Isle of Wight Events 2019

Whatever your interests, there is always plenty to see and do here on this wonderful holiday island. As you will see, the Island is not just a holiday destination for the Spring and Summer, try a visit in the Autumn and Winter too - you will not be disappointed. Every year the events on the Isle of Wight get better and better and bigger and bigger, so read on to find out what's on in 2019!


Thursday 24th January
Acoustic Live at Woods Kitchen

Acoustic Live is Back on 24th January 2019 with Greg Barnes and friends, an evening of live soft Acoustic music.

If its food or just drinks your after come along and enjoy the free entertainment!


Friday 25th January
Cook Schools at Thompsons - Newport

If you’re looking to pick up some tips and add to your culinary repertoire then this is for you!

Drawing on Robert’s fresh and experienced approach, you will get to see how different dishes are put together from scratch. Suitable for everyone.


Saturday 26th January 7pm
CONCERT - All Saints Church, Ryde

Don't miss this opportunity to hear the acclaimed Camerata Chamber Choir joined by soloists and musicians from the mainland for a sumptuous concert.

The programme will include the popular work 'Beatus Vir by Monteverdi and Mozart's Missa Brevis.


Sunday 27th January
Chessell Chase - Freshwater

The Chessell Chase is a brand new event for 2019 hosted by West Wight Sports & Community Centre and Chessell Pottery Cafe. The off road duathlon will start and finish at Chessell Pottery Cafe with a run to West Wight Sports & Community Centre.



Wild Front + Jeph
Sat 2nd February 7.30pm
@Strings Bar & Venue - Newport

Fresh from their amazing main stage set at last years IOW Festival... Come see and hear the south coast band they're all talking about...."WILD FRONT" Southampton's finest with support from Jeph.

Find them on Facebook click here

Isle of Wight Acoustic Isle Festival

Acoustic Isle builds on the Island’s strong music and rock festival heritage and showcases the very best of local talent which thrives on the culture rich Isle of Wight. Featuring over 100 Live and Acoustic performances over 10 nights, the venues range from intimate friendly pubs, bars, cafes and restaurants in some of the Island’s most stunning locations.

The Island already boasts two of the biggest events on the summer calendar with the Isle of Wight Festival and Bestival; "Acoustic Isle" gives those festival-goers and many others the chance to come back and enjoy the "unplugged" ambience of the Isle of Wight from the comfort of a bar stool! The festival offers music lovers of all genres a great excuse for a perfect break.


February 14th to 24th
Monkey Haven - Newport

Feel the love at Monkey Haven this half term! We're all of a flutter and hope that you'll come and celebrate Love Week with us this half term! We've got animal rescue stories to warm your heart, plus the daily Keeper talks will focus on love, love, love, in its many forms.



February 15th to 23rd
Spirit of The Orient - Robin Hill

A stunning spectacle of Oriental themed light, sound and entertainment will mark the Chinese New Year at Robin Hill’s award-winning ‘electric woods’. Visitors can experience the park’s mystical woodland illuminated with a far eastern twist to capture the spirit of one of the world’s most popular celebrations. For more information, visit:


Sunday 24th March
Isle of Wight Grand National and Ashey Scurry

The Isle of Wight Grand National and Ashey Scurry is a series of amateur horse races over cross country, post and rail and natural hedges. The event takes place at West Ashey Farm, near Ryde. The course can be reached by car or by steam train from Havenstreet Station. A great family day out.



Sunday 31st March
Mothers Day Special at Isle of Wight Steam Railway - Havenstreet, Ryde

Give mum a relaxing treat this Mothers Day and treat her to a relaxing trip through the spring countryside. Treat her to lunch with our afternoon carvery, being served between 12noon - 4pm.


Sun 7th April
Memorial Ploughing Match

The Memorial Ploughing Match is in aid of the Earl Mountbatten Hospice and will be held at New Wolverton Farm in Shorwell. The event includes heavy horses ploughing, plus vintage and conventional ploughing. Free entry. Website


11th - 13th April
Isle of Wight Children's Festival

A new Isle of Wight Children's Festival will take place at the Quay Arts Centre in Newport on the Isle of Wight.


Friday 12th April
Medina Theatre, Newport

The Drifters were created in 1953 by George Treadwell & Clyde McPhatter. George Treadwell managed the group and laid the foundation of what would make The Drifters one of the greatest groups of all time.


19th and 20th April
Jack up the weekend - Newport

Jack Up The Weekend presents two great headline bands performing live in concert on two consecutive nights over the Easter Bank Holiday weekend!

On Good Friday, 19th April 2019, From The Jam, a firm Jack Up The 80s favourite guaranteed to blow you away with their electrifying live performance. Expect all The Jam hits from this outstanding musical act featuring legendary former 'The Jam' bassist Bruce Foxton.

On Easter Saturday, 20th April 2019, the sensational Big Country will be visiting the Island for this one-off exclusive. The band are no stranger to the main stage at the Isle of Wight Festival, boasting a stunning catalogue of stirring worldwide hit songs.


19th to 22nd April
Easter Fun
at Isle of Wight Steam Railway

Treat yourself to a day out over Easter by enjoying the blossoming springtime countryside from a steam train. For the kids, children's entertain Greg Chapman will amuse with juggling, stories and general antics.



Sat 4th - Sun 5th May
Isle of Wight Challenge

Enjoy the spectacular Island scenery as you run, jog or walk either the 56km ‘Half-Island’ course or the full 106km coastal loop. Join this charity challenge in aid of a number of great causes as a team of friends, colleagues or family, and support each other, or on your own, and meet fellow challengers along the way.


Sat 4th - Mon 6th May
Isle of Wight Real Ale Festival

Relax in the ambience of Havenstreet Station with a pint of your favourite tipple as you watch the trains go by! The Spring Real Ale Festival features beers sourced from brewers on the Isle of Wight and from around the country. A selection of food will also be available.


Sunday 5th May
Isle of Wight Randonnee

The Isle of Wight Randonnee is a non competitive cycle ride established by the Wayfarers in 1985.


4th May - 19th May
The Isle of Wight Walking Festival

The Isle of Wight Walking Festival has been held on the Island every May since 1999 and is the largest walking festival in the UK. It is an extremely popular event and attracts huge numbers from all over the world. The festival offers numerous guided walks that cater for all ages and abilities. Included in the festival is "Walk the Wight", a long distance sponsored walk, with proceeds going to the Earl Mountbatten Hospice. For full details of all walks, visit:


Sat 11th May
Wolverton Folk & Blues Fair

The ninth annual Wolverton Folk & Blues Fair will take place in the stunning grounds of Wolverton Manor, Shorwell, Isle of Wight on Saturday 11th May 2019.



28th May - 2nd June
Isle of Wight Jazz Weekend 2019

The Isle of Wight Jazz Weekend is the best established jazz festival in Hampshire and the Isle of Wight, regularly attracting star names from all around the UK and further afield including the USA and Australia. Taking place in half term week, it is popular with locals, holidaymakers and jazz fans who make a trip to the Island especially for the chance to see some of the best jazz singers and musicians around.

Head on over to the website for a full set of listings and venues.



Saturday 1st June
Isle of Wight Festival of Running


The Isle of Wight Festival of Running has been designed with the whole family in mind - With a fun run for children and a range of runs for adults. There is on site camping and a variety of refreshments available.


Yarmouth Old Gaffers Festival

Three days of free entertainment, craft stalls, live music and much more. The Old Gaffers, so called because of the traditional gaff rig, travel from all over the country to participate in these wonderful festivities held in the ancient town of Yarmouth. The Old gaffers is one of the most popular events on the Isle of Wight.

Yarmouth Old Gaffers Festival Website:


Thu 13th - Sun 16th June

Major UK music festival held over three days at Seaclose Park in Newport. The Isle of Wight Festival is one of the most well known Isle of Wight events and this year's line-up features the usual top acts.

For full line-up and ticket info visit:


Sat 29th June
Round the Island Race 2019

The Round the Island Race is sailing’s answer to the London Marathon as 1600 boats, crewed by some of the biggest names in sailing as well as keen amateur sailors, skim past The Needles, the Island’s distinctive rocky structure, round St Catherine’s Point and Bembridge Ledge and back into the Solent. The fleet then makes its way either side of No Man's Land Fort and across Osborne Bay to the finish line back at Cowes.

Round The Island Race Website:


Saturday 29th June
Isle of Wight Mardi Gras - Ryde

IW Mardi Gras is a carnival with a fantastic themed parade. It will feature 800 children and young people in fabulous carnival costumes performing some great choreography.


Sunday 30th June

Revamp is a family festival in Ryde on the Isle of Wight that provides entertainment of local artists, bands and DJs.  Other entertainment includes a comedy tent plus a variety of activities for the whole family. 

The festival is also committed to supporting local chairites.


Sunday 30th June
Royal Isle of Wight County Show

A fantastic day out for all the family. This is the show where cattle, sheep, pigs and poultry come first. A chance to experience our wonderful farming heritage and local produce first hand in a day that combines entertainment and fun.

website: click here



12th July - 14th July
Three Gates Farm, Calbourne

The Isle of Wight's most original, fun-filled, family friendly festival returns to Calbourne for its 10th consecutive year. With an unsurpassed reputation for bringing together a diverse, rich mix of high quality music and family entertainment, Rhythm Tree 2019 will showcase an increasingly diverse range of music with musicians from the Island, UK and beyond.


13th - 20th July
Panerai British Classic Week

Panerai British Classic Week, the premier classic yacht regatta in the UK. The annual Regatta of the BRITISH CLASSIC YACHT CLUB will see the 18th edition in 2019.  It has been held every year since the America's Cup Jubilee in 2001 and not only attracts entries from Britain but also regularly from Europe, and in 2016 & 2017, from Australia and New Zealand. The regatta is an occasion for classic boat enthusiasts to enjoy good racing and to spend time with other sailors who share the same appreciation of classics.



Charles Stanley Classics Week
Sat 27th July - Fri 2nd August

Charles Stanley Direct Cowes Classics Week is all about racing traditional yachts on the water and enjoying fabulous social events ashore.

Metre boats, Classic Racing Dayboats, Classic Yachts, Old Gaffers and Spirit of Tradition Yachts are all welcome to sail varied courses set in the Solent with free high teas, great value parties and suppers at different club venues.


Newport Main Carnival
Thursday 25th July

Sandown Children's Carnival
Fri 26th July

Sandown Main Carnival
Sat 27th July



1st - 4th August

New family festival in 2019 on the Isle of Wight - TV legends, Dick & Dom Present The Great Wonderfest that takes place between the 1st August and the 4th August. 


Sat 3rd - Sun 4th August
Chale Show

Fun for all the family with free parking. Events and entertainment over the two days includes horticultural marquees, stalls, entertainments, craft, antique, indoor market, side shows and food & drink outlets with a licensed area. For further information visit:


Sat 10th and Sun 11th August
Jack up the summer

The hugely popular Jack Up The 80s festival is returning to the Isle of Wight this Summer, with a new name and a new venue.

Sat 10th - Sat 17th August 2019
Lendy Cowes Week

Cowes Week is probably the most well known of all Isle of Wight events, with around 1000 boats and 8500 competitors taking part in this world famous sailing regatta. With its exciting racing schedule and superb shore side activities, Cowes Week offers something for everyone.


Freshwater Carnival
Sat 3rd August

Shanklin Children's Carnival
Tues 6th August

Shanklin Main Carnival
Wed 7th August

Cowes Main Carnival
Thurs 8th August

Shanklin Illuminated Carnival
Sat 10th August

Ventnor Main Carnival
Wed 14th August

Ventnor Childrens Carnival / Fireworks
Wed 14th August

Ventnor Illuminated Carnival
Sat 17th August

Yarmouth Carnival Week
Sat 17th - Sat 24th August

St. Helens Carnival
Sat 24th August


Sat 17th - Sun 18th August
The Garlic Festival

The Garlic Festival is held at Newchurch Showground, next to the Fighting Cocks pub at Arreton on the Newport to Sandown road. As well as the world famous Isle of Wight garlic, the very best of Island produce is also showcased, with over 300 stalls selling food and a diverse range of arts and crafts, plus live music.


29th August - 1st September

The brand-new annual festival of open-air picnic concerts at Northwood House, Cowes celebrating the Isle of Wight's music, food and people, featuring red squirrels, free arts workshops and the inaugural 'Proms Art & Sculpture Exhibition'

There has never been a music festival like this on the IOW, catering to lovers of both classical music and musical theatre.

The 4-day festival will take place on 29th August 2019 to 1st September in the grounds of Northwood House, Cowes as well as inside the grade II* listed Georgian manor house.



Fri 13th - Sat 14th September
Little Britain Challenge Cup Regatta

The Little Britain Challenge Cup is the largest corporate yachting regatta in Europe, as well as the biggest UK gathering of senior figureheads from the construction and property industry. The regatta is held at Cowes and is one of the industry´s top social sporting events of the year.


Saturday 21st September

A carnival of events across the Island to celebrate all that is good and magical about the Isle of Wight.

Live entertainment, parades, food and drink and parties across the Island, you'll want to make sure you're here for this celebration. Special offers in restaurants, cafes, visitor attractions and some fabulous accommodation and travel deals too. Created in 2016, this will be the fourth year we're celebrating, and events promise to be bigger and better than ever before.


IOW Cycling Festival 2019 - TBA

Every year the Island hosts the Isle of Wight Cycling Festival, which features several different cycling events for all abilities and disciplines. Races include an on-road 70 mile round the Island race known as Cycle the Wight and Sink or Swim, where home made pedal powered craft attempt to cross the River Medina! For the more resilient cyclist, the three, seven and 14 hills challenges known as "The Hills Killer" are a real test of stamina.



Saturday 26th October
Vegan & Lifestyle Show - Cowes

We are excited to be organising the first Vegan Lifestyle Show on the Isle of Wight on Saturday 26th October 2019. The show is aimed at individuals who are already vegans and also those who are interested in learning more about a vegan diet and lifestyle. We like to think that it is for the dedicated and the curious.


Isle of Wight Marathon 2019 TBC

Held since 1957, the Isle of Wight Marathon starts (11.00am) and finishes at Ryde. Medals awarded to all finishers.


Autumn Walking Weekend

A great programme is available with over 60 walks to choose from. Come and enjoy the Island's breathtaking autumnal scenery and join in one of the guided walks, all led by knowledgeable and friendly walk leaders.



Sandown Lantern Parade
and Fireworks


Victorian Christmas at Osborne House

Step back in time and experience a traditional Victorian Christmas at Osborne House in East Cowes where you will see Queen Victoria´s holiday home dressed for the festive season. Delight at the Dickensian characters and enjoy carol singing and traditional entertainment. Booking is essential for groups.

For prices and tickets call 0870 333 1183.


Cowes Christmas Carnival

Visit: for full details.


IOW Events

for more Island events, please click above graphic

Images and content courtesy of Isle of Wight Tourist Guide
and visitisleofwight Tourism websites