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Road cycling routes
United Kingdom
England
South East England

Havenstreet And Ashey

The best road cycling routes around Havenstreet And Ashey

4.1

(252)

11,885

riders

231

rides

Road cycling around Havenstreet And Ashey on the Isle of Wight features varied landscapes, including former railway lines, chalk paths, and waterside scenery. The area provides a range of routes, from relatively flat and accessible paths to those with significant elevation changes. Cyclists can find routes that incorporate scenic countryside, challenging hill climbs, and picturesque loops around waterways. The terrain includes both paved roads and sections that may require good fitness.

Best road cycling routes around Havenstreet And Ashey

  • The…

Last updated: July 10, 2026

3.5

(6)

148

riders

#1.

Bembridge Harbour – Bembridge Windmill loop from Ryde St John's Road

51.6km

02:49

420m

420m

Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.

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Moderate

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

Moderate
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Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.

Easy

Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.

Easy

Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.

Moderate
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Tips from the Community

James
October 1, 2025, Sage Cafe

Fantastic little cafe, great cakes and food and lovely coffee.

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Paul
July 24, 2025, Ryde Hoverport

Fast and fun

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Michael
October 11, 2024, Lagom Coffee Co

Great coffee spot with Scandinavian vibes

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I regularly ride around the Isle of Wight once a year, and can recommend both the Military Road and the inland route taken by the "blue and white flags". In the warmer months of the year (April to October), I would suggest going on a weekday, when there is less holiday traffic.

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These old windmills are the best proof that people were clever enough a number of centuries ago - long before the discovery of electricity and the inventions that resulted from it - to harness the power of the elements for their own purposes: no human or animal muscle power is required for the grinding process, but the wind captured by the wings is enough to drive the heavy millstones and thus, for example, to grind flour from grain (grain mills) or to press oil from olives (oil mills). Unfortunately, they are often only technical and historical evidence of a long tradition of craftsmanship, because most of the old mills have been abandoned over time.

Translated by Google

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Nowadays, only a few of them are still in operation in their original function, but are often just technical-historical monuments to a long tradition of craftsmanship: the heavy millstones inside were moved using the power of the wind as the driving force, for example to grind grain into flour (so-called grain mills) or to press oil from fruits (e.g. olives) (so-called oil mills). These old windmills are therefore the best proof that people were clever enough to harness the power of the wind a number of centuries ago - long before the discovery of electricity and the inventions that followed.

Translated by Google

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The Grade II listed Yarborough monument was erected in 1849 by public subscription in memory of Charles Anderson Pelham, 2nd Earl of Yarborough. After his sudden death in 1846, the committee of the Squadron proposed a ‘Nautical Monument’ or ‘Sea Mark’ in his memory and contributed £200 towards the cost – the Yarborough Monument was the result. This was originally been erected further to the west on top of the Bembridge Down but was moved to its current position in 1867 to make way for the Bembridge Down Fort There's a cafe across the road with seating - hot and cold drinks, cakes and snacks plus The Culver Haven Inn

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Grab a drink and great meal. Sit outside and enjoy the views over the Solent.

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Frequently Asked Questions

How many road cycling routes are available in Havenstreet And Ashey?

There are over 230 road cycling routes around Havenstreet And Ashey, offering a wide variety of options for different skill levels and preferences. The komoot community has explored these routes over 11,000 times.

What is the terrain like for road cycling in Havenstreet And Ashey?

The terrain for road cycling in Havenstreet And Ashey is quite varied. You'll find routes that follow former railway lines, offering relatively flat and accessible paths. Other routes incorporate scenic country lanes, challenging hill climbs, and picturesque loops around waterways like Wootton Creek and the River Medina. While many routes are paved, some sections may require good fitness due to elevation changes.

Are there road cycling routes suitable for beginners or families?

Yes, Havenstreet And Ashey offers routes suitable for various fitness levels, including easier options. For example, the View of the Solent Forts – Appley Tower loop from Ryde St John's Road is rated as easy. Routes along former railway lines, such as parts of the Sandown to Newport Cycle Path, also provide a more accessible experience through pleasant rural landscapes.

What kind of natural features or landmarks can I expect to see on a road cycling tour?

Road cycling routes in the area often feature diverse natural beauty and landmarks. You might cycle past the picturesque Wootton Creek and River Medina, or enjoy panoramic views from areas like St. Georges Down and Arreton Downs. Notable landmarks include the Yarborough Monument and the historic Isle of Wight Steam Railway at Havenstreet Station.

Are there any circular road cycling routes in the area?

Yes, many of the road cycling routes around Havenstreet And Ashey are designed as loops, allowing you to start and finish in the same location. Examples include the Bembridge Harbour – Quarr Abbey loop from Ryde St John's Road and the Yarborough Monument – Bembridge Harbour loop from Ryde St John's Road.

Can I visit the Isle of Wight Steam Railway while on a cycling route?

Absolutely. The Isle of Wight Steam Railway's Havenstreet Station is located within Havenstreet itself, making it a unique attraction that cyclists can easily pass by or incorporate into their ride. It adds a historical and scenic element to your cycling experience.

What do other road cyclists enjoy most about cycling in Havenstreet And Ashey?

The area is highly rated by the komoot community, with an average score of 4.1 stars from over 230 reviews. Cyclists often praise the varied landscapes, which include former railway lines, chalk paths, and waterside scenery, as well as the options for both easy rides and more challenging ascents.

Are there specific routes that follow former railway lines?

Yes, a significant feature of road cycling in this region is the use of former railway lines. The Sandown to Newport Cycle Path, for instance, is built along a former railway line, providing a relatively flat and accessible route through pleasant rural landscapes. This path forms part of National Cycle Route 23.

What are the parking options for road cyclists in Havenstreet and Ashey?

While specific parking facilities for cyclists aren't detailed, Havenstreet and Ashey, being part of the Isle of Wight, generally offer various public parking areas in villages and near popular attractions. It's advisable to check local signage for parking availability and restrictions, especially if you plan to start your ride from a specific point.

Is public transport available for cyclists in Havenstreet and Ashey?

The Isle of Wight has a public transport network, including bus services, which can often accommodate bicycles, though restrictions may apply during peak times or for larger groups. For detailed information on bringing bikes on public transport, it's best to consult the local transport provider's website or the Isle of Wight cycling guide.

Are there any challenging road cycling routes for experienced riders?

Yes, for experienced riders seeking a challenge, the area offers routes with significant elevation changes and demanding ascents. Areas like St. Georges Down and Arreton Downs provide challenging climbs with rewarding panoramic views. The Bembridge Harbour – Undercliff Car-Free Road loop from Ryde St John's Road, for example, features over 800m of elevation gain.

What is the best time of year to go road cycling in Havenstreet And Ashey?

The Isle of Wight generally offers pleasant cycling conditions for much of the year. Spring and autumn provide milder temperatures and beautiful scenery, while summer is popular but can be busier. Winter can be suitable for cycling, though weather conditions may be more unpredictable. Always check the local weather forecast before heading out.

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