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Isle of Wight Themed Walks and Trails (2025 Guide)
The Isle of Wight Coastal Path or a circular coastal route is my go-to suggestion for keen walkers who want to see the best of the Isle of Wight. If I can't see the sea on an Isle of Wight walk, then I feel short-changed.
However, there are plenty of other options that are themed around local history or a particular town. They are sometimes circular and can be completed in a few hours, whereas the coastal path requires several days. Also, some of the coastal path isn't child-friendly because of dangerous drops from cliffs.
We've dug out a few themed walks that are available online for free, mostly from the lovely people at Visit Isle of Wight. Some suggest actual routes whilst others just point out landmarks and leave you to work out how to get from A to B.
We've got a separate guide for families with very short strolls of 1-2 miles. These are good for dragging along children who would rather be sat at home playing Minecraft. There's also a thorough list of trails on the Isle of Wight Council website.
However, there are plenty of other options that are themed around local history or a particular town. They are sometimes circular and can be completed in a few hours, whereas the coastal path requires several days. Also, some of the coastal path isn't child-friendly because of dangerous drops from cliffs.
We've dug out a few themed walks that are available online for free, mostly from the lovely people at Visit Isle of Wight. Some suggest actual routes whilst others just point out landmarks and leave you to work out how to get from A to B.
We've got a separate guide for families with very short strolls of 1-2 miles. These are good for dragging along children who would rather be sat at home playing Minecraft. There's also a thorough list of trails on the Isle of Wight Council website.
Themed Walks about local people (and a horse)
- The Havilland Cottage Dickens Trails are two walks that have been created by the owners of a cottage in Bonchurch. They're based around the time Dickens spent in Bonchurch writing David Copperfield. The two routes are on Google maps and there's more detail about Dickens on the Isle of Wight on their website. I've not done the walks yet, but the creators reckon the short walk is about an hour and the longer walk is about two hours.
The Bonchurch end of the Bonchurch to Ventnor coastal path
- Victoria's Island Trail follows the route that a young Victoria Beckham (nee Adams) took on a school trip to the Isle of Wight in the mid 1980s. Obviously that's not true, but I like to see if anyone is reading this waffle.
It actually came out to coincide with the release of Victoria and Abdul a few years ago. There's a printable document with snippets of history about different pages and there's an itinerary for walkers that takes in some of the highlights. I'm not sure on the exact distance but it's an all-day thing. - A similar alternative is Queen Victoria's Town Trail, which wanders around East Cowes. It was created to coincide with the 200th birthday of Queen Victoria and Prince Albert. Unfortunately, the couple were unable to attend their birthday celebrations.
This church in Whippingham was a popular spot for Queen Victoria
- The Churchill Trail points out the various places on the Isle of Wight with connections to Winston Churchill. They include Winston's holidays in Ventnor and his parents' whirlwind romance in Cowes. There isn't a specific trail, you just plot your own path.
You can actually stay in the house that Churchill's parents met in, as it's now a National Trust holiday home. The two parts of the house are called Rosetta Cottage and East Rosetta Cottage.
I am currently working on The Truss Trail, which will show visitors various Isle of Wight landmarks with links to former Prime Minister, Liz Truss. Current highlights include a visit to a sewage outlet pipe and the remains of a business forced to close due to increased mortgage rates (Ed: sounds fascinating). It will cover 49 metres, one for each of her days in office.
Churchill's parents met and got engaged at this house in Cowes
- The Warrior Trail is a six mile walk around some pretty parts of the West Wight, which celebrates the role of a famous horse. Apparently it's nothing to do with the War Horse film, but it is about a horse during the same war, so I'll forgive your confusion. There's a PDF of the route.
Mottistone Manor features on the Warrior Trail
- The Literary Heroes Trail is more of an iSpy for book worms, as it shows you all the Isle of Wight places with a literary connection rather than planning a whole route for you (as far as I can tell). Tennyson features heavily as he set up home in Freshwater.
Tennyson Down, which was named after a writer (I forget which one)
music themed walks
- The Tapnell Trail is a route around the 1970 Isle of Wight Festival site. It starts from Tapnell Farm that has a relaxed restaurant, which serves up decent burgers. It's about six miles but you can cut off a corner. My mother did this one and said that it was pretty but that the scenery wasn't stunning compared to some Isle of Wight walks.
- Nostalgic old hippies might also enjoy the musical trail around Wootton that covers the site of the 1969 Isle of Wight Festival.
Local history themed walks
- The Rope Walk is a trail that links (West) Cowes and East Cowes and shows off their maritime history. I don't know the exact distance but it says it takes about three hours. It would be about three days with my family by the time we'd stopped at a café and a playground and then given up because we'd run out of snacks for the children.
See our lovely video of a sunny morning in Cowes.
Cowes and East Cowes are the place to go if you like lots of yachts
- The Niton Smugglers' Trail was created by Niton and Whitwell Parish Council. It's a very detailed document about how the most of the village was seemingly involved in the smuggling trade in the 19th century and includes 14 places to stop. The map is on page 17. The smugglers trail is about 4.5 miles.
St Catherine's Lighthouse in the South Wight
- The West Wight Heritage Trail (13 miles) and the Freshwater Bay Heritage Trail (6 miles) were created by a B&B in Freshwater. The longer route is mostly coastal and includes Yarmouth Castle, Fort Victoria and The Needles.
The coastline along the West Wight is a bit tasty
- The Robert Hooke Trail is a 8.5 mile circle around the West Wight, including some really pretty spots around Freshwater Bay and the coastal path at Yarmouth. There are information boards along the route, telling you about Hooke's life. He was a pioneering scientist and also a key figure in rebuilding London after the fire of 1666.
You might like to incorporate a visit to Dimbola, which is a photographic museum in Freshwater Bay or a stop in one of the cafes or pubs in Yarmouth (we like Gossips Café).
One of Robert Hooke's 17th century inventions is still used in your car today (no, it's not the cup holder)
- Ventnor has a series of information boards called Time Travel Ventnor, which can be completed in a circular route. Each one has some blurb about the town's history, including how it grew into a Victorian resort. There's also a small Heritage Centre on route if you really get into it.
A more sarcastic guide to the Isle of Wight might suggest that any visit to Ventnor feels like you are time travelling. Of course, I wouldn't make such cheap gags.
There are nine boards which make up the Time Travel Ventnor trail
- Ryde has a Heritage Audio Trail that was created by the Ryde Social Heritage Group. You walk around the town in a circular-ish route and stop off at 17 locations including Ryde Pier and Ryde Castle. Each stop is accompanied by an audio description that you can listen to on your phone.
I'm not sure on the exact length (Ed: oooeer missus) but the guide suggests it will take a couple of hours. Ryde is quite a hilly town so expect sore thighs.
- There are eight display boards called 'Holy Wells and Pilgrim Paths' that follow a route around the South Wight. We stumbled across board number five at a terrific viewpoint overlooking The Undercliff.
The boards provide some interesting local history about The Undercliff and local Saints but there's nothing about the route online. From what I can tell, they were paid for by an organisation that no longer exists (The Local Heritage Initiative). I'm not exactly sure how long the route is, and there isn't a route map to download. However, it looks about three miles to me. Perhaps we will leave this one to adventurers who won't mind getting lost a few times...
The Holy Wells and Pilgrim Paths trail is made up of eight signs in the South Wight...
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...although this is the best I can offer for a route map (the scale says 300m)
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Pub themed walks on the Isle of Wight
You can stumble your way round 10 historic walks which tour between past-and-present pub locations of the Isle of Wight. They were created for the Beer and Buses weekend.
Options include Carisbrooke, Cowes, Gurnard, Northwood, Newport, Shanklin, Ryde, Shanklin, Ventnor and West Wight. *Hiccup*
Options include Carisbrooke, Cowes, Gurnard, Northwood, Newport, Shanklin, Ryde, Shanklin, Ventnor and West Wight. *Hiccup*
Nature themed walks on the Isle of Wight
The Histree Trails is a series of Isle of Wight walks which show off the Island's most significant and oldest trees. There are eight walks in total with names like 'Poets and Pines Histree Trail'.
Perhaps I'm getting old, but I was surprisingly interested in being told that a tree might be 500 years old or that fishermen used the willows in Yafford to make lobster pots.
They range in distance from about 2-10 miles and have nice maps to reduce the risk of getting lost.
They were written about 15 years ago, so there's a caveat on the website that says 'these trails are no longer accurate, and several of the trees in them are now lost to old age or inaccessible'. Still, you might get to see a collection of lovely old stumps.
Perhaps I'm getting old, but I was surprisingly interested in being told that a tree might be 500 years old or that fishermen used the willows in Yafford to make lobster pots.
They range in distance from about 2-10 miles and have nice maps to reduce the risk of getting lost.
They were written about 15 years ago, so there's a caveat on the website that says 'these trails are no longer accurate, and several of the trees in them are now lost to old age or inaccessible'. Still, you might get to see a collection of lovely old stumps.
River themed walks on the Isle of Wight
An organisation called Island Rivers offers trails with a rivery theme (Ed: stop making up words),
The Yar River Trail is an interesting one, as it follows the entire river from its source to the sea. It starts with a spring in Niton in the South Wight before wiggling its way to Bembridge in the East Wight.
The whole thing is 19 miles so some people split it up.
Another popular river themed walk on the Isle of Wight is the Medina Estuary Trail. It's a circular walk which heads down one side of the River Medina and back up the other. It's about 9 miles.
The Yar River Trail is an interesting one, as it follows the entire river from its source to the sea. It starts with a spring in Niton in the South Wight before wiggling its way to Bembridge in the East Wight.
The whole thing is 19 miles so some people split it up.
Another popular river themed walk on the Isle of Wight is the Medina Estuary Trail. It's a circular walk which heads down one side of the River Medina and back up the other. It's about 9 miles.
The Medina Estuary Trail goes up on side of the river and down the other
