Isle of Wight Walking Festival   holiday cottages

Isle of Wight Walking Festival

Laura Kerslake 26 September 2023

Bi-annually, the Isle of Wight sees residents and visitors lace up their hiking boots to explore the island's variety of landscapes, by joining in on one of the many walks that form the Isle of Wight Walking Festival.  

The Isle of Wight Area of Outstanding Natural Beauty covers more than half of the island, so whether you want a short amble or a long hike, there will be a walking trail for you. There are over 50 walks available to choose from during the Isle of Wight Walking Festival. Each of the walks is led by local volunteers who are keen to show you the stunning great outdoors and thriving wildlife that can be found right the way across the island.  

If you are hoping to attend the Isle of Wight’s Autumn Walking Festivals then you'll need somewhere cosy to rest your head at the end of the day. At Island Cottage Holidays, we have a huge range of properties to suit all needs. From dog-friendly cottages to holiday accommodation with hot tubs (perfect for resting those tired legs), we have the perfect home-from-home for you in our collection.  

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When is the Isle of Wight Walking Festival 2023/2024? 

A photograph showing a group of ladies hiking along a path. They are dressed in winter clothes and waterproofs and some are carrying walking poles. In the background, you see some autumnal-looking trees.Copyright: www.visitisleofwight.co.uk 

The Isle of Wight Autumn Walking Festival will take place between 7 and 15 of October 2023, whilst the Isle of Wight Spring Walking Festival will be returning on 11 May until 19 May 2024 to celebrate its 25th anniversary!  

History of the Isle of Wight Walking Festival  

Established back in 1999, the Isle of Wight Walking Festival is now one of the UK's longest-running (and largest) walking festivals. Originally set up by the Isle of Wight Council, the festival is now operated by Visit Isle of Wight and continues to grow year on year. The Spring Isle of Wight Walking Festival takes place annually in May and the Autumn Walking Festival in October.  

Each of the routes is run by knowledgeable volunteer walk leaders, many of whom belong to local ramblers' groups; they know the island, its history, wildlife, coast, and country like the backs of their hands.  

Over the years, the walking festival has provided a vast range of walks suitable for all, from a half-marathon route to historic hikes exploring the island's rich heritage, and walks that explore the Isle of Wight's many beaches. There has even been a speed dating walk that has led to some participants getting married and starting families. 

Isle of Wight Autumn Walking Festival 2023 

A photograph taken from behind showing a couple holding hands. They are walking down a hill towards the beach. 

The autumn event returns on the 7 October 2023 with 55 walks. Each trail covers the coast and/or country, and there is something for every kind of walker, from strollers who like to walk along a sandy beach to curious explorers and hikers alike.  

The Isle of Wight Walking Festival is an inclusive event providing a range of walks suitable for those with reduced mobility, those with pushchairs, or those who prefer a short stroll as opposed to a long hike. You can find the walk grades and facilities key here.  

Festival Favourites  

With such a large variety of walks, it can be hard to choose, so we've rounded up some of our favourites here. From family-friendly strolls to seaside rambles, we're sure you'll find something to suit your group.

Historical Hikes  

A photograph of Osborne House. It is a grand looking home in the middle of fields.

Queen Victoria's Historical Visitors - 7 October

Queen Victoria’s beloved home on the Isle of Wight, Osborne House, is the starting point for this gentle 1.5-mile walk. During her 50 years of staying at the royal holiday home designed by her husband, the monarch welcomed a great many visitors. And it is these famous, and not-so-famous, guests who are the subject of this trail. Follow the route they took to visit the island’s regal residents. 

Distance: 1.5 miles | Difficulty: Easy  

Origin point: At the vehicle entrance to Osborne House, at the top of York Ave, PO32 6JT

Stay nearby: Mast View | sleeps 4  

The Dickens Trail Around Bonchurch - 8 October  

A pencil black and white drawing of famed author Charles Dickens. He is sat at a desk and has a thoughtful look on his face.

For literary lovers, this walk is a must! Classed as fairly easy, this 4-mile walk is led by Sue, one of the friendly festival hosts. Discover all about Dickens' visit to Bonchurch, how it led to the introduction of several important new characters in his masterpiece David Copperfield, and the guests that joined him during his stay.  

Distance: 4 miles | Difficulty: Fairly easy

Origin point: The Pond in Bonchurch, PO38 1RG

Stay nearby: Rose Cottage | sleeps 6  

Guided Walk around Ryde Cemetery - 14 October  

In the largest town of the Isle of Wight, you’ll find Ryde Cemetery, the site for this moderate 1-mile walk. Over the last 20 years, the Ryde Social Heritage Group have been researching and documenting the history and development of the town, the people who lived there and how they lived and died. This information will be shared with you as you tour the three chapels, nine exhibitions and group archives at the cemetery.  

Distance: 1 mile | Difficulty: Fairly easy

Origin point: The Cemetery Gates in West Street, Ryde, PO33 2QF

Stay nearby: The Bolthole – Ryde | sleeps 2  

Seaside Strolls  

A photograph of of four people hiking along the seafront promenade. On the left of the picture, you can see beach huts, and on the right the beach.Copyright: www.visitisleofwight.co.uk

Nurdle hunting walk with Planet Aware - 7 October  

Enjoy this gorgeous 1.5-mile walk from Brook to Compton, part of the island's Area of Outstanding Natural Beauty as you learn about nurdles. These tiny pellets are the building block for many plastic products and sadly, trillions of them end up in the sea every single year threatening a variety of marine life. You’ll learn how to hunt for them in the sand and help protect the environment.  

Distance: 1.5 miles | Difficulty: Fairly easy

Origin point: Brook National Trust Car Park, PO30 4HB

Stay nearby: Fort Redoubt - Upper Caponier | sleeps 6  

Sandown Shanklin Exchange - 9 October  

A photograph of Shanklin Beach and promenade. On the left is the sea, the tide is in. On the right, you can see the pavement. In the distance, there are cars and buildings and behind that is the headland and cliffs.

You can get a little dramatic on this 5-mile beach walk from Sandown Pier to reach Shanklin and Shanklin Theatre. Once you've reached your destination, you will enjoy a talk about the theatre before starting your return journey along the cliff path, where you will meet another group doing the walk in reverse and re-enact the meeting in a special way.  

Distance: 5 miles | Difficulty: Moderate

Origin point:  Sandown Pier, PO36 8JX

Stay nearby: Palmerston Grange - Seahorse Cottage | sleeps 6  

Rock Pooling and Fossil Hunting Walk at Fort Victoria - 11 October  

Fun for the whole family, join the 1-mile stroll at Fort Victoria's rocky beach. The ranger will guide you on how to safely explore the rockpools and spot their inhabitants. Amongst the crabs, anemones and small fish you may even spot a starfish. The Isle of Wight is known as the Dinosaur Capital of Britain, and on this walk, the ranger will also help you hunt for fossils. 

Distance: 1 mile | Difficulty: Easy

Origin point: Ranger's Office at Fort Victoria (next to the toilets), PO41 0RR

Family Favourites  

A photograph showing a young boy walking along rocks. He is walking a very small black dog. In the background, there is a bridge.

Nettlecombe Farm Animal Feeding – 8 October  

Animal lovers of all ages will adore this opportunity to experience a day in the life of a farmer as they take part in the morning feeding duties. Meet animals such as emus, alpacas and reindeer on this 1-mile stroll around Nettlecombe Farm.  

Distance: 1 mile | Difficulty: Easy

Origin point: Nettlecombe Farm, PO382AF

Stay nearby: Shiloh Cottage | sleeps 5  

Fort Victoria History Walk - 10 October

This photograph is taken from within the fort. At the centre of the picture is a large canon pointing out through the opening in the wall to sea. In the sea, there is a sail boat.

Suitable for the whole family, you can join the ranger for a stroll around the remains of Fort Victoria to find out all about this fort built in the 1850s. On this short 0.5-mile amble, you will discover all about how it was built to protect the Solent from the threat of attack from the French and why it was made redundant just a short time later.   

Distance: 5 miles | Difficulty: Easy

Origin point: Ranger's Office at Fort Victoria (next to the toilets), PO410RR 

Stay nearby: Westbury Retreat | sleeps 6  

Cats Protection Circular Walk - 14 October  

This gentle 3.5-mile circular walk takes you from the Cats Protection IOW Adoption Centre, down to the canoe lake and Puckpool Park, and back again. Take in the beautiful sea views of the north-east coast on this family-friendly walk.  

Distance: 3.5 miles | Difficulty: Fairly easy

Origin point: Cats Protection IOW Car Park, PO33 1AW  

Stay nearby: Langonnet Cottage | sleeps 8  

Isle of Wight Walking Festival Accommodation  

A photograph of Palmerston Grange - Seahorse Cottage. It's taken from outside and shows the back of the house and an outdoor table laid with plates and glasses.Palmerston Grange - Seahorse Cottage

Whether you are a solo walker or you're planning to take the whole family to the Isle of Wight Walking Festival, we have the perfect holiday cottage for you. Right across the island, we have holiday homes to suit all party sizes and tastes, so wherever you want to be, we can provide a dream home from home to rest your legs between walks!  

Disclaimer: Whilst every effort has been made to ensure the accuracy of the information at the time of writing, please ensure you check carefully before making any decisions based on the contents within this article.

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