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

Bear Photography Workshops

Wildheart Animal Sanctuary

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Sandown
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4 April - 19 September 2026
Join the Wildheart Animal Sanctuary’s new Bear Photography Workshops – a half-day experience perfect for beginners, keen amateurs, or anyone with a passion for nature. Using either a DSLR or just your mobile phone, you’ll enjoy exclusive, safely sectioned access to photograph the resident bears from unique vantage points. With expert tuition from professional wildlife photographer KJ Dudley, you’ll learn simple techniques to capture expressive, dynamic images while building confidence behind the camera. Dates Available:
Bear Photography Workshops at the Wildheart Animal Sanctuary, Sandown
Isle of Wight Festival of Running
Islandwide
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31 May - 7 June 2026
Runners of all abilities will find a course suited to them at The Isle of Wight Festival of Running. From a youngsters’ fun run to the most demanding course, experience the local picturesque scenery and beautiful landscapes via cross-country routes, including the Tapnell 10k and Needles Half-Marathon.
Isle of Wight - Isle of Wight Festival of Running
Cowes Classics Week
Cowes
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4 - 7 June 2026
Come to Cowes and experience Classics Week, focusing on traditional yachts and celebrating with fantastic social events ashore. All types and models of traditional crafts are welcome to negotiate a wide range of Solent courses. The week features daily prize-giving events, furnished with complimentary tea and cake, alongside a special gala awards ceremony for the yacht sailors and crew.
Practical Magic Weekend Retreat

Tiny Homes Holidays

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Cowes
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5 - 8 June 2026
Step away from the noise of everyday life and immerse yourself in a soulful weekend of rest, reflection and renewal at the beautiful eco-retreat, Tiny Homes Holidays. Hosted by Island-born coach and author Kate Taylor, this intimate retreat blends gentle yoga-inspired movement, breathwork, forest bathing, wild swimming, rest and relaxation to help you reconnect with your direction, confidence and inner spark. Nestled beside ancient woodland and just a short distance from the coast, the architect-designed tiny homes offer a peaceful sanctuary where you can slow down, reset and rediscover what truly matters. Expect nourishing food in the beautiful wildflower meadow,...
Practical Magic Weekend Retreat 2026 at Tiny Homes Holidays
The Wight Land Rover Camp Out

Retro Staycations

,
Ryde
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5 - 7 June 2026
The Wight Land Rover Camp Out is a brand new, relaxed and family-friendly campout that welcomes all 4×4 vehicles with rooftop tents/trailer tents, not just Land Rovers. Whether you’re travelling with a fully built overland rig or simply enjoy camping alongside like-minded adventurers, the weekend promises a friendly atmosphere, great conversation and plenty of opportunity to unwind in a stunning setting. There will be a range of hot food offerings on-site for breakfast and dinner, plus a hot and cold drink selection. Families are warmly welcomed, with the Football Fun Factory on hand to keep younger campers entertained.
Isle of Wight Sheepdog Trials
Havenstreet
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6 - 7 June 2026
Following the success of last year’s trials, the Isle of Wight Sheepdog Trials are returning to Rowlands Farm in Havenstreet. Entry to the site is free, but donations will be collected for The Earl Mountbatten Hospice.
Isle of Wight Sheepdog Trials
Portsmouth Pride
Portsmouth & Southsea
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6 June 2026
Celebrating 10 years, Portsmouth Pride is passionate about making the city one of the most inclusive and diverse locations for members of the LGBTQ+ community to live, work or study. The main day Pride event is held every summer and is open to all ages, just a stone’s throw from Southsea Seafront. Enjoy spectacular, carnival-style parades, live music, DJs and entertainment of all kinds!
Rock the Boat
Seaview & St Helens
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13 June 2026
Enjoy an evening of live music, food and fun at Rock the Boat on Saturday, 13th June 2026 at Duver Marina, St Helens, in support of the Sophie Rolf Trust, KissyPuppy. The event features popular Island bands Capital G and The Lazerhearts, with music from 6pm, creating a lively seaside atmosphere for visitors of all ages. Guests can savour delicious food from the Duver Cafe and drinks from Steve’s Bar, all available on-site. The Harbour Water Taxi provides convenient transport to and from multiple points around Bembridge Harbour.
Rock the Boat, St Helens