Isle of Wight Walking Festival

With more than 70 walks taking place across nine days, the Isle of Wight Spring Walking Festival gives you plenty of ways to explore the Island, whether you fancy a short guided stroll, a heritage walk through town or a demanding day-long challenge. The programme is designed to suit a wide range of abilities, with gentle, moderate and more strenuous routes all included.

Gentle and easy-going walks

If you’d prefer to take things at a relaxed pace, there are several shorter walks that focus on scenery, stories and time to look around rather than covering long distances:

• Queen Victoria’s Island Visitors – 10 May

1.5 miles. Listed as an easy walk with mainly flat walking and good surfaces, making it a good option for anyone looking for a lighter route.

• Hidden Gems of Ryde – 13 May

2 miles. A gentle, easy walk that should suit people who want something short and accessible.

• Pan Together wellbeing Walk – 12 May

2 miles. Also graded easy, with mainly flat walking on good surfaces.

These kinds of walks are ideal if you want to enjoy the festival atmosphere without committing to a long hike.

Moderate walks with a bit more variety

For walkers who want to spend longer out on the trail, the programme also includes routes with a little more distance, changing terrain and some steeper sections:

• Walk the line: Cowes to Newport – 10 May

5 miles. Discover the history of the Cowes to Newport railway at a moderate pace.

• Jacob’s Ladder and St Boniface – 12 May

6 miles. Graded moderate. Encompassing ancient Bonchurch, Jacob’s Ladder & St Boniface Down, the Island’s highest point where WW2 history is evident.

• Two Saintly Lighthouses – 15 May 

7 miles. Another moderate walk with more challenging slopes along the way. After ascending to St Catherine’s Oratory you’ll progress to a hidden cove for packed lunch before visiting St Catherine’s Lighthouse.

• Pier to Pire – To the West – 13 May 

8.1 miles. A longer moderate route with changing scenery and more demanding sections. From Totland Pier to Yarmouth pier via the coastal path with views of the Solent and Hurst Castle, return via Freshwater Causeway.

These walks are a good fit for people who want to see more of the Island and don’t mind a route that asks a little more of them.

More demanding options

If you’re after a real challenge, the festival programme includes walks that go well beyond a casual ramble:

• 24 hour Isle of Wight Coast Path Walk – 9 May

A non-stop 72 mile lap of the Isle of Wight in 24 hours. A challenging brisk walk along the Island’s coastal path, starting at West Cowes Floating Bridge and finishing at East Cowes Floating Bridge.

This is the sort of route that will appeal to experienced walkers looking for a serious endurance challenge.

Walks with a theme

One of the nicest things about the festival is that it is not only about mileage. Some walks are built around a particular subject or experience, giving you a different way to discover the Island:

• A Gentle Stroll Through History in Northwood Cemetery – 11 May

1 mile. A shorter route with a history angle. A gentle walk through history from Victorian times to the present day, hearing about noteworthy people of the town.

• Cowes and East Cowes Maritime History: A Ropey Tale – 12 May

3 miles. Learn about Cowes & East Cowes’ salty past as you walk the town centres looking for historical maritime treasure.

• The Lost Crypt History Walk – 12 May

2 miles, graded easy, and ideal for visitors who enjoy heritage-led experiences. A gentle stroll led by a costumed guide. You will visit sites connected to the founding families of Ryde and other famous characters.

• Seaside Story Walk – 10 May

1.5 miles, with a gentle pace and a fairly easy grade, including plenty of stops for stories, and to find beach treasure, with storyteller Sue Bailey.

• Mottistone and The Longstone – 16 May

3.5 miles, at a gentle pace and graded fairly easy. Walk through an ancient landscape under the custodianship of the National Trust, to view the mysterious Longstone.

This mix of heritage, wellbeing and creative walks is part of what makes the festival feel so varied and welcoming.

Firstly, and most importantly, you can save 20% on foot, car and motorcycle ferry fares to the Island for the Isle of Wight Spring Walking Festival, between 8 and 18 May 2026.

If you’re looking to travel on foot, the best way to get there is on our Portsmouth to Ryde route, which can get you across the Solent in just 22 minutes. Ryde has plenty of efficient connections to the rest of the Island if your walk is starting further inland.

Bus services on the Isle of Wight are operated by Southern Vectis and the Isle of Wight Walking Festival have added the relevant bus route number on each walk on their website.

Our mainland ports each have excellent railway connections, so travelling to and from the Isle of Wight by train couldn’t be easier.

Alternatively, if you would like the comfort of your car pre and post walk, both our Portsmouth to Fishbourne and our Lymington to Yarmouth routes can take you to and from the Island with ease.

Pets are welcome on board if you’re bringing your companion along for the walking fun!

Simply book using the button below to receive your discount.