4.6
(655)
7,107
hikers
20
hikes
Hikes around Havenstreet and Ashey explore a landscape of rolling countryside on the Isle of Wight. The area is characterized by a mix of ancient woodlands, such as Combley Great Wood, and open chalk downlands like Ashey Down. Many walking routes near Havenstreet Isle of Wight incorporate views of the heritage steam railway line that runs through the parish.
Last updated: July 7, 2026
4.0
(2)
18
hikers
5.76km
01:33
70m
70m
Embark on a moderate hike through the Havenstreet & Kemphill Moor Copse loop, a 3.6-mile (5.8 km) route on the Isle of Wight. This trail guides you through ancient woodlands and open fields, offering a pleasant journey across the rolling countryside. You will gain about 241 feet (74 metres) in elevation, and it typically takes around 1 hour and 32 minutes to complete. Keep an eye out for views of the heritage steam railway line as you pass through areas like Kemphill Moor Copse, which adds a unique charm to your walk. The path itself is a mix of unpaved and paved sections, with most of it being unpaved.
This moderate hike is suitable for most fitness levels, with generally accessible paths that require some sure-footedness. The starting point for the route is conveniently located near a parking lot, making access straightforward. After your hike, you can explore the nearby village of Havenstreet, which offers amenities such as a beautiful old church, a rural farm, and a local pub, The White Hart Inn. This trail is a good option if you are looking for a hike up to two hours.
What makes this loop notable is its blend of natural beauty and a touch of historical charm. The area is characterized by ancient woodlands and open chalk downlands, providing a tranquil escape. The potential to see the heritage steam railway is a unique element that sets this hike apart. The wider network of footpaths in the Havenstreet and Ashey area is highly rated by the community, indicating a generally positive hiking experience in the region.
5.0
(3)
9
hikers
5.43km
01:27
70m
70m
Step onto The Isle of Wight Steam Railway Museum & Combley Great Wood loop for a moderate hike that takes you through ancient woodlands. You'll wander among old trees, ferns, and moss-covered trunks, creating a magical atmosphere. This route covers 3.4 miles (5.4 km) with an elevation gain of 214 feet (65 metres), and you can expect to complete it in about 1 hour and 27 minutes.
When planning your visit, be aware that conditions can be wet and muddy, especially after rain, so wear appropriate footwear. Some parts of the trail might be uneven or involve uphill sections. You can easily combine your hike with a visit to the Isle of Wight Steam Railway Museum, which is conveniently located near the starting point of the trail.
As you hike through Combley Great Wood, listen for the distant sound of the Isle of Wight Steam Railway, adding a unique auditory element to your walk. The woods are home to a variety of plants and animals, including wildflowers and a chance to spot red squirrels, making it a great spot for nature observation.

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1
hikers
5.13km
01:26
100m
100m
This easy 3.2-mile (5.1 km) loop from Ashley Station offers panoramic views across East Wight and the Solent, with a chance to see steam tra
4.0
(1)
14
hikers
2.26km
00:36
20m
20m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.
4.0
(1)
10
hikers
Moderate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.
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The Isle of Wight Steam Railway is a heritage railway on the Isle of Wight. The railway passes through 5+1⁄2 miles (9 km) of countryside from Smallbrook Junction to Wootton station, passing through the small village of Havenstreet, where the line has a station, headquarters, a depot and a Train Story Discovery Centre. At Smallbrook Junction, the steam railway connects with the Island Line. P.S. You can save some money by buying tickets online.
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Some steps are overgrown with moss and easily missed. In other places the stiles have rotted away, necessitating climbs over fences
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This place gives off some spooky vibes, even on a sunny day you can’t really peer through into the woods beyond first row of the trees. Ferns, moss covered tree trunks and truly magical atmosphere.
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Incredible views await on Ashey Down by the sea mark. As a navigation aid for seafarers it is unsurprising that from here you can enjoy commanding vistas across the Solent to the mainland and to the south across the cliffs and out to sea.
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A good run becomes wonderful if you can time it with the passing of a steam train. The evocative sounds and smells of the engines drift past as you run on by.
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The Isle of Wight Steam Railway Museum is a family-friendly attraction where visitors can discover an extensive collection of beautifully restored steam trains, carriages, and other railway artefacts. The museum also has a number of cafés where you can grab a bite to eat before or after your walk.
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Combley Great Wood is an enchanting woodland located in the heart of the Isle of Wight. The woods feature a diverse range of flora and fauna, including ancient trees and wildflowers, making it an idyllic place for a stroll.
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Havenstreet is a charming little village in the Isle of Wight. It features a beautiful old church, rural farm, and local pub, The White Hart Inn. The village is known for its rich railway heritage, and a few hundred metres south of the village centre is the Isle of Wight Steam Railway museum, which offers visitors a window into the area's rich past.
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Yes, many trails in the area are designed as loops that start and end near a pub. The White Hart Inn in Havenstreet is a popular spot for walkers to get refreshments. You can plan a circular route that passes through the village to finish your hike there.
The woodlands and open downlands are great for walking with dogs. A particularly good option is the loop through Combley Great Wood, which offers plenty of space for dogs to explore. Always be mindful of livestock on downland paths and keep your dog on a lead where required.
Yes, the area is accessible by bus. Southern Vectis bus route 9 stops near Havenstreet, providing access to several trailheads. You can also take a bus to nearby villages like Arreton or Newchurch and start your walk from there. It's a good idea to check the latest timetables before you travel.
The area offers several gentle walks suitable for families. Firestone Copse has accessible trails, some of which are suitable for buggies. For a walk with a unique twist, the Ashley Down loop from Ashley Station is an easy 5 km route that offers the chance to see the steam trains.
For the most impressive panoramic views, head to Ashey Down. The climb to the summit and the historic Ashey Sea Mark rewards you with sweeping vistas across the eastern Isle of Wight and over the Solent towards Portsmouth. Many trails incorporate this high point.
Many footpaths in the area run near or alongside the Isle of Wight Steam Railway, offering great views of the trains. You can start or end hikes at the beautifully restored stations in Havenstreet or Ashey. This allows you to combine a walk with a heritage train ride for a memorable day out.
The trails are highly regarded by the komoot community, with an average rating of 4.7 stars. Hikers often praise the beautiful mix of quiet ancient woodlands and the stunning open views from the chalk downlands. The unique experience of seeing the steam trains is also a frequent highlight.
While there isn't a large dedicated car park right on Ashey Down, walkers often find parking in nearby villages like Arreton or Newchurch and walk up to the down. Alternatively, you can park at Brading Down Viewpoint car park and incorporate Ashey Down into a longer hike from there.
The Ashey Sea Mark is a prominent white pillar on Ashey Down that has been used as a navigational aid for ships for centuries. It's a key landmark in the area, and many walking routes lead directly to it, making it a popular destination for a hike with a historical point of interest.
Yes, for a good moderate hike through the woods, consider the Havenstreet & Kemphill Moor Copse loop. This 5.8 km trail takes you through a mix of peaceful woodland and open fields, offering a varied and engaging walking experience.
There are over 20 designated hiking routes to explore around Havenstreet and Ashey. These range from short, easy strolls to more challenging moderate hikes, covering the area's diverse landscape of woodlands, downlands, and railway paths.


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