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968 ft
Distance
-16 ft
Descent
00:01:57
Avg time
-16 ft
Altitude change
161 ft
Altitude min
180 ft
Altitude max
179 ft
Altitude start
164 ft
Altitude end
-1.7%
Grade
-7.3%
Grade max
2.2%
Grade min
138 ft
Distance climb
417 ft
Distance down
413 ft
Distance flat
00:01:57
Avg time
Flying Jenny Details
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Activities
- Mountain Bike
- Winter Fat Bike
- Hike
- Trail Running
- Snowshoe
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Riding AreaWoody Hill
Westerly, Rhode Island -
Difficulty Rating
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Local Popularity100 in Mountain Biking [+]
- 90 in Trail Running
- 85 in Hiking
- 5 in Snowshoeing
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Global Ranking
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Trail TypeSingletrack
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Bike TypeAM, XC, Fat
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DirectionDownhill Primary
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Dogs AllowedYes
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eBike Allowed
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Land OwnerWesterly Municipal Land Trust
Flying Jenny was the second trail built and basically became a connector trail from North Main Street to Hobbit Juice. This trail has a few short rock gardens with off-camber turns into rocks for added fun. At the end there is a huge boulder that you can either ride up and take one of three rollers down or simply ride in front of it. The trail orginally continued to a mini-sidewinder, but that section was merged into Captains Daughter.
Brewery: Grey Sail Brewing, Westerly, RI.
Local Trail Association
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Please consider joining or donating to the local trail association to supportDonate to earn trail karma!
trail development & maintenance.
Traditionally Indigenous Territory
Recent Activity on Trail
Past Week
- 14 rides
- 12 miles average
6 Months
- 248 rides
- 11 miles avg distance
All
- 3,780 rides
- Last: Jun 19, 2026
| c1 | c2 | c3 | c4 |
|---|---|---|---|
January | February | March | April |
May | June | July | August |
September | October | November | December |
Flying Jenny Trail Reports
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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
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The colour categories are based on what percentage of riders are riding a trail in its intended direction.
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- > 6 months
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- Downhill Primary
- Both Directions
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- Uphill Only
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Directions to flying-jenny trailhead
(41.380870, -71.737840)
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Routes with this trail
★ 4.0 • 16 miles • 981 ft • 23 •
This is the beginner/relaxed loop for the 2023 Woody Hill Fun Ride
14 miles • 928 ft • 22 •
This is the RINEMBA 2024 Woody Hill Fun Ride Intermediate Loop
★ 2.0 • 22 miles • 1,696 ft • 31 •
This is the expert loop from the 2025 Woody Hill Fun Ride
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Nearby Trails
- South Main Street 315 ft
- Peeptoad 377 ft
- Bud Light 781 ft
- Connector 6 1,066 ft
- West Main Street 1,165 ft
- By butters
& contributors - #117169 - 1,473 views
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Frequently Asked Questions About Flying Jenny
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Where is Flying Jenny located?
Flying Jenny is located in Woody Hill, Westerly, Rhode Island, United States. It is part of the Woody Hill trail network. The trailhead is located at coordinates 41.38087, -71.73784.
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How hard is Flying Jenny?
Flying Jenny is rated as Blue difficulty. The average grade is 1.7%.
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What is the elevation gain for Flying Jenny?
The trail has 16 ft of elevation descent. The elevation ranges from 161 ft to 180 ft.
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Is Flying Jenny a point to point trail?
Flying Jenny is not a point to point trail. The direction is Downhill Primary. The trail type is singletrack.
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