before you drop into the real tiddlywinks.

Trail Supporters

  • USFS
    Land Manager
Local Trail Association
Traditionally Indigenous Territory

Recent Activity on Trail

Past Week
  • 24 rides
  • 20 miles average
6 Months
  • 222 rides
  • 22 miles avg distance
All
  • 1,648 rides
  • Last: Jul 5, 2026
c1c2c3c4
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Tiddlywinks (Upper) Trail Reports

statusdatedescription
Jun 20, 2026 @ 9:55am (America/Boise)
Jun 20, 2026
Apr 6, 2026 @ 6:45pm (America/Los_Angeles)
Apr 6, 2026
 Absolutely best dirt we'll get. Jumps and berms are perfect
Mar 27, 2026 @ 12:59pm (America/Boise)
Mar 27, 2026
 little snow and mud near the top
Oct 18, 2025 @ 10:28am (America/Boise)
Oct 18, 2025
Jul 22, 2025 @ 3:59pm
Jul 22, 2025
 Bowhead reach goes
more »
Status:
on Jun 20, 2026
Very Dry
Avg: 3.9 (25 votes)
Your vote: 0

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Trail Conditions
  • Unknown
  • Snow Groomed
  • Snow Packed
  • Snow Covered
  • Snow Cover Partial
  • Freeze/thaw Cycle
  • Icy
  • Prevalent Mud
  • Wet
  • Variable
  • Ideal
  • Dry
  • Very Dry
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  • Downhill Primary
  • Both Directions
  • Uphill Primary
  • Uphill Only
  • One Direction
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  • Videos
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Slope Aspect
Direction the slope faces
Flat N NE E SE S SW W NW
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        Directions to tiddlywinks-upper trailhead (43.964190, -121.516520)

        Photos

        18 more »
        93 |
        Jul 6, 2025 @ 9:48pm
        Jul 6, 2025
        140 |
        Jul 11, 2023 @ 7:33am
        Jul 11, 2023
        176 |
        Oct 26, 2021 @ 9:36pm
        Oct 26, 2021
        235 |
        Nov 7, 2018 @ 5:47pm
        Nov 7, 2018

        Videos

        8 more »
        Tiddlywinks / Funner
        6:23 | 108 | Nov 3, 2025 , Bend
        youtuber Tiddlywinks
        8:26 | 356 | Sep 22, 2023 , Bend
        Upper Tiddlywinks tech sections
        160 | Jul 23, 2023 , Bend
        Tiddlywinks Trail - Bend, OR
        11:01 | 633 | Oct 27, 2018 , Bend

        Technical Trail Features (TTF)

        Routes with this trail

        196
        Quick "Best of Wanoga" rip
        ★ 3.6 • 10 miles • 1,239 ft • 17 • Loop •
        Great quick after work ride before it gets dark. Gets the goods of and the DH section without climbing up...
        76
        Tiddlywinks (Upper & Lower)
        ★ 4.5 • 7 miles • 331 ft • 2 • Point to Point •
        151
        Wanoga - Funner to Tiddlywinks
        ★ 5.0 • 13 miles • 1,354 ft • 5 •
        Wanoga - to Tiddlywinks

        Trail Products

        11 Reviews & Comments


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        Frequently Asked Questions About Tiddlywinks (Upper)

        ▼ Where is Tiddlywinks (Upper) located?
        Tiddlywinks (Upper) is located in Wanoga, Bend, Oregon, United States. It is part of the Wanoga trail network. The trailhead is located at coordinates 43.96419, -121.51652.
        ▼ How hard is Tiddlywinks (Upper)?
        Tiddlywinks (Upper) is rated as Blue difficulty. The physical rating is Moderate. The average grade is 0.4%. The climb difficulty is rated Blue.
        ▼ What is the elevation gain for Tiddlywinks (Upper)?
        Tiddlywinks (Upper) has 160 ft of elevation gain. The trail has 214 ft of elevation descent. The elevation ranges from 5,342 ft to 5,446 ft.
        ▼ Is Tiddlywinks (Upper) a point to point trail?
        Tiddlywinks (Upper) is not a point to point trail. The direction is Both Directions. The trail type is singletrack.

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