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May eventsEvents in Isle-of-Wight

Isle-of-Wight Events in May

Trending Isle-of-Wight May Events

Burlesque by the Sea at Staggeringly Good Brewery

Burlesque by the Sea

Saturday 2nd May

7:30pm - 10:30pm

Staggeringly Good Brewery, Portsmouth

Burlesque by the Sea

Staggeringly Good Brewery, Portsmouth

A night of burlesque, cabaret, drag, comedy, music and fun.

Isle Of Wight Dance Weekender at Robin Hill

Isle Of Wight Dance Weekender

Sat 9th - Sun 10th May

12:00pm - 10:00pm

Robin Hill, Newport

Isle Of Wight Dance Weekender

Robin Hill, Newport

The Isle of Wight Dance Weekender lands this May, bringing two days of high-energy music to the Isle of Wight.

Monster Truck Motorfest Isle of Wight at Royal Isle Of Wight Showground

Monster Truck Motorfest Isle of Wight

Sat 9th - Sun 10th May

10:00am - 7:30pm

Royal Isle Of Wight Showground, Cowes

Monster Truck Motorfest Isle of Wight

Royal Isle Of Wight Showground, Cowes

Get ready for Monster Truck Motorfest Isle of Wight 2026! The UK's wildest family motor show and the perfect family day out! Not to be missed!

Toots and the Maytals-Feat Leba Hibbert at The 1865

Toots and the Maytals-Feat Leba Hibbert

Monday 11th May

7:00pm - 10:00pm

The 1865, Southampton

Toots and the Maytals-Feat Leba Hibbert

The 1865, Southampton

AGMP Concerts presents Direct from Jamaica TOOTS AND THE MAYTALS featuring Leba Hibbert

The Chris Stapleton Experience at South Parade Pier

The Chris Stapleton Experience

Friday 15th May

6:00pm - 10:00pm

South Parade Pier, Southsea

The Chris Stapleton Experience

South Parade Pier, Southsea

Europe's No.1 tribute to Country Music Superstar, Chris Stapleton is coming to Southsea. Authentic sounds and Country music fun

EXTC 'This is Pop' at The 1865

EXTC 'This is Pop'

Friday 15th May

7:00pm - 11:00pm

The 1865, Southampton

EXTC 'This is Pop'

The 1865, Southampton

XTC's legendary drummer, Terry Chambers, is back on the road with his band EXTC (named and approved by XTC frontman, Andy Partridge).

DAY SESSIONS Presents: SILENT DISCO - Portsmouth - 2026 at Portsmouth Cathedral

DAY SESSIONS Presents: SILENT DISCO - Portsmouth - 2026

Saturday 16th May

3:30pm - 10:00pm

Portsmouth Cathedral

DAY SESSIONS Presents: SILENT DISCO - Portsmouth - 2026

Portsmouth Cathedral

Join us for an unforgettable Silent Disco experience, set within the breathtaking surroundings of Portsmouth Cathedral

Hedex Portsmouth - Yard & Warehouse at Pitt St Indoor Skatepark

Hedex Portsmouth - Yard & Warehouse

Saturday 16th May

3:00pm - 11:00pm

Pitt St Indoor Skatepark, Portsmouth

Hedex Portsmouth - Yard & Warehouse

Pitt St Indoor Skatepark, Portsmouth

One of the hottest names in Drum n Bass comes to Yard & Warehouse Portsmouth May 16th. Hedex brings the DnB madness at Pompey's best venue.

Bed By 10 | Portsmouth at The Gaiety Bar South Parade Pier

Bed By 10 | Portsmouth

Saturday 16th May

4:00pm - 8:00pm

The Gaiety Bar South Parade Pier, Portsmouth

Bed By 10 | Portsmouth

The Gaiety Bar South Parade Pier, Portsmouth

Bed By 10 heads to The Gaiety in Portsmouth!

The Style Councillors at The 1865

The Style Councillors

Saturday 16th May

7:00pm - 11:00pm

The 1865, Southampton

The Style Councillors

The 1865, Southampton

AGMP presents THE STYLE COUNCILLORS 'Our Favourite Shop' 40th Anniversary Tour

Wedding Open Morning at Voco Fareham Solent

Wedding Open Morning

Saturday 16th May

9:30am - 1:30pm

Voco Fareham Solent

Wedding Open Morning

Voco Fareham Solent

Book your one to one show round appointment and enjoy a relaxed and inspiring morning planning your perfect day.

neu waves #147 Y / House Arrest / For The Monks at The Deco

neu waves #147 Y / House Arrest / For The Monks

Thursday 21st May

8:00pm - 11:00pm

The Deco, Southsea

neu waves #147 Y / House Arrest / For The Monks

The Deco, Southsea

neu waves presents Y with support from House Arrest and For The Monks at The Deco sponsored by Southsea Sound

Bestselling Isle-of-Wight May Events

These events are selling well, grab tickets while you can...

Isle Of Wight Dance Weekender at Robin Hill

Isle Of Wight Dance Weekender

Sat 9th - Sun 10th May

12:00pm - 10:00pm

Robin Hill, Newport

Isle Of Wight Dance Weekender

Robin Hill, Newport

The Isle of Wight Dance Weekender lands this May, bringing two days of high-energy music to the Isle of Wight.

DAY SESSIONS Presents: SILENT DISCO - Portsmouth - 2026 at Portsmouth Cathedral

DAY SESSIONS Presents: SILENT DISCO - Portsmouth - 2026

Saturday 16th May

3:30pm - 10:00pm

Portsmouth Cathedral

DAY SESSIONS Presents: SILENT DISCO - Portsmouth - 2026

Portsmouth Cathedral

Join us for an unforgettable Silent Disco experience, set within the breathtaking surroundings of Portsmouth Cathedral

Hedex Portsmouth - Yard & Warehouse at Pitt St Indoor Skatepark

Hedex Portsmouth - Yard & Warehouse

Saturday 16th May

3:00pm - 11:00pm

Pitt St Indoor Skatepark, Portsmouth

Hedex Portsmouth - Yard & Warehouse

Pitt St Indoor Skatepark, Portsmouth

One of the hottest names in Drum n Bass comes to Yard & Warehouse Portsmouth May 16th. Hedex brings the DnB madness at Pompey's best venue.

Bed By 10 | Portsmouth at The Gaiety Bar South Parade Pier

Bed By 10 | Portsmouth

Saturday 16th May

4:00pm - 8:00pm

The Gaiety Bar South Parade Pier, Portsmouth

Bed By 10 | Portsmouth

The Gaiety Bar South Parade Pier, Portsmouth

Bed By 10 heads to The Gaiety in Portsmouth!

Burlesque by the Sea at Staggeringly Good Brewery

Burlesque by the Sea

Saturday 2nd May

7:30pm - 10:30pm

Staggeringly Good Brewery, Portsmouth

Burlesque by the Sea

Staggeringly Good Brewery, Portsmouth

A night of burlesque, cabaret, drag, comedy, music and fun.

The Chris Stapleton Experience at South Parade Pier

The Chris Stapleton Experience

Friday 15th May

6:00pm - 10:00pm

South Parade Pier, Southsea

The Chris Stapleton Experience

South Parade Pier, Southsea

Europe's No.1 tribute to Country Music Superstar, Chris Stapleton is coming to Southsea. Authentic sounds and Country music fun

Pola & Bryson: Overgrown Portsmouth w. Unglued / Spectral / XL at Pitt St Indoor Skatepark

Pola & Bryson: Overgrown Portsmouth w. Unglued / Spectral / XL

Saturday 30th May

8:00pm - 1:00am

Pitt St Indoor Skatepark, Portsmouth

Pola & Bryson: Overgrown Portsmouth w. Unglued / Spectral / XL

Pitt St Indoor Skatepark, Portsmouth

Pola & Bryson bring their Overgrown tour to Yard & Warehouse Portsmouth May 30th. Expect a big night of Drum n Bass

Monster Truck Motorfest Isle of Wight at Royal Isle Of Wight Showground

Monster Truck Motorfest Isle of Wight

Sat 9th - Sun 10th May

10:00am - 7:30pm

Royal Isle Of Wight Showground, Cowes

Monster Truck Motorfest Isle of Wight

Royal Isle Of Wight Showground, Cowes

Get ready for Monster Truck Motorfest Isle of Wight 2026! The UK's wildest family motor show and the perfect family day out! Not to be missed!

neu waves #147 Y / House Arrest / For The Monks at The Deco

neu waves #147 Y / House Arrest / For The Monks

Thursday 21st May

8:00pm - 11:00pm

The Deco, Southsea

neu waves #147 Y / House Arrest / For The Monks

The Deco, Southsea

neu waves presents Y with support from House Arrest and For The Monks at The Deco sponsored by Southsea Sound

Monrroe & Duskee | Big Enough Reason Tour | Portsmouth at KOLA ‘formerly Moonshine Club‘

Monrroe & Duskee | Big Enough Reason Tour | Portsmouth

Saturday 23rd May

5:00pm - 12:00am

KOLA ‘formerly Moonshine Club‘, Southsea

Monrroe & Duskee | Big Enough Reason Tour | Portsmouth

KOLA ‘formerly Moonshine Club‘, Southsea

On Saturday 23rd May, Monrroe & Duskee's Big Enough Reason UK Tour lands at Portsmouth's home of underground Drum & Bass, KOLA Club.

Toots and the Maytals-Feat Leba Hibbert at The 1865

Toots and the Maytals-Feat Leba Hibbert

Monday 11th May

7:00pm - 10:00pm

The 1865, Southampton

Toots and the Maytals-Feat Leba Hibbert

The 1865, Southampton

AGMP Concerts presents Direct from Jamaica TOOTS AND THE MAYTALS featuring Leba Hibbert

Wedding Open Morning at Voco Fareham Solent

Wedding Open Morning

Saturday 16th May

9:30am - 1:30pm

Voco Fareham Solent

Wedding Open Morning

Voco Fareham Solent

Book your one to one show round appointment and enjoy a relaxed and inspiring morning planning your perfect day.

The ultimate guide to May events in Isle-of-Wight

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