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Isle Of Wight Events Guide — May 2026
- Dominic Kureen
- May 4
- 2 min read
Spring has well and truly sprung, the weather is improving and the events calendar is heating up with it.
Here's the best of May to keep your eyes, ears and noses peeled for!
😂 The Comedy Social
📅 Friday 8th May
📍 Northwood House, Cowes
🕒 Evening
💷 Ticketed
🎤 Stand-up comedy in a relaxed social setting—expect big laughs.
🚛 Monster Truck Motorfest Isle Of Wight
📅 Saturday 9th - Sunday 10th May (10am - 10pm)
📍 Island venue (see website)
🕒 Various
💷 Ticketed
🔥 High-octane monster truck action and family entertainment.
🍎 Summer Cider And Sausage Festival
📅 Saturday 16th May
📍 Isle Of Wight Steam Railway
🕒 All day
💷 Ticketed
🌭 A celebration of cider, sausages, and steam—simple pleasures done right.
🎶 Legend – The Music Of Bob Marley
📅 Saturday 16th May (7:30pm)
📍 Shanklin Theatre
💷 £29.50
🎵 A high-energy tribute to the reggae legend.
🚶♀️ Stories Underfoot: Woolf In Freshwater
📅 Sunday 17th May (10:30am)
📍 Albion Hotel, Freshwater
💷 £10
📖 A guided storytelling walk inspired by Virginia Woolf.
🎧 Sunday Skool – Over 30s Clubbing
📅 Sunday 17th May (2pm–7pm)
📍 Strings Bar & Venue, Newport
💷 Ticketed
🕺 Daytime clubbing for grown-ups—nostalgia and dancefloor classics.
🎭 Cowes Fringe Festival
📅 Friday 22nd – Sunday 24th May
📍 Cowes (multiple venues)
💷 Various / Some free
🎨 Comedy, theatre, music, and arts in a vibrant fringe atmosphere.
🎨 Isle Of Wight Open Studios
📅 Friday 15th – Monday 25th May
📍 Island-wide
💷 Free entry to most studios
🖌️ Meet artists in their creative spaces across the island.
🎪 Three Rivers Festival
📅 Friday 29th – Sunday 31st May
📍 Durrants Farm, Porchfield
💷 Various
🎶 Music, camping, food, and festival vibes to round off the month.
🌞 Summer Fayre
📅 Saturday 30th May (10am–4pm)
📍 Victoria Recreation Ground, Newport
💷 Free Entry
🎡 A traditional fayre with stalls, entertainment, and family fun.
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