Best events on the Isle of Wight holiday cottages

Best events on the Isle of Wight

Elianne Reed 28 June 2019

The Isle of Wight is a great holiday destination in all senses of the word. Beautiful beaches, wonderful walks along scenic coastal paths, stunning natural landmarks and family-friendly attractions all make this little island the go-to place for a break at any time of year.

It’s not all about the gorgeous places to visit either – the island is host to a selection of vibrant events throughout the year. From food festivals showcasing the local garlic and music festivals for all tastes, to Christmas extravaganzas and one of the most famous sporting competitions in the world, the Isle of Wight doesn’t disappoint with its unique, vibrant calendar of events.

There are so many amazing things to attend it’s impossible to mention them all, but reading through our guide to the best events and festivals in the Isle of Wight will start you off.

Cowes Week, West Cowes

sailing boat

Try to visit the Isle of Wight during the famous Regatta, the oldest and largest in the world. Held every summer, hordes of visitors descend on the town to watch an array of sailing boats competing. Over 100,000 spectators and 8,000 competitors make for a vibrant atmosphere and there is also a whole host of events that take place in and around the harbour, with food stalls dotted about and the famous beer tent!

The firework display on the final Friday of this week-long event is a much-loved tradition and rounds off the celebrations with a bang... so make sure you stay for this.

When you should pack your bags: August

The Wight Proms, Cowes

Wight Proms
 From Instagram - @northwoodhouse_iw


Look out for this festival of open-air picnic concerts where you can celebrate four days of classical music as well as a selection of cinema and comedy. The wonderful location of Northwood House in Cowes gives the event a nostalgic vibe and makes a wonderful setting for mouthwatering picnics in the fresh air.

Children love this event, especially when it’s time to wave the British flag – and you can take the opportunity to get them interested in classical music from an early age while they are having fun.

When you should pack your bags: August/September

Isle of Wight Garlic Festival, Sandown


There are many food festivals across the island, but none so pungent as the superb annual Garlic Festival, held over a weekend every August since 1983. Walk around the stalls and try the mountains of locally made garlicky delights, purchasing some as you go along. Foodies can watch live cookery demos to find out how to incorporate this little wonder into their own cooking and take away some top tips from the master chefs.

Those who are not aficionados of this little bulb may be surprised to hear that there is a multi-award-winning garlic farm on the Isle of Wight itself and this is much celebrated during the festival. It’s not all about garlic though, there’s also a funfair, live music and craft stalls to browse. Dress up if you like, you won’t be out of place – this festival is delightfully eccentric and inclusive.  If you want more of an insight into this fascinating festival, browse our blog on the Isle of Wight's connection to garlic.

When you should pack your bags: August

Victorian Christmas at Osborne House, East Cowes

Osborne House Christmas Fair
From Instagram - @ali_m_atkinson


Nobody celebrated the festive season better than the Victorians, and the tradition continues at Queen Victoria and Prince Albert’s summer residence every festive season. The stunning Osborne House makes a wonderful backdrop to a glittering carousel which will be sure to transport you back to days gone by.

Follow the scent of the roasting chestnuts in the snowy courtyard and have a go at the old-fashioned games, before meeting Father Christmas and some famous Dickensian characters as you tour the rooms. Sing along to your favourite Christmas carols with the choir and experience a Victorian Christmas after dark with sparkling festive lights in the grounds.

When you should pack your bags: December

The Isle of Wight Festival, Newport

people dancing at festival

Start the summer music festival season with this much-loved event. There are many reasons for coming to the Isle of Wight, but this is one of the most popular and no wonder. With past acts headlining such as Rod Stewart and Rag’n’Bone man alongside the debut performances of some of the hottest up-and-coming artists, the festival is recognised around the world as a real contender. The acts confirmed for 2019 include Noel Gallagher’s High Flying Birds and George Ezra, so book your tickets quickly.

When you should pack your bags: June

The Isle of Wight Scooter Rally, Ryde

Isle of Wight Scooter Rally
From Instagram - @bagged_benz


Scooter fanatics should zoom to the biggest gathering of scooters in the world to see all things um.. scooter. It’s as simple as that, but far bigger than you could imagine. Up to 5,000 riders of classic vintage and modern scooters descend on the island, mainly to Ryde and Sandown, to the cheers of islanders and tourists waving them by. Once the motors have passed, it’s not over – there is music all over the weekend on the seafront in Ryde.

When you should pack your bags: August

Isle of Wight Literary Festival, Cowes

author signing a book

Though the island hosts an eclectic programme of cultural festivals and events throughout the year, the main event on the artistic calendar has to be the much-acclaimed Literary Festival, aimed at increasing the cultural richness of the Isle of Wight.

With a star-studded cast of literary and artistic talent, the sessions are intimate so that you really feel part of the action. Author presentations and interviews are a favourite and most genres are covered, including history, maritime adventure, crime fiction and medicine.

When you should pack your bags: October

Brighstone Christmas Tree Festival, Brighstone

Brighstone Christmas Tree Festival
From Instagram - @lizzies_way


Start the festive season off with a trip to visit the themed trees at this hugely popular annual festival. Over 200 ‘themed’ trees are dressed up for visitors to marvel at, as well as a myriad of activities put on for all the family. Dotted around seven very different locations, there are also children’s trees in the library and the opportunity to visit Santa in his Winter Wonderland on the Saturday and Sunday.

After you have seen the trees dressed up in all their glory, finish with the charity ‘Lights of Love’ carol service in Brighstone Church, sure to get you in the holiday mood.

When you should pack your bags: December

Also keep am eye out for:



  • Mardi Gras in Ryde - a colourful carnival with a brilliant themed parade – bring a bit of Brazil into your life!
  • Round the Island Race in West Cowes – 1,600 boats captained by both pros and amateurs make their way past the iconic Needles as they race to the finish.
  • Rhythmtree Festival in Calbourne – a fun-filled, family-friendly festival, loved by locals and tourists alike.
  • Revamp Festival in Ryde – a family orientated event showcasing local artists, DJ’s, bands and comedians.
  • Royal Isle of Wight County Show – celebrate the best of the island with animals, tractor rides, sheep shearing and show jumping.
  • Ventnor Fringe – a unique celebration of Wight talent across many creative disciplines; great for those who love up-and-coming artists.
  • Osborne Horse Trials – a fabulous and exciting competition to compete in or watch, it also has lots of fun family activities for those who aren’t equine orientated.
  • Newport and Sandown Main Carnivals – get a bit of carnival fever into your life with these colourful and vibrant processions in two of the island’s main resorts.
  • Isle of Wight Jigsaw Puzzle Festival – hundreds of already made up jigsaws – you won’t get bored as every time a puzzle sells, another takes its place!
  • Festival of Light Inspired by Diwali – a spectacular show of light and colour in ancient woodland – a truly magical celebrating of this wonderful festival.
  • Halloween of the Isle of Wight - so many of the island's attractions run fantastic events for Halloween, from pumpkin picking to ghost tours, there's something for everyone.


** Please note that while some of the larger festivals are firm fixtures on the island’s event calendar, the smaller events may change year to year **

Whether you’re coming for a few days for a specific event or you want to incorporate one of these fabulous festivals during a longer holiday, base yourself at one of our holiday cottages on the Isle of Wight and start the day in style. Stay in a cute coastal cottage for two, a country retreat just perfect for celebrating a special occasion or a property nearer the action in one of the major towns of the island. Enjoy the events and festivals with us!

Disclaimer: Whilst every effort has been made to ensure the accuracy of the information at the time of writing, please ensure you check carefully before making any decisions based on the contents within this article.

Like it? Share it...

Read more like this

The ultimate guide to Sandown

Eating and drinking, getting outside and where to take your kids and dogs in Sandown.

The best dog-friendly pubs on the Isle of Wight

Including everything from 17th-century taverns in the countryside to modern cocktail bars on a seafront promenade

Our dog-friendly guide to the Isle of Wight

The dog-friendly Isle of Wight promises a memorable holiday of walks, steam train rides and meals in pet-friendly pubs.
The Travel Chapter Limited trading as Island Cottage Holidays is an appointed representative of ITC Compliance Limited which is authorised and regulated by the Financial Conduct Authority (their registration number is 313486) and which is permitted to advise on and arrange general insurance contracts as an intermediary.
The Travel Chapter Limited trading as Island Cottage Holidays | The Travel Chapter Limited is registered in England and Wales. | Registered office Travel Chapter House Gammaton Road Bideford EX39 4DF Company No. 02431506 | VAT reg: 143053210.