What’s On Guide

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Don’t miss any events during your visit

Our what’s on guide is updated throughout the year, bringing you events to suit all ages and interests across the Isle of Wight. Annual favourites include the Isle of Wight Festival and Cowes Week, the famous Round the Island Yacht Race, Walk the Wight and of course the Garlic Festival.

Every month brings countless opportunities to enjoy live music at venues across the Island, from pubs like The Spyglass Inn to The Wight Proms and Jack Up Events. During the summer months, don’t miss our historic town carnivals and local favourites, such as The Chale Show and the Royal Isle of Wight County Show.

Many of our leading attractions also host special events to keep you entertained, including the Isle of Wight Steam Railway, Blackgang Chine, Robin Hill and The Needles Landmark Attraction.

Our Isle of Wight events guide is always packed with diverse and entertaining activities, so you don’t need to miss a thing.

What's on all year round

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Isle of Wight Autumn Walking Festival

Islandwide

3 - 11 October 2026

The second instalment of the Isle of Wight Walking Festival takes place in October beneath a canopy of fiery, autumnal changing leaves, offering a chance to discover the best of the Island at this special time of year.

Dash in the Dark

Newport

3 October 2026

On your mark, get set, GLOW! Dash in the Dark, the 5K fun run, raising vital funds for the Hampshire and Isle of Wight Air Ambulance, returns to a brand-new location: Robin Hill! Gather your glow gang and get ready to walk, jog, run or dance your way around this special nighttime mission. There will be lights, music and plenty of fun along the way, so grab your fluorescent clothing, glow in the dark paint or bring your glow sticks!

The Wonder of Stevie

Shanklin Theatre

Shanklin

3 October 2026

The ultimate celebration of the genius of Stevie Wonder! Voted one of Britain’s top soul singers, mesmeric vocalist Noel McCalla, award-winning saxophonist Derek Nash (Jools Holland’s R&B Orchestra) and their world-class live band present a diverse catalogue of Stevie Wonder classics from the dance floor classics. ‘I Wish and Superstition’ to the beautiful arrangements of ‘My Cherie Amour’ and ‘I Just Called to Say I Love You’ and the much-loved ‘Isn’t She Lovely’ and ‘Don’t You Worry ’bout a Thing’. The show will also feature compositions by Stevie that other artists have had massive hits with.

Isle of Wight Literary Festival

Northwood House & Park

Cowes

8 - 11 October 2026

The Isle of Wight Literary Festival provides a far-reaching, eclectic programme. Hosted at Northwood House in Cowes over four days, 60+ writers and presenters will share their latest works. Topics include crime fiction, history, travel, maritime adventure, gardening, medicine, technology and the social and political issues of our time

Oktoberfest at Powder Monkey Brewing Co

Gosport

10 October 2026

Celebrate Oktoberfest with Powder Monkey Brewing Co on Saturday 10th October 2026 at the Explosion Museum in Gosport, beside the brewery’s taphouse. Choose from two sessions, 12pm-5pm or 6pm-11pm, and enjoy the brewery’s biggest event of the year, featuring live entertainment, delicious food and a fantastic festival atmosphere. Sample exclusive Powder Monkey beers brewed especially for the occasion, raise a stein and join in the celebrations for a memorable day of Bavarian-inspired fun.

Wightrider

Isle of Wight Bus & Coach Museum

Ryde

10 - 11 October 2026

Organised by the Isle of Wight Bus & Coach Museum, Wightrider allows you to enjoy free classic bus rides to destinations and attractions across the eastern side of the Island over the weekend. Programmes giving full details and a timetable are available to buy online, with proceeds going towards the museum.

Beer & Steam

Isle of Wight Steam Railway

Havenstreet

10 - 11 October 2026

Head to the Isle of Wight Steam Railway’s Autumn beer festival for a celebration of beer and steam. Choose from a huge selection of real ales; there are even a few ciders for those with a sweeter tooth. You’ll have the opportunity to try local brews from Yates’, Goddards and Island Brewery alongside ales from Yorkshire, Somerset and more.

Isle of Wight Steam Railway - Beer & Steam

Notes at Noon - Music for Piano and Winds

Ryde

10 October 2026

Curated by James Longford, Notes at Noon is a new monthly concert series at Garfield Road Methodist Church in Ryde, featuring professional musicians. In the penultimate concert in the Notes at Noon series, join James and some wonderful Island woodwind players for a recital of music for piano and wind ensemble.