Events, Festivals and Exhibitions

Isle of Wight Walking Festival 2023

7 October 2023 - 15 October 2023

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The Isle of Wight Walking Festival will take place in October 2023. Walkers of all abilities can join in the two weeks.

With more than half of the Isle of Wight designated as an Area of Outstanding Natural Beauty, 500 miles of well-maintained footpaths and 60 miles of coastline, the island is noted for its great walking.

History of the Isle of Wight Walking Festival

The first festival was held in 1999, consisting of 39 walks.

Most of the guided walks are free, although some leaders may request a donation for charity. This provides you a great opportunity to see the diverse landscapes on offer in the island, as well as to meet colourful locals. You are advised to book ahead.

Isle of Wight Walking Festival
Isle of Wight Walking Festival – credit Visit Isle of

This year’s walking festival programme can be found here.

New for this year is the 5k Dash in the Dark fundraiser for the Hampshire and Isle of Wight Air Ambulance.

Last year’s programme included a tour around the RSPB’s site at Brading Marsh, and a stroll across the Needles Half Marathon route along The Freshwater Way, with views of Compton and Totland Bay, and across Headon Warren, The Needles and Tennyson Down. This is one of our Three Best Isle of Wight Walks.

There is also the Terrace’s Yarmouth River Loop, another of our favourite West Wight walks. Alternatively wander with appropriately named local historian Tim Wander, to Puckpool gun battery and Appley Tower. Or for something a little more scary you can do the Lost Crypt Ryde Walk, with echoes of Jack the Ripper – after all many people have migrated from the Eastend of London to the Isle of Wight.

Registration is available now, and you are recommended to do so swiftly as the walks tend to full up fast.

When is the Isle of Wight Walking Festival 2023?

The 2023 Festival will be held from 7 to 15 October.

For more information on Victoria’s association with the island and walking opportunities on Tennyson Down, read Mark Bibby Jackson’s Isle of Wight Holidays: Walks, Pubs and Victoria.

Headon Warren - credit Visit Isle of Wight dot co dot uk
Headon Warren – credit Visit Isle of

Things to Do on the Isle of Wight

The Isle of Wight has a wonderful history with Carisbroke Castle, where King Charles I was locked up prior to his execution, and Queen Victoria’s beloved Osborne House both run by English Heritage and open to the public. Read more here.

Isle of Wight Festival Season

The Isle of Wight Walking Festival is just one of many festivals on the island. Other festivals include: the Isle of Wight Literary Festival, Ventnor Fringe, Lendy Cowes Week and the Isle of Wight Festival.

Isle of Wight Accommodation

If you are looking for accommodation on the island during your stay, please fill in the form below. It will cost you nothing extra, but the small commission we take helps with the running of this website. alternativels, visit:

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For more information on the Isle of Wight Walking Festival 2023

Click here.

Cover Photo credit Visit Isle of


7 October 2023
15 October 2023


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Mark Bibby Jackson

Mark Bibby Jackson

Before setting up Travel Begins at 40, Mark was the publisher of AsiaLIFE Cambodia and a freelance travel writer. When he is not packing and unpacking his travelling bag, Mark writes novels, including To Cook A Spider and Peppered Justice. He loves walking, eating, tasting beer, isolation and arthouse movies, as well as talking to strangers on planes, buses and trains whenever possible. Most at home when not at home.

Read more posts by Mark Bibby Jackson →

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