4.7
(69)
2,856
riders
65
rides
Road cycling routes around Bainbridge are characterized by a hilly topography, offering significant elevation changes across diverse landscapes. The region features a mix of evergreen forests, rolling farmlands, and rocky shorelines. Many routes provide views of Puget Sound, the Seattle skyline, and the Olympic and Cascade Mountain ranges. This varied terrain ensures engaging rides for different skill levels.
Last updated: June 29, 2026
4.7
(7)
258
riders
57.8km
03:17
1,150m
1,150m
Embark on a challenging road cycling adventure with the Wensleydale & Swaledale loop from Bainbridge. This difficult route covers 35.9 miles (57.8 km) and features a significant elevation gain of…
5.0
(1)
178
riders
94.2km
04:58
1,730m
1,730m
Hard road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride.

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4.8
(4)
148
riders
35.6km
02:07
760m
760m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
4.7
(3)
37
riders
24.4km
01:25
380m
380m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
5.0
(1)
27
riders
23.9km
01:12
310m
310m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
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It says private on the gate 🤔but then asks you not to climb on the rocks and stick to the path . I went in for a mooch . Lovely garden
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Have a look at the famous Yorkshire Creamery, also known from the Wallace and Gromit movies;) You can watch the cheese making at 10.15am, 12pm, 1pm, 2pm, 3pm and last chance at 3.45pm. Free tasting of different types of cheeses and factory sales of those. Nice, little shop with all types of cowish, sheepish and Yorkshirish devotionals.
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Fantastic loop from Hawes to Muker then Cross tops to Askridge then steady back to Hawes . The climbs are tough but an awesome ride
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This is the summit of the climb from Wensley up past Castle Bolton, steep there and then the long long climb with 14% as the steepest...
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Epic climb with brutal finish before plateauing and taking in the long descent. Headwind was relentless and a battle to stay on the bike at the top. No mean feat getting up there any day. 👍
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Bainbridge Island offers a surprisingly hilly topography despite being at sea level, with routes featuring significant elevation changes. You'll encounter a mix of evergreen forests, rolling farmlands, and rocky shorelines. Some routes provide breathtaking views of Puget Sound, the Seattle skyline, and the Olympic and Cascade Mountain ranges.
Yes, Bainbridge Island is known for its challenging climbs. Hills like Arrow Point Drive, Koura Road, Baker Hill Road, and Toe Jam Hill Road (which boasts a 23% gradient) provide demanding ascents for advanced riders. A 30-mile route on the island can include as much as 3500 feet of climbing.
Many routes offer stunning views of Puget Sound, the Seattle skyline, and the Olympic and Cascade Mountains. You can also experience 'cathedral-like canopies' within evergreen forests, open farmlands, and rocky shorelines. Manitou Beach Open Space, for example, provides views across to Seattle and Mount Rainier.
While many routes feature significant hills, the island also has a network of mostly paved rural and suburban-style lanes, along with dedicated bicycle lanes and mixed-use paths. Flatter options exist along Crystal Springs Road, which can be suitable for families or those seeking a less strenuous ride.
The region is generally pleasant for cycling during the warmer months, typically from spring through early autumn, when the weather is milder and rainfall is less frequent. This allows for the best enjoyment of the scenic views and diverse landscapes.
Parking is available at various points around the island. For instance, Fort Ward Park is a good spot to include in a ride and offers parking. The main town of Winslow is also easily accessible and provides amenities, including potential parking options.
Yes, Bainbridge Island is well-suited for loop routes, allowing cyclists to explore diverse landscapes without retracing their path. The iconic Chilly Hilly Loop, a 33-mile ride, is a prime example, offering rolling hills, forested roads, and shoreline views in a circular format.
You can incorporate various attractions into your rides. The Grand Forest offers immersive forest experiences, while Fort Ward Park provides historic sites and scenic biking. The town of Winslow offers shops, restaurants, and the Bainbridge Island Museum of Art. The Bloedel Reserve, a 150-acre forest and garden, can also be a peaceful stop, though it requires timed tickets.
There are over 60 road cycling routes available around Bainbridge Island, catering to various skill levels. These include 7 easy routes, 37 moderate routes, and 22 difficult routes, ensuring options for everyone from casual riders to experienced cyclists.
The road cycling experience on Bainbridge Island is highly rated by the komoot community, with an average score of 4.7 stars from over 60 reviews. Cyclists frequently praise the varied terrain, from rolling hills and dense forests to stunning shoreline views, and the engaging challenge of the routes.
Yes, bike rentals are available near the ferry terminal, making it convenient for visitors to explore the island on two wheels without bringing their own equipment.
The main town of Winslow is easily accessible by bike and offers a variety of shops and restaurants where you can stop for refreshments. Many routes also pass through or near smaller communities that may have local cafes.


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