The Isle of Wight is bursting with events this May, from scenic walking festivals to live music, local fairs, and vibrant cultural celebrations. Whether you’re a local or visiting the island, here’s your guide to the best things happening this month.
Kick off May with the IOW Ultra Challenge, one of the island’s most exhilarating endurance events. Runners from across the UK tackle scenic routes around the Isle of Wight, enjoying stunning coastal views and the thrill of competition.
For walking lovers, the Spring Walking Festival is a must. From May 9th to 17th, enjoy guided walks, coastal hikes, and countryside strolls showcasing the island’s beautiful landscapes. Perfect for all ages and fitness levels, it’s a fantastic way to explore hidden corners of the Isle of Wight. Make sure to register for your walk through their website.
On May 9th, Riverfest brings the community together for a day of riverside FREE fun, music, and activities. This family-friendly event is ideal for a relaxing day out soaking up the local atmosphere.
Get ready to dance the weekend away at Robin Hill Adventure Park with the Isle of Wight Dance Weekender. Over two days, enjoy live DJ sets and a vibrant mix of house, garage, pop, and high-energy dance tracks – an unmissable event for music lovers visiting the island. You will get to see the likes of Professor Green, Majestic, Gok Wan and Artful Dodger. Get your tickets here.
Also on May 9th, the Wolverton Folk & Blues Fair celebrates traditional music with live performances, workshops, and a chance to meet fellow folk enthusiasts. A highlight for music lovers of all ages.
The iconic Walk the Wight returns on May 10th, offering walkers multiple scenic routes across the island. Whether it’s a challenging trek or a gentle stroll, it’s a wonderful way to enjoy the island’s coastline and countryside. Click here to sign up to Walk the Wight.
Islanders’ favourite is back—and bigger than ever! Step aboard a variety of vintage buses from the 60s, 70s, and 80s as they run on specially themed routes across the island.
Grab a programme from their website to get timetables, route maps, and exclusive offers at participating attractions, cafés, and shops. Don’t miss this nostalgic ride through the Isle of Wight!
Music lovers can groove to Legend – The Music of Bob Marley live at Shanklin Theatre on May 16th. Enjoy the timeless classics of reggae in a lively and vibrant show. Book your tickets on the website here.
Isle of Wight Takeover is an annual highlight for car enthusiasts, showcasing a spectacular array of vehicles and celebrating a shared passion for cars. This popular event takes place at the Royal Isle of Wight Agricultural Society County Showground and draws visitors from across the island and beyond. Buy your tickets here.
Cowes Fringe Festival lights up the town every May with music, theatre, and comedy. From lively pop and soulful tunes to captivating theatre, the festival showcases both local and national talent. Set against Cowes’ scenic coastline, it’s a must-visit Isle of Wight event for culture and entertainment lovers.
Three Rivers Music Festival returns to Durrants Farm in Porchfield on the Isle of Wight from May 29th to 31st. Set against the farm’s scenic riverside backdrop, the festival is a celebration of live music, creativity, and community.
With performances from local and national artists, art installations, and family-friendly activities, it’s a vibrant event that brings together residents and visitors alike for a memorable weekend of culture and entertainment.
Tickets can be purchased here.
