4.5
(603)
7,849
riders
300
rides
Touring cycling routes around Havenstreet And Ashey traverse a landscape characterized by rolling countryside, ancient woodlands like Combley Great Wood, and expansive open chalk downlands such as Ashey Down. The area offers diverse terrains, including routes that follow the heritage steam railway line and provide panoramic views across the Isle of Wight. This region integrates into the broader Isle of Wight cycling infrastructure, featuring varied surfaces and elevations suitable for touring cyclists.
Last updated: April 23, 2026
4.6
(30)
275
riders
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
4.5
(11)
80
riders
24.8km
01:39
310m
310m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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5.0
(1)
27
riders
38.8km
02:34
310m
310m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
14
riders
52.7km
03:23
470m
470m
Hard bike ride. Very good fitness required. You may need to push your bike for some segments of this route.
17
riders
Hard bike ride. Good fitness required. You may need to push your bike for some segments of this route.
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St Mildred’s Church in Whippingham is a Victorian neo-Gothic church closely associated with Queen Victoria and Prince Albert, who worshipped there while living at nearby Osborne House. Rebuilt under Prince Albert’s direction in the 1850s, it features striking architecture, ornate interiors, and a memorial chapel to members of the royal family. Not often open.
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It's not really a shipwreck as such, but it is the remains of the abandoned Paddle Steamer Ryde. See https://en.wikipedia.org/wiki/PS_Ryde
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A great route from city to city. Even children will have no problem riding it🚴♀️🩷😇
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A lovely rural cycleway through woodland and fields which makes for a very pleasant bike ride
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Nice Church with Café - Dogs welcome! We had a lovely afternoon with live music, Tea and cake
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It's got a good scene and wildlife and it's a good trail
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The Sandown to Newport cyclepath is built along the line of a former railway line, and it is the longest cycle path on the Isle of Wight. The route is part of National Cycle Route 23 and passes through some of the nicest countryside the island has to offer.
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There are over 300 touring cycling routes in Havenstreet And Ashey, offering a wide variety of options for different skill levels and preferences. You'll find everything from easy, short rides to more challenging, longer excursions.
The routes in Havenstreet And Ashey feature a diverse landscape, including rolling countryside, ancient woodlands like Combley Great Wood, and expansive open chalk downlands such as Ashey Down. You can expect a mix of surfaces, with some routes following former railway lines for smoother rides, while others might include unpaved segments requiring good fitness.
The touring cycling routes in Havenstreet And Ashey are highly regarded by the komoot community, with an average rating of 4.5 stars from over 600 reviews. Cyclists often praise the varied terrain, scenic views, and the integration with the Isle of Wight's broader cycling infrastructure.
Yes, there are several family-friendly options. The Red Squirrel Trail – Cowes to Newport Cycleway loop from Wootton Bridge is largely traffic-free and suitable for families, leading through ancient woodlands. Many routes also offer sections that are easy and accessible for all skill levels.
Absolutely. For experienced cyclists seeking a challenge, routes like the Newport Quay – Tunnel in Newport loop from Wootton Bridge offer significant elevation gains and longer distances, providing a more demanding ride through varied landscapes.
Many routes offer glimpses of the heritage steam railway line. You can also cycle past the Isle of Wight Steam Railway Museum, explore crafts at Arreton Barns, or visit the prominent Ashey Sea Mark on Ashey Down, which offers panoramic views.
Yes, Ashey Down itself offers panoramic views across the island, and the Ashey Sea Mark is a popular destination for its vistas. Many routes traversing the downlands provide excellent opportunities for scenic overlooks.
Yes, many of the touring cycling routes in the area are designed as loops, allowing you to start and end at the same point. For example, the Sandown to Newport Cycle Path – Pedallers Café, Isle of Wight loop from Wootton Bridge is a popular circular option.
While many outdoor areas on the Isle of Wight are dog-friendly, it's always best to check specific route details or local signage regarding dogs, especially on shared paths or through nature reserves. Generally, dogs on leads are welcome on most public bridleways and cycle paths.
Parking is available at various points around Havenstreet and Ashey, often near popular trailheads or attractions like the Isle of Wight Steam Railway. Many routes, such as those starting from Wootton Bridge, also have accessible parking options nearby.
Yes, you'll find opportunities for refreshments along many routes. The Sandown to Newport Cycle Path – Pedallers Café, Isle of Wight loop from Wootton Bridge, for instance, passes by Pedallers Café. The region's villages and towns, including Wootton Bridge and Newport, offer various cafes and pubs for a break.
The Isle of Wight generally offers pleasant cycling conditions from spring through autumn. Spring brings blooming wildflowers, while autumn provides beautiful foliage. Summer is popular but can be busier. Winter cycling is possible, but some paths might be muddy, and weather conditions can be more challenging.


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