22
riders
4
rides
Gravel biking around Winston, Oregon, offers access to diverse terrain within the Umpqua River Valley and the Umpqua National Forest. The region features rolling hills, river valleys, and extensive forest lands, providing a variety of unpaved roads and trails. These landscapes are characterized by a mix of natural surface roads and gravel paths, suitable for gravel cycling. The area's proximity to the Umpqua National Forest ensures numerous opportunities for rides through forested environments.
Last updated: June 29, 2026
3
riders
30.1km
02:34
620m
620m
Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
6
riders
55.7km
03:23
470m
470m
Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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5
riders
36.9km
02:32
580m
580m
Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
1
riders
56.4km
03:59
830m
830m
Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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Hard packed former railway, now a popular walkway for cyclists and walkers. A good route to Bishop Auckland and beyond. Can get busy on weekends.
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Open 10-4 everyday except Tuesday. Great coffee and cake, bacon/sausage butties. Enough bike parking for a group ride, plus a maintenance station with pump and tools. Walkers, runners, kayakers and dogs all welcome!
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Fantastic place to stop for lunch, or coffee and cake. Safe bike-parking round the back. Open 10-4 every day (closed Tuesdays).
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This viaduct was used as a railway for the Tees Valley Railway Company, for which it was built in 1868. Now, out of use, you can cross it on foot.
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There are several gravel biking routes around Winston, offering diverse terrain. Our guide features 6 distinct routes, ranging from moderate to difficult, allowing you to explore the Umpqua River Valley and the Umpqua National Forest.
While many routes in the Winston area are rated moderate to difficult due to elevation changes and varied terrain, beginners can still find suitable sections. For a moderate challenge, consider the Cotherstone Castle – Tees Railway Path loop from Barnard Castle, which offers a good introduction to the region's river valleys and historical areas.
For experienced gravel bikers seeking a challenge, Winston offers several difficult routes. The River Deerness – National Cycle Route loop from Bolam is a demanding 34.6-mile path with significant elevation changes, providing a robust workout through varied landscapes. Another option is the The Old Chapel Café – Tees Railway Path loop from Barnard Castle, which features substantial climbs over its 36.9-mile distance.
Gravel biking around Winston takes you through a variety of scenic landscapes. You'll encounter lush forests, particularly within the Umpqua National Forest, rolling hills of the Umpqua Valley, and picturesque river valleys along the South Umpqua River. Many routes utilize Forest Service roads, offering a true immersion in nature.
Yes, many of the gravel routes around Winston are designed as loops, allowing you to start and end at the same point. An example is the popular Welcome to Richmondshire – The Stang loop from Newsham, which covers 18.7 miles and features significant elevation gain.
Winston benefits from a Mediterranean climate, making it conducive to outdoor activities year-round. However, the spring and fall often offer the most pleasant temperatures for gravel biking, with less heat than summer and generally drier conditions than winter. Always check local weather and trail conditions before heading out.
Beyond the natural beauty, the Winston area has several points of interest. You can explore historical sites like Egglestone Abbey Ruins or Raby Castle. The region also features unique structures such as the Whorlton Suspension Bridge and the historic Winston Bridge.
While many routes venture into natural areas, some pass near small towns or villages where you might find local amenities. For example, the The Old Chapel Café – Tees Railway Path loop from Barnard Castle route name suggests proximity to a café. It's always a good idea to carry sufficient water and snacks, especially on longer rides in remote sections of the Umpqua National Forest.
The gravel biking routes around Winston are highly regarded by the komoot community, with an average rating of 4.5 stars. Riders often praise the diverse terrain, the solitude of the forest roads, and the scenic views offered by the Umpqua River Valley and surrounding hills.
When riding in the Umpqua National Forest, be aware that some gravel roads, like Calf Ridge Road or Bachelor Butte Road, may pass through burned areas. This can mean encountering rocks and debris, so caution is advised. Always be prepared for varying road conditions and potential wildlife encounters.
For general visitor information about Winston and the surrounding region, including other attractions and local services, you can visit the official tourism website for Oregon at visitoregon.com.


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