Planning a visit to the Isle of Wight or just want to soak up some sunshine and good vibes? May is packed with exciting events and activities to help you make the most of the season.
Here’s a round-up of what’s happening across the island:
1. Isle of Wight Challenge (3rd–5th May)
Start the month on a high with this epic endurance event, taking you along the island’s breathtaking coastal paths. Whether you’re walking, jogging, or running, it’s a memorable way to explore the landscape. Find out more.
2. Real Ale Festival (3rd–5th May)
Hosted at the Isle of Wight Steam Railway in Havenstreet, this popular festival celebrates its 20th year! Enjoy a wide range of real ales, ciders, and craft brews with live music and vintage steam trains providing the perfect backdrop.
Free entry | Bar open from 11am–7pm (Sat & Sun), until 5pm on Mon
3. IW Randonnee (4th May)
A much-loved free cycling event inviting riders of all levels to experience the island’s scenic beauty. All they ask is a small donation!
Register here
4. Riverfest (10th May)
Newport’s vibrant quay comes alive with food stalls, live entertainment, music, crafts, and more. A fun-filled family day out with a strong community spirit – and best of all, it’s free to attend.
5. IW Spring Walking Festival (10th–18th May)
Take part in guided walks covering everything from wildlife to local heritage. A brilliant way to explore the Isle of Wight at your own pace.
More info available online.
6. Walk the Wight (11th May)
Join thousands for this beloved annual event, offering routes to suit all ages and fitness levels. Walk, take in the stunning scenery, and support a fantastic cause. Sign up online.
7. Rydabus Weekend (17th–18th May)
A dream for vintage transport fans! Ride classic buses from the 60s–80s and discover the island with charm and nostalgia.
Programme includes route maps, timetables, and exclusive offers. Find out more details here.
8. Festival of Transport (18th May)
Head to the Isle of Wight Steam Railway for a showcase of classic cars, bikes, and machines. A paradise for motoring enthusiasts and a great day out for the whole family. More details here.
9. Cowes Fringe (23rd–24th May)
Cowes bursts into life with this creative festival filled with music, comedy, theatre, and hands-on workshops. Expect quirky venues, vibrant performances, and loads of local talent. Check out the full line-up online.
10. Wild West Week at Blackgang Chine (24th–31st May)
Get your boots on for a Wild West adventure! With themed activities all week long, it’s a hit with kids and grown-up cowboys alike.
Don’t miss the late-night event on Weds 28th – rides after dark, foam party, live DJ, and a firework finale! Tickets available online.