What’s On Guide

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

Isle of Wight Autumn Walking Festival
Islandwide
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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.
Isle of Wight Literary Festival

Northwood House & Park

,
Cowes
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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
Isle of Wight Literary Festival
Wightrider

Isle of Wight Bus & Coach Museum

,
Ryde
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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.
Wightrider
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.
Beer & Steam

Isle of Wight Steam Railway

,
Havenstreet
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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
Oktoberfest at Powder Monkey Brewing Co
Gosport
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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.
Powder Monkey Brewing Co.
Island Women: Celebrating the Amazing and Inspirational Women of the Isle of Wight

Island Sailing Club

,
Cowes
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14 October 2026
Join Island Women for its fourth ‘In Conversation’ evening, taking place at the Island Sailing Club in Cowes on Wednesday 14th October 2026 at 19:00. Tickets cost £9.50, with money raised going to local charities. The evening celebrates the amazing and inspirational women of the Isle of Wight and is open to all. October’s Guests: Founded by Cheryl Buggy, Island Women celebrates the stories of women across the Island, with event proceeds going to local charities. Tickets cost £9.50 and can be booked through the Island Sailing Club website or by calling 01983 296621. Cheryl also hosts the Island Women...
Island Women event logo against a blue sky background, celebrating inspirational women of the Isle of Wight.
Great South Run
Portsmouth & Southsea
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17 - 18 October 2026
Great South Run, the South Coast’s biggest and best running event, takes place in Portsmouth over a fast and flat 10-mile route. The event is part of an incredible weekend of running that also includes the 5k and Junior Mini Great South Run on Saturday.
Great South Run