4.1
(268)
12,121
riders
218
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.
Last updated: October 27, 2026
3.8
(10)
174
riders
30.9km
01:28
360m
360m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
56
riders
27.4km
01:20
230m
230m
Easy road ride. Mostly well-paved surfaces and easy to ride.

31
riders
20.1km
00:57
170m
170m
Easy road ride. Mostly well-paved surfaces and easy to ride.
5.0
(1)
25
riders
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.
18
riders
60.3km
02:49
640m
640m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
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Classic Isle of Wight scenery: a small hilltop village with thatched roofs, narrow lanes and, atop the slope, the medieval parish church. From the churchyard, you look out over the patchwork fields around Godshill; below lies the compact village ribbon with its photogenic cottages. A short climb, a quiet moment at the top, and then back through the old centre.
2
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A village with almost only thatched houses and again a remarkable church on top of the hill.
1
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I've never seen a post this helpful. I appreciate it and hope to see more postings like this one in the future. Many thanks. https://mymilestoneecard.online/
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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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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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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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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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