Next 30 days on the Isle of Wight

Rabbit Rabbit brings Triple Cream's Chas & Dave tribute to East Cowes Town Hall for a Cowes Fringe Friday night of Rockney singalong favourites.

19:30–21:30 · Part of Cowes Fringe - Friday · East Cowes Town Hall · Booking required

Green Haze bring a high-energy Green Day tribute show to Strings Bar & Venue, with punk-rock hits and authentic stage energy.

19:30–23:30 · Strings Bar & Venue · Booking required

National Gallery masterpieces reproduced outdoors across Newport — free self-guided mile-long trail from 6 May–30 Oct 2026 (step-free route around town centre).

Ongoing · Newport · Free

Preview every participating artist in one gallery — Open Studios Showcase at Quay Arts, Newport (15–25 May 2026). Free entry during usual gallery hours; ideal route-planning stop before studio hops later in May.

During gallery hours · Part of Isle of Wight Open Studios · Quay Arts · Free

Eleven-day island-wide celebration (15–25 May 2026): ~200 artists open studios, pop-ups and galleries — paint, sculpture, print, photography, textiles, jewellery and ceramics. Wander, meet makers and plan routes from the Quay Arts showcase.

Daily 10:00-16:00 · Isle of Wight (various locations) · Free

Cowes Fringe continues with a town-wide programme of music, theatre, comedy, DJ sets, and local and national performers.

10:00–23:00 · Cowes (various locations) · £5.00 · Booking required

An Island Artisans spring market at Yarmouth Town Hall, featuring local makers and artists across art, homewares, accessories and apothecary.

Daily 10:00-16:30 · Yarmouth Town Hall

Stitches & Stories invites children to make fabric squares for a Cowes maritime quilt at East Cowes Town Hall during Cowes Fringe.

10:00–13:00 · Part of Cowes Fringe - Saturday · East Cowes Town Hall · £5.00 · Booking required

Raise a glass to the best weekend of the spring! The North East Ale Trail is the ultimate pub crawl through 14 of the island's most charming venues. From historic inns to trendy bars, discover an incredible selection of real ales and local craft brews while exploring the picturesque North East coast. It's a celebration of community, hops, and great vibes. No tickets required—just grab your trail map and start your journey! Whether you're an ale aficionado or just love a great atmosphere, this is the trail you've been waiting for. Cheers to the North East!

Ongoing · North East Isle of Wight (pub trail) · Free

Fine Chocolate & Spirits Pairing brings Helena Nicklin and Chantal Coady OBE to Bar 46 for a Cowes Fringe tasting experience.

17:00–18:30 · Part of Cowes Fringe - Saturday · Bar 46 · Paid · Booking required

Robin Hill hosts Bingo Bango II with interactive bingo, comedy, party anthems, and Say You'll Be Spice performing Spice Girls hits.

19:00–23:59 · Robin Hill · £16.96 · Booking required

Sir Derek Jacobi appears in conversation with Richard Clifford at East Cowes Town Hall for a Cowes Fringe gala evening supporting Mountbatten Isle of Wight.

19:00–22:00 · Part of Cowes Fringe - Saturday · East Cowes Town Hall · Paid · Booking required

Horse Box Theatre brings Ubu, King of the Isle of Wight to Northwood House for a wild Cowes Fringe satire inspired by Alfred Jarry's Ubu Roi.

19:00–20:30 · Part of Cowes Fringe - Saturday · Northwood House · £18.00 · Booking required

National Gallery masterpieces reproduced outdoors across Newport — free self-guided mile-long trail from 6 May–30 Oct 2026 (step-free route around town centre).

Ongoing · Newport · Free

Preview every participating artist in one gallery — Open Studios Showcase at Quay Arts, Newport (15–25 May 2026). Free entry during usual gallery hours; ideal route-planning stop before studio hops later in May.

During gallery hours · Part of Isle of Wight Open Studios · Quay Arts · Free

Eleven-day island-wide celebration (15–25 May 2026): ~200 artists open studios, pop-ups and galleries — paint, sculpture, print, photography, textiles, jewellery and ceramics. Wander, meet makers and plan routes from the Quay Arts showcase.

Daily 10:00-16:00 · Isle of Wight (various locations) · Free

Raise a glass to the best weekend of the spring! The North East Ale Trail is the ultimate pub crawl through 14 of the island's most charming venues. From historic inns to trendy bars, discover an incredible selection of real ales and local craft brews while exploring the picturesque North East coast. It's a celebration of community, hops, and great vibes. No tickets required—just grab your trail map and start your journey! Whether you're an ale aficionado or just love a great atmosphere, this is the trail you've been waiting for. Cheers to the North East!

Ongoing · North East Isle of Wight (pub trail) · Free

Vintage amusements, Jason Maverick circus shows, treasure hunt, arts and crafts, play park and steam trains at Havenstreet on Sunday 24 May.

All day · Isle of Wight Steam Railway · Free

An Island Artisans spring market at Yarmouth Town Hall, featuring local makers and artists across art, homewares, accessories and apothecary.

Daily 10:00-16:30 · Yarmouth Town Hall

Cowes Fringe closes with music, theatre, comedy, and performance across venues in Cowes against the town's maritime backdrop.

10:00–23:00 · Cowes (various locations) · £5.00 · Booking required

Theatretrain Isle of Wight performs Sing & Dance the Musicals at East Cowes Town Hall, showcasing young Island performers in a lunchtime Cowes Fringe show.

12:30–13:30 · Part of Cowes Fringe - Sunday · East Cowes Town Hall · Paid · Booking required

Karen Robb leads a Sewing Bee Competition Workshop at Northwood House for Cowes Fringe, with participants asked to bring their own sewing machine.

13:00–16:00 · Part of Cowes Fringe - Sunday · Northwood House · Paid · Booking required

Premium Wine & Chocolate Pairing brings Helena Nicklin and Chantal Coady OBE to Bar 46 for a Sunday Cowes Fringe tasting.

14:30–16:00 · Part of Cowes Fringe - Sunday · Bar 46 · Paid · Booking required

Theatretrain Isle of Wight's 2.30pm Cowes Fringe performance brings young musical-theatre talent to East Cowes Town Hall.

14:30–15:30 · Part of Cowes Fringe - Sunday · East Cowes Town Hall · Paid · Booking required

Sunday afternoon live music at The Waterfront, Totland Bay — line-up to be confirmed on the venue poster. Source: venue poster / eatbythesea.com.

15:00–18:00 · The Waterfront

A 50th anniversary marching band tattoo at Cowes Enterprise College, bringing youth marching bands and drill display teams to Cowes for an evening show.

18:00–21:00 · Cowes Enterprise College · £12.00 · Booking required

Flats & Sharps bring contemporary acoustic music from their Always There EP to the intimate Monkton Arts venue in Ryde.

19:00–21:00 · Monkton Arts · Booking required

Cult Figure celebrates Kenneth Williams' centenary at Northwood House, with Colin Elmer reprising the comedy icon in Cowes Fringe's Sunday theatre programme.

19:00–20:30 · Part of Cowes Fringe - Sunday · Northwood House · Paid · Booking required

The Cavern Club Story comes to East Cowes Town Hall for Cowes Fringe, telling the story of Liverpool's famous music venue with live musicians and visuals.

19:30–21:30 · Part of Cowes Fringe - Sunday · East Cowes Town Hall · Paid · Booking required

National Gallery masterpieces reproduced outdoors across Newport — free self-guided mile-long trail from 6 May–30 Oct 2026 (step-free route around town centre).

Ongoing · Newport · Free

Preview every participating artist in one gallery — Open Studios Showcase at Quay Arts, Newport (15–25 May 2026). Free entry during usual gallery hours; ideal route-planning stop before studio hops later in May.

During gallery hours · Part of Isle of Wight Open Studios · Quay Arts · Free

Eleven-day island-wide celebration (15–25 May 2026): ~200 artists open studios, pop-ups and galleries — paint, sculpture, print, photography, textiles, jewellery and ceramics. Wander, meet makers and plan routes from the Quay Arts showcase.

Daily 10:00-16:00 · Isle of Wight (various locations) · Free

Bank Holiday Monday at Havenstreet brings vintage amusements, Jason Maverick circus shows, treasure hunt, arts and crafts, play park and steam trains.

All day · Isle of Wight Steam Railway · Free

An Island Artisans spring market at Yarmouth Town Hall, featuring local makers and artists across art, homewares, accessories and apothecary.

Daily 10:00-16:30 · Yarmouth Town Hall

Bembridge Lifeboat joins Bembridge Street Fair during Yellow Welly Week, with the RNLI presence in the village from 11am to 4pm.

11:00–16:00 · Bembridge Village

Bank Holiday Monday jam night at The White Horse Inn in Whitwell, with full backline and PA provided, kitchen open until 20:30 and music from 19:30.

19:30–22:30 · The White Horse Inn · Dogs welcome

National Gallery masterpieces reproduced outdoors across Newport — free self-guided mile-long trail from 6 May–30 Oct 2026 (step-free route around town centre).

Ongoing · Newport · Free

The NSRA Hot Rod Fun Run brings custom hot rods, classic street cars and cruisers to Havenstreet on Tuesday 26 May.

All day · Isle of Wight Steam Railway · Free

A Yellow Welly Week lifeboat launch and recovery evening at Bembridge Lifeboat Station, with doors open from 6.30pm and refreshments after the launch.

Launch at 7pm · Bembridge Lifeboat Station

National Gallery masterpieces reproduced outdoors across Newport — free self-guided mile-long trail from 6 May–30 Oct 2026 (step-free route around town centre).

Ongoing · Newport · Free

National Gallery masterpieces reproduced outdoors across Newport — free self-guided mile-long trail from 6 May–30 Oct 2026 (step-free route around town centre).

Ongoing · Newport · Free

Children's activities in the Offshore Boathouse at Bembridge Lifeboat Station during Yellow Welly Week, running from 10am to noon.

10:00–12:00 · Bembridge Lifeboat Station

A practical Isle of Wight Pony Club turnout demonstration at the County Showground in Northwood, covering plaiting, trimming, feed advice and in-hand presentation.

14:00–16:00 · Isle of Wight County Showground · £8.00 · Booking required

Shoreline Productions bring The Scarlet Pimpernel to Shanklin Theatre with drama, romance, adventure, and a sweeping musical score.

19:30–22:00 · Shanklin Theatre · £23.00 · Booking required

National Gallery masterpieces reproduced outdoors across Newport — free self-guided mile-long trail from 6 May–30 Oct 2026 (step-free route around town centre).

Ongoing · Newport · Free

A children's pirate parade at Bembridge Lifeboat Station during Yellow Welly Week, with fancy dress encouraged and a prize for all entries.

10:00–12:00 · Bembridge Lifeboat Station

Three Rivers Music Festival opens at Durrants Farm with live music, camping, local traders, wellness, and a grassroots community feel.

12:00–23:00 · Durrants Farm · £80.00 · Booking required

Shoreline Productions continue The Scarlet Pimpernel at Shanklin Theatre, a swashbuckling musical set during the French Revolution.

19:30–22:00 · Shanklin Theatre · £23.00 · Booking required

Billy Bibby performs The Balcony in stripped-back acoustic form at Strings Bar & Venue, with stories from writing and recording the album.

19:30–22:30 · Strings Bar & Venue · Booking required

The Jive Aces bring their swing, jive, rhythm and blues, and feel-good energy to Medina Theatre with guest singer Noelle Vaughn.

19:30–21:30 · Medina Theatre · £22.00 · Booking required

National Gallery masterpieces reproduced outdoors across Newport — free self-guided mile-long trail from 6 May–30 Oct 2026 (step-free route around town centre).

Ongoing · Newport · Free

Three Rivers Music Festival continues at Durrants Farm with bands, DJs, camping, local traders, family activities, and woodland dance stages.

10:00–23:00 · Durrants Farm · £80.00 · Booking required

England legend Peter Shilton CBE appears at Medina Theatre for career stories, audience Q&A, VIP meet-and-greet, and football memories.

18:15–21:30 · Medina Theatre · £31.50 · Booking required

The Wurzels bring Scrumpy & Western singalongs, comedy and charity fundraising to Robin Hill near Newport on the Isle of Wight.

19:00–23:30 · Robin Hill · £27.80 · Booking required

The Scarlet Pimpernel continues at Shanklin Theatre with Shoreline Productions' musical tale of disguises, rescues, and forbidden love.

19:30–22:00 · Shanklin Theatre · £23.00 · Booking required

The Jive Aces perform their high-energy swing and rock 'n' roll show at Bembridge Coast Hotel on the eastern Isle of Wight.

21:30–23:30 · Bembridge Coast Hotel · Booking required

National Gallery masterpieces reproduced outdoors across Newport — free self-guided mile-long trail from 6 May–30 Oct 2026 (step-free route around town centre).

Ongoing · Newport · Free

Raw Samba Band brings live carnival rhythms to Havenstreet on Sunday 31 May, alongside steam trains and half-term family activities.

All day · Isle of Wight Steam Railway · Free

The Isle of Wight Festival of Running begins from West Wight Sports and Community Centre with runs and activities across the west Wight landscape.

09:00–17:00 · West Wight Sports and Community Centre · Booking required

Three Rivers Music Festival closes at Durrants Farm with a final day of live music, DJs, community, camping, and rural festival atmosphere.

10:00–23:00 · Durrants Farm · £80.00 · Booking required

Sunday afternoon live music at The Waterfront, Totland Bay (Paolo on the poster). Music from 3pm; check venue for food service times. Source: venue poster / eatbythesea.com.

15:00–18:00 · The Waterfront

The Scarlet Pimpernel concludes at Shanklin Theatre with Shoreline Productions' adventurous musical of revolution and romance.

19:30–22:00 · Shanklin Theatre · £23.00 · Booking required

National Gallery masterpieces reproduced outdoors across Newport — free self-guided mile-long trail from 6 May–30 Oct 2026 (step-free route around town centre).

Ongoing · Newport · Free

A day of Isle of Wight Festival of Running activity based around Freshwater and the west Wight's coastal and countryside routes.

09:00–17:00 · West Wight Sports and Community Centre · Booking required

National Gallery masterpieces reproduced outdoors across Newport — free self-guided mile-long trail from 6 May–30 Oct 2026 (step-free route around town centre).

Ongoing · Newport · Free

The Isle of Wight Festival of Running continues with runs and running-related activities celebrating the island's west coast scenery.

09:00–17:00 · West Wight Sports and Community Centre · Booking required

National Gallery masterpieces reproduced outdoors across Newport — free self-guided mile-long trail from 6 May–30 Oct 2026 (step-free route around town centre).

Ongoing · Newport · Free

A midweek day of Isle of Wight Festival of Running activity, welcoming runners of different abilities to west Wight routes.

09:00–17:00 · West Wight Sports and Community Centre · Booking required

National Gallery masterpieces reproduced outdoors across Newport — free self-guided mile-long trail from 6 May–30 Oct 2026 (step-free route around town centre).

Ongoing · Newport · Free

The Isle of Wight Festival of Running continues with social runs and activities for runners exploring Freshwater and west Wight.

09:00–17:00 · West Wight Sports and Community Centre · Booking required

Isle of Wight punk band The Appalled launch their latest EP at Strings Bar & Venue with support from Capo Regime and And They Lived.

19:30–23:00 · Strings Bar & Venue · Donations welcome

National Gallery masterpieces reproduced outdoors across Newport — free self-guided mile-long trail from 6 May–30 Oct 2026 (step-free route around town centre).

Ongoing · Newport · Free

The Isle of Wight Festival of Running heads into the weekend with active events and social runs around the west Wight.

09:00–17:00 · West Wight Sports and Community Centre · Booking required

National Gallery masterpieces reproduced outdoors across Newport — free self-guided mile-long trail from 6 May–30 Oct 2026 (step-free route around town centre).

Ongoing · Newport · Free

The Isle of Wight Festival of Running features the Tapnell 10k as part of its west Wight programme of running events.

09:00–17:00 · West Wight Sports and Community Centre · Booking required

The Isle of Wight Tattoo Convention returns to Quay Arts with tattoo artists, competitions, live music, vendors, and creative community.

10:30–19:00 · Quay Arts · £10.00 · Booking required

A family farm open day at IOW Rare Breeds in Alverstone with tractor and trailer rides, a farm trail, animal meet-and-greets, children's crafts and refreshments.

11:00–15:00 · Isle of Wight Rare Breeds · £2.00 · Booking required

National Gallery masterpieces reproduced outdoors across Newport — free self-guided mile-long trail from 6 May–30 Oct 2026 (step-free route around town centre).

Ongoing · Newport · Free

Working-farm open day near Alum Bay with milking, farm tours, animal encounters, a nature walk, milkshakes, ice cream and food from Fat Shauns.

08:30–14:00 · Warren Farm · Booking required

The festival concludes with the Needles Half Marathon, following a scenic west Wight route from Colwell Bay to The Needles and Tennyson Down.

09:00–17:00 · West Wight Sports and Community Centre · Booking required

Isle of Wight Dubbers join St Helens Village Fayre on the village green, with VW displays, stalls, local goodies and family-friendly community fun.

09:00–16:00 · St Helens Village Green

The Isle of Wight Tattoo Convention continues at Quay Arts with UK tattoo artists, competitions, stalls, live music, and community.

10:30–19:00 · Quay Arts · £10.00 · Booking required

Sunday afternoon live music at The Waterfront, Totland Bay (The Geckos on the poster). Music from 3pm; check venue for food service times. Source: venue poster / eatbythesea.com.

15:00–18:00 · The Waterfront

A Shanklin Theatre tribute to early rock 'n' roll pioneers including Elvis Presley, Chuck Berry, Little Richard, Jerry Lee Lewis, and Buddy Holly.

19:30–22:00 · Shanklin Theatre · Booking required

National Gallery masterpieces reproduced outdoors across Newport — free self-guided mile-long trail from 6 May–30 Oct 2026 (step-free route around town centre).

Ongoing · Newport · Free

National Gallery masterpieces reproduced outdoors across Newport — free self-guided mile-long trail from 6 May–30 Oct 2026 (step-free route around town centre).

Ongoing · Newport · Free

National Gallery masterpieces reproduced outdoors across Newport — free self-guided mile-long trail from 6 May–30 Oct 2026 (step-free route around town centre).

Ongoing · Newport · Free

National Gallery masterpieces reproduced outdoors across Newport — free self-guided mile-long trail from 6 May–30 Oct 2026 (step-free route around town centre).

Ongoing · Newport · Free

National Gallery masterpieces reproduced outdoors across Newport — free self-guided mile-long trail from 6 May–30 Oct 2026 (step-free route around town centre).

Ongoing · Newport · Free

Think Floyd perform The Dark Side of the Moon and Wish You Were Here in full, plus classic Pink Floyd tracks and an immersive laser show.

19:30–22:30 · Shanklin Theatre · £33.50 · Booking required

Strings Bar & Venue hosts Grin & Tonic comedy night, headlined by multimedia comedian Ted Hill with high-energy stand-up and visual gags.

19:30–22:30 · Strings Bar & Venue · Booking required

National Gallery masterpieces reproduced outdoors across Newport — free self-guided mile-long trail from 6 May–30 Oct 2026 (step-free route around town centre).

Ongoing · Newport · Free

Craft gin and spirits weekend across the station, café and historic steam trains—tastings from Isle of Wight and mainland distillers.

All day · Isle of Wight Steam Railway

Melodic Choir presents All Sorts at Jenny Kerry Theatre, Ryde School, with a mixed programme of songs and proceeds going to Community Spirited Cafe.

19:30–21:30 · Jenny Kerry Theatre, Ryde School · £12.00 · Booking required

Big Girls Don't Cry celebrates Frankie Valli and The Four Seasons at Shanklin Theatre with live band, harmonies, and classic 60s and 70s hits.

19:30–21:30 · Shanklin Theatre · £29.00 · Booking required

Baron Strange & The Blackbyrds launch A Long Time Coming at Strings Bar & Venue, blending blues, southern rock, grunge, and rock 'n' roll.

19:30–23:30 · Strings Bar & Venue · Booking required

World-renowned DJ and producer David Morales brings house music to Northwood House in Cowes for a late-night dance event.

21:00–23:59 · Northwood House · Booking required

National Gallery masterpieces reproduced outdoors across Newport — free self-guided mile-long trail from 6 May–30 Oct 2026 (step-free route around town centre).

Ongoing · Newport · Free

Craft gin and spirits weekend across the station, café and historic steam trains—tastings from Isle of Wight and mainland distillers.

All day · Isle of Wight Steam Railway

The late-night David Morales session at Northwood House continues after midnight for the final hour of the Cowes dance event.

00:00–01:00 · Northwood House · Booking required

Sunday afternoon live music at The Waterfront, Totland Bay (Storm on the poster). Music from 3pm; check venue for food service times. Source: venue poster / eatbythesea.com.

15:00–18:00 · The Waterfront

National Gallery masterpieces reproduced outdoors across Newport — free self-guided mile-long trail from 6 May–30 Oct 2026 (step-free route around town centre).

Ongoing · Newport · Free

National Gallery masterpieces reproduced outdoors across Newport — free self-guided mile-long trail from 6 May–30 Oct 2026 (step-free route around town centre).

Ongoing · Newport · Free

National Gallery masterpieces reproduced outdoors across Newport — free self-guided mile-long trail from 6 May–30 Oct 2026 (step-free route around town centre).

Ongoing · Newport · Free

National Gallery masterpieces reproduced outdoors across Newport — free self-guided mile-long trail from 6 May–30 Oct 2026 (step-free route around town centre).

Ongoing · Newport · Free

National Gallery masterpieces reproduced outdoors across Newport — free self-guided mile-long trail from 6 May–30 Oct 2026 (step-free route around town centre).

Ongoing · Newport · Free

National Gallery masterpieces reproduced outdoors across Newport — free self-guided mile-long trail from 6 May–30 Oct 2026 (step-free route around town centre).

Ongoing · Newport · Free