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Events on the Isle of Wight

Pack your island holiday with fun things to do

The Isle of Wight is one of the UK's most exciting destinations for festivals and events! There's a wide variety of year-round activities and events, including one of the UK's biggest and best known music festivals, the world's oldest sailing regatta, and a food festival dedicated to one of our most famous exports, garlic!

Event Calendar

Location
Category
Sep 1-30
Dancing Man Brewery, formerly the Wool House
Entertainment

Love The Old Town

Celebrate Southampton's Old Town this September, where every street tells a story, every building has a past, and every visit offers something new. Discover independent shops, mouth watering menus, live music, craft beer and more... 

All Day
Oct 4-12
Isle of WIght Walking Festival
Walking

Autumn Walking Festival

Now in it's 26th year, the Isle of Wight Walking Festival remains one of the UK’s most loved and largest walking festivals, offering over 150 walks across two nine-day events, for all ages and abilities.

Island Wide All Day
Oct 4-31
a pile of pumpkins
Entertainment

Westover Farm Pumpkin Patch

Embark on an autumn adventure at Westover Farm this October!

Calbourne 9:30am - 4:30pm
Oct 4
Dash in the dark
Entertainment

Dash in the Dark Isle of Wight

Dash in the Dark is returning to The Royal Isle of Wight County Showground on Saturday 4 October 2025. Gather your glow gang and get ready to walk, jog, run or dance your way around this special night time mission!

Cowes 5:30pm -
Oct 9-12
isle of wight literary festival flag
Arts, Crafts & Culture

Isle of Wight Literary Festival

Enjoy engaging talks by over 50 celebrated speakers from the worlds of football, showbiz, true crime, comedy, design, and more!

Cowes All Day
Oct 11-12
a pint of stout and a pint of ale
Entertainment

Beer & Steam at IW Steam Railway

With a huge selection of tipples, join Isle of Wight Steam Railway at Havenstreet Station for a celebration of beer and steam!

Havenstreet All Day
Oct 11-12
wightrider
Entertainment

Wightrider

The Isle of Wight Bus and Coach Museum are presenting their Wightrider weekend on Saturday 11th and Sunday 12th October 2025.

Island Wide All Day
Oct 12
Sandown Pier and Culver
Entertainment

Steps to Remember Walk

In Support of Dementia UK Admiral Nurses IW Join the Steps to Remember Walk—a meaningful event bringing the community together to support families affected by dementia. 

Sandown All Day
Oct-Nov 18-2
monkey with pumpkins
Entertainment

Half Term Halloween Fun at Monkey Haven

Get ready for a spook-tacular time at Monkey Haven this half-term! A frightfully fun Halloween celebration filled with creepy creatures, creative crafts, spooky trails, and delicious themed treats. 

Newport - All day

Customer Reviews

1 2 3 4 5
Clear information, good communications, easy to contact for amendments, straight forward when using service, including on the day guidance etc.
Tue, Sep 30 2025
1 2 3 4 5
Excellent
Mon, Sep 29 2025
1 2 3 4 5
The service was great. In the pet lounge on the bench closest to the front of the ship one of the phone charging stations wasn’t working.
Mon, Sep 29 2025