What’s On in Cowes & the Isle of Wight – 2026

Planning a stay on the Isle of Wight in 2026? From sailing and festivals to walking, running and food events, there’s always something happening here – and Cowes is perfectly placed to enjoy it all.

Below are some of the key dates to pop in your diary if you’re thinking ahead.

Where to Stay for Isle of Wight Events

Many of these events book up well in advance, especially Cowes Week, Round the Island Race, and summer weekends. Staying at The Caledon puts you within easy walking distance of Cowes town, the Red Jet ferry and waterfront action.

👉 Tip: If you know your dates, it’s always best to book early – and booking direct with us guarantees the best rates.

Winter & Early Spring

19–21 February
🎬 IW Story Festival – Talks, writers, performances and creative events across the island.

21 February
🧘 Mind Body Soul Event – Northwood House, Cowes. A wellbeing-focused day with talks, movement and inspiration.

Spring Highlights

22–24 May
🎭 Cowes Fringe – Live music, comedy and performances in venues around Cowes.

9–17 May
🥾 Isle of Wight Walking Festival (Spring) – Guided walks showcasing the island’s best scenery.

10 May
🚶 Walk the Wight – A classic island challenge raising funds for Mountbatten Hospice.

31 May – 7 June
🏃 Isle of Wight Festival of Running – From fun runs to longer distances, based in Ryde.

Summer Events

18–21 June
🎶 Isle of Wight Festival – One of the UK’s biggest music festivals, held at Seaclose Park, Newport.

11 July
⛵ Round the Island Race – A spectacular sailing event passing right by Cowes.

17–26 July
🎨 Ventnor Fringe Festival – Arts, theatre, comedy and music across Ventnor.

1–7 August
⛵ Cowes Week – The world’s largest sailing regatta and Cowes at its most vibrant.

15–16 August
🧄 Garlic Festival – A fun, food-filled weekend celebrating all things garlic (and more).

Autumn

6 September
🚴 Isle of Wight Randonnee – A popular cycling challenge around the island.

3–11 October
🥾 Isle of Wight Walking Festival (Autumn) – Cooler days, quieter paths and stunning coastal walks.

Looking for somewhere to stay in Cowes for an event?
Check availability at The Caledon

This page is updated annually with key dates as they’re confirmed.