Next 30 days on the Isle of Wight

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

Learn to draw and paint a piglet in pastels at The White Horse Inn, Whitwell, in the first of two Tuesday sessions on 7 July. £35 covers both mornings.

10:30–12:30 · The White Horse Inn · £35.00 · Dogs welcome · Booking required

Tuesday fish-and-chip supper with daytime trains and extended evening steam through the Island countryside.

16:00–22:00 · Isle of Wight Steam Railway

Tuesday evening fish and chip events at the Isle of Wight Steam Railway through July and August 2026.

17:00–20:00 · Isle of Wight Steam Railway · £16.95 · 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

A high-energy 1980s tribute concert at Shanklin Theatre with live band, dancers and more than thirty-five chart hits from the decade.

19:30–22:00 · Shanklin Theatre · £31.00 · 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 free community summer fayre at Shalfleet CE Primary School on Friday 10 July, 2pm to 4.30pm, with aerial tasters from Arts With Alicia, face painting, bouncy castle, tombola, and refreshments.

14:00–16:30 · Shalfleet CE Primary School · Free

Binstead Primary School Summer Fayre packs in a fire engine, helter skelter, circus skills, face painting, pizza, ice cream and a £100 cash raffle.

15:30–17:30 · Binstead Primary School · Free

A two-evening tribute music event at Retro Staycations, Ryde, on 10 and 11 July 2026.

Gates 17:30; main tribute acts 20:00. · Retro Staycations at Hazelgrove Farm · £15.00 · Booking required

Queen and Fleetwood Mac tribute acts share a summer bill at Robin Hill’s woodland amphitheatre near Downend.

18:30–22:30 · Robin Hill · £14.95 · Booking required

Hampshire Police Male Voice Choir open their Isle of Wight summer tour at Norton Grange Coastal Village near Yarmouth.

19:45–21:30 · Norton Grange Coastal Village

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

Round the Island Race 2026 sends yachts from Cowes around the Isle of Wight in one of the world’s largest one-day sailing races.

06:30–18:00 · Cowes (various locations) · Paid · Booking required

The Royal Isle of Wight County Show takes place at Northwood on Saturday 11 and Sunday 12 July 2026.

10:00–17:00 · Isle of Wight County Showground · £12.50 · Dogs welcome

A two-evening tribute music event at Retro Staycations, Ryde, on 10 and 11 July 2026.

Gates 17:30; main tribute acts 20:00. · Retro Staycations at Hazelgrove Farm · £15.00 · Booking required

Medina Community Choir brings its 20-year celebration to St Mary's Church in Cowes, with favourite songs from across the choir's history.

19:00–21:30 · St Mary's Church, Cowes · £12.00 · Booking required New

Hampshire Police Male Voice Choir perform at Christ Church Totland Bay on the second night of their Isle of Wight tour.

19:00–21:00 · Christ Church Totland Bay

Vocal Legends with Sandy Smith brings a night of big vocal hits to Apollo Theatre in Newport, covering Cher, Tina Turner, Whitney Houston, Adele and more.

19:30–21:45 · Apollo Theatre · Booking required

Three hours of salsa and bachata social dancing with The Rueda Rebel at Cafe de Ryde on Ryde Esplanade for £4 entry.

19:30–22:30 · Cafe de Ryde · £4.00

Classic Isle: Proms '26 brings the Bournemouth Symphony Orchestra to Robin Hill in Newport for an open-air summer concert.

19:30–22:00 · Robin Hill · £30.00 · 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

The July Wildheart Animal Sanctuary yoga, sound bath and Reiki session from Your Sound Guide.

08:30–10:00 · Wildheart Animal Sanctuary · £35.00 · Booking required

The Royal Isle of Wight County Show takes place at Northwood on Saturday 11 and Sunday 12 July 2026.

09:30–16:00 · Isle of Wight County Showground · £12.50 · Dogs welcome

Hampshire Police Male Voice Choir perform at 2pm during the Isle of Wight County Show at Northwood showground.

14:00–15:00 · Isle of Wight County Showground

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

15:00–18:00 · The Waterfront

Classic Isle: Night at the Movies brings John Williams and Hans Zimmer film music to Robin Hill with the Bournemouth Symphony Orchestra.

19:30–22:00 · Robin Hill · £30.00 · 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

AJ Dance Inclusive Beginner Dance returns to Ryde on 13 July, offering a calm £8.50 Monday morning class for adults starting from scratch.

10:30–11:30 · Ryde Methodist Church · £8.50 · 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

Sip and Paint in Whitwell turns to a wolf and moon blackout pastel piece on 14 July, with all materials supplied at The White Horse Inn for £35.

10:30–13:00 · The White Horse Inn · £35.00 · Dogs welcome · Booking required

Tuesday fish-and-chip supper with daytime trains and extended evening steam through the Island countryside.

16:00–22:00 · Isle of Wight Steam Railway

Tuesday evening fish and chip events at the Isle of Wight Steam Railway through July and August 2026.

17:00–20:00 · Isle of Wight Steam Railway · £16.95 · Booking required

G4 bring their sell-out musical theatre tour to Shanklin Theatre with West End and Broadway showstoppers and four-part harmony.

19:30–21:45 · Shanklin Theatre · £35.00 · 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

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

Ventnor Fringe returns from 17 to 26 July 2026 with performances and events across Ventnor.

Programme times not found. · Ventnor Town Centre

Day one of the 18+ Wytwoods music and wellness festival in the woods at Robin Hill, with camping available.

Ongoing · Robin Hill · Paid · Booking required

70 Girls 70 brings Kander and Ebb's offbeat musical comedy to Apollo Theatre in Newport, with performances from 17 to 25 July 2026.

Selected performance dates · Apollo Theatre · £5.00 · Booking required

Jim Davidson brings Last Man Standing... Just! to Medina Theatre in Newport, a 16+ comedy night with tickets listed at £30.

19:30–21:30 · Medina Theatre · £30.00 · Booking required

Dogmum premieres at Ventnor Fringe on 17 July, with Amy Ambrose bringing a late-night musical rom-com about a woman, her cockapoo and modern life.

21:30–23:00 · Ventnor Arts Club · 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

Day one of the 18+ Wytwoods music and wellness festival in the woods at Robin Hill, with camping available.

Ongoing · Robin Hill · Paid · Booking required

Ventnor Fringe returns from 17 to 26 July 2026 with performances and events across Ventnor.

Programme times not found. · Ventnor Town Centre

English Heritage Great British Summer activities run at Carisbrooke Castle from 18 July into early September 2026.

Official event continues to 6 September. · Carisbrooke · Paid

English Heritage's Great British Summer runs at Osborne House in East Cowes daily from 18 July to 6 September, with fairground activities, circus skills, puppet antics and a children's stamp passport trail.

Official event continues to 6 September. · Osborne House · Paid

A real ale weekend with an extended evening train service at the Isle of Wight Steam Railway on 18 and 19 July 2026.

Bars open from 16:00; free station entry if not travelling. · Isle of Wight Steam Railway · Paid

Isle of Wight Pride returns to Ryde on Saturday 18 July 2026 with a parade, community village and entertainment.

11:00–20:00 · Ryde

Day two of Wytwoods at Robin Hill: stages, installations and late-night music in the woodland amphitheatre site.

Ongoing · Robin Hill · Paid · Booking required

70 Girls 70 brings Kander and Ebb's offbeat musical comedy to Apollo Theatre in Newport, with performances from 17 to 25 July 2026.

Selected performance dates · Apollo Theatre · £5.00 · Booking required

Dogmum returns to Ventnor Arts Club on 18 July for a second late-night Fringe performance from Amy Ambrose, built around romance, comedy and cockapoo Alfie.

21:30–23:00 · Ventnor Arts Club · 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

Day two of Wytwoods at Robin Hill: stages, installations and late-night music in the woodland amphitheatre site.

Ongoing · Robin Hill · Paid · Booking required

Ventnor Fringe returns from 17 to 26 July 2026 with performances and events across Ventnor.

Programme times not found. · Ventnor Town Centre

Dash and Splash returns to Shanklin seafront with a 5K low-tide run, finish-line sea dip and tickets listed at £15.

09:00–11:00 · Shanklin (Clock Tower) Beach · £15.00 · Booking required

English Heritage Great British Summer activities run at Carisbrooke Castle from 18 July into early September 2026.

Official event continues to 6 September. · Carisbrooke · Paid

English Heritage's Great British Summer runs at Osborne House in East Cowes daily from 18 July to 6 September, with fairground activities, circus skills, puppet antics and a children's stamp passport trail.

Official event continues to 6 September. · Osborne House · Paid

A collaborative morning workshop at Carisbrooke Flower Farm pairing an aromatherapy blend and wellbeing mist session with hand-picking seasonal blooms for a bespoke bouquet, tea, cake and a wellbeing gift included.

10:00–13:00 · Carisbrooke Flower Farm · £50.00 · Booking required

A real ale weekend with an extended evening train service at the Isle of Wight Steam Railway on 18 and 19 July 2026.

Bars open from 16:00; free station entry if not travelling. · Isle of Wight Steam Railway · Paid

Locally made craft and gift stalls inside the Isle of Wight Bus and Coach Museum hangar in Ryde, with café open.

11:00–16:00 · Isle of Wight Bus & Coach Museum

Sunday afternoon live music at The Waterfront, Totland Bay (Wham 69 on the poster). Music from 3pm; check venue for food service times. Source: venue poster / eatbythesea.com.

15:00–18:00 · The Waterfront

Sound bath in the arched interior of Bembridge Fort on Culver Down with views across the Solent.

17:00–19:00 · Bembridge Fort (Culver Down) · £20.00 · 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

Ventnor Fringe returns from 17 to 26 July 2026 with performances and events across Ventnor.

Programme times not found. · Ventnor Town Centre

The UK’s leading classic yacht regatta returns to Cowes with five days of IRC racing and harbour-side social events.

Racing and social programme varies by day. · Cowes (various locations)

English Heritage Great British Summer activities run at Carisbrooke Castle from 18 July into early September 2026.

Official event continues to 6 September. · Carisbrooke · Paid

English Heritage's Great British Summer runs at Osborne House in East Cowes daily from 18 July to 6 September, with fairground activities, circus skills, puppet antics and a children's stamp passport trail.

Official event continues to 6 September. · Osborne House · Paid

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

Ventnor Fringe returns from 17 to 26 July 2026 with performances and events across Ventnor.

Programme times not found. · Ventnor Town Centre

The UK’s leading classic yacht regatta returns to Cowes with five days of IRC racing and harbour-side social events.

Racing and social programme varies by day. · Cowes (various locations)

English Heritage Great British Summer activities run at Carisbrooke Castle from 18 July into early September 2026.

Official event continues to 6 September. · Carisbrooke · Paid

English Heritage's Great British Summer runs at Osborne House in East Cowes daily from 18 July to 6 September, with fairground activities, circus skills, puppet antics and a children's stamp passport trail.

Official event continues to 6 September. · Osborne House · Paid

Tuesday evening fish and chip events at the Isle of Wight Steam Railway through July and August 2026.

17:00–20:00 · Isle of Wight Steam Railway · £16.95 · Booking required

70 Girls 70 brings Kander and Ebb's offbeat musical comedy to Apollo Theatre in Newport, with performances from 17 to 25 July 2026.

Selected performance dates · Apollo Theatre · £5.00 · 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

Ventnor Fringe returns from 17 to 26 July 2026 with performances and events across Ventnor.

Programme times not found. · Ventnor Town Centre

The UK’s leading classic yacht regatta returns to Cowes with five days of IRC racing and harbour-side social events.

Racing and social programme varies by day. · Cowes (various locations)

English Heritage Great British Summer activities run at Carisbrooke Castle from 18 July into early September 2026.

Official event continues to 6 September. · Carisbrooke · Paid

English Heritage's Great British Summer runs at Osborne House in East Cowes daily from 18 July to 6 September, with fairground activities, circus skills, puppet antics and a children's stamp passport trail.

Official event continues to 6 September. · Osborne House · Paid

The Piano Cafe's July quiz night brings teams of two to six back to Freshwater for a Wednesday evening fundraiser.

19:00–21:30 · The Piano Cafe · Dogs welcome · Booking required

70 Girls 70 brings Kander and Ebb's offbeat musical comedy to Apollo Theatre in Newport, with performances from 17 to 25 July 2026.

Selected performance dates · Apollo Theatre · £5.00 · 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

Ventnor Fringe returns from 17 to 26 July 2026 with performances and events across Ventnor.

Programme times not found. · Ventnor Town Centre

The UK’s leading classic yacht regatta returns to Cowes with five days of IRC racing and harbour-side social events.

Racing and social programme varies by day. · Cowes (various locations)

Morning woodland retreat for new mothers at Haylands Farm with mindfulness, forest bathing and campfire brunch.

09:30–12:30 · Haylands Farm · £25.00 · Booking required

English Heritage Great British Summer activities run at Carisbrooke Castle from 18 July into early September 2026.

Official event continues to 6 September. · Carisbrooke · Paid

English Heritage's Great British Summer runs at Osborne House in East Cowes daily from 18 July to 6 September, with fairground activities, circus skills, puppet antics and a children's stamp passport trail.

Official event continues to 6 September. · Osborne House · Paid

The Apollo Theatre screens Mozart’s Le Nozze di Figaro from the Royal Opera House, conducted by Antonio Pappano.

19:00–22:30 · Apollo Theatre · £15.00 · Booking required

70 Girls 70 brings Kander and Ebb's offbeat musical comedy to Apollo Theatre in Newport, with performances from 17 to 25 July 2026.

Selected performance dates · Apollo Theatre · £5.00 · Booking required

A long-running Status Quo tribute at Shanklin Theatre with live band and more than twenty chart hits from the denim years.

19:30–22:00 · Shanklin Theatre · £30.00 · 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

Ventnor Fringe returns from 17 to 26 July 2026 with performances and events across Ventnor.

Programme times not found. · Ventnor Town Centre

The UK’s leading classic yacht regatta returns to Cowes with five days of IRC racing and harbour-side social events.

Racing and social programme varies by day. · Cowes (various locations)

English Heritage Great British Summer activities run at Carisbrooke Castle from 18 July into early September 2026.

Official event continues to 6 September. · Carisbrooke · Paid

English Heritage's Great British Summer runs at Osborne House in East Cowes daily from 18 July to 6 September, with fairground activities, circus skills, puppet antics and a children's stamp passport trail.

Official event continues to 6 September. · Osborne House · Paid

70 Girls 70 brings Kander and Ebb's offbeat musical comedy to Apollo Theatre in Newport, with performances from 17 to 25 July 2026.

Selected performance dates · Apollo Theatre · £5.00 · 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

Ventnor Fringe returns from 17 to 26 July 2026 with performances and events across Ventnor.

Programme times not found. · Ventnor Town Centre

An Isle of Wight Symphony Orchestra concert at the Isle of Wight Steam Railway on Saturday 25 July 2026.

Concert starts 15:00; end time not found. · Isle of Wight Steam Railway · £18.00 · Dogs welcome · Booking required

The UK’s leading classic yacht regatta returns to Cowes with five days of IRC racing and harbour-side social events.

Racing and social programme varies by day. · Cowes (various locations)

English Heritage Great British Summer activities run at Carisbrooke Castle from 18 July into early September 2026.

Official event continues to 6 September. · Carisbrooke · Paid

English Heritage's Great British Summer runs at Osborne House in East Cowes daily from 18 July to 6 September, with fairground activities, circus skills, puppet antics and a children's stamp passport trail.

Official event continues to 6 September. · Osborne House · Paid

A free-entry school summer fair in Sandown with tombola, raffle, stalls, games, dance, sweet treats, tea and cakes, raising funds for an island charity.

12:30–15:00 · The Bay Primary School · Free

Medina Community Choir performs Gospel Gold at St Mary's Church in Cowes before its Paris tour, with an award-winning choir in a summer Saturday setting.

19:00–21:30 · St Mary's Church, Cowes · £12.00 · Booking required

Sandown Main Carnival returns on Saturday 25 July at 7pm, with floats, bands and costumes moving through town from Sandown Library.

19:00–21:30 · Sandown Library · Free

A Lady Gaga tribute at Shanklin Theatre with Georgia Crandon, live band, dancers and the singer’s biggest hits.

19:30–22:00 · Shanklin Theatre · £30.00 · Booking required

70 Girls 70 brings Kander and Ebb's offbeat musical comedy to Apollo Theatre in Newport, with performances from 17 to 25 July 2026.

Selected performance dates · Apollo Theatre · £5.00 · Booking required

The Apollo Theatre in Newport screens The Rocky Horror Picture Show as an interactive evening where dressing up and props are part of the fun.

19:30–22:00 · Apollo Theatre · £10.00 · 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

Ventnor Fringe returns from 17 to 26 July 2026 with performances and events across Ventnor.

Programme times not found. · Ventnor Town Centre

English Heritage Great British Summer activities run at Carisbrooke Castle from 18 July into early September 2026.

Official event continues to 6 September. · Carisbrooke · Paid

English Heritage's Great British Summer runs at Osborne House in East Cowes daily from 18 July to 6 September, with fairground activities, circus skills, puppet antics and a children's stamp passport trail.

Official event continues to 6 September. · Osborne House · Paid

The Island Highland Gathering is in its 15th year at GG's in Newport on 26 July, with six pipe bands, Highland dancing, falconry, caber tossing, and Scottish food raising money for Aspire Ryde.

10:00–17:00 · GG's · Booking required

Sunday afternoon live music at The Waterfront, Totland Bay (Mumma Mia 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

Scallywags Fun Club opens five weeks of summer holiday sessions at Oakfield in Ryde for ages 3 to 18, with HAF free places for eligible families.

Ongoing · Scallywags Fun Club · Booking required

English Heritage Great British Summer activities run at Carisbrooke Castle from 18 July into early September 2026.

Official event continues to 6 September. · Carisbrooke · Paid

English Heritage's Great British Summer runs at Osborne House in East Cowes daily from 18 July to 6 September, with fairground activities, circus skills, puppet antics and a children's stamp passport trail.

Official event continues to 6 September. · Osborne House · Paid

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

Scallywags Fun Club opens five weeks of summer holiday sessions at Oakfield in Ryde for ages 3 to 18, with HAF free places for eligible families.

Ongoing · Scallywags Fun Club · Booking required

English Heritage Great British Summer activities run at Carisbrooke Castle from 18 July into early September 2026.

Official event continues to 6 September. · Carisbrooke · Paid

English Heritage's Great British Summer runs at Osborne House in East Cowes daily from 18 July to 6 September, with fairground activities, circus skills, puppet antics and a children's stamp passport trail.

Official event continues to 6 September. · Osborne House · Paid

Tuesday evening fish and chip events at the Isle of Wight Steam Railway through July and August 2026.

17:00–20:00 · Isle of Wight Steam Railway · £16.95 · 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

Scallywags Fun Club opens five weeks of summer holiday sessions at Oakfield in Ryde for ages 3 to 18, with HAF free places for eligible families.

Ongoing · Scallywags Fun Club · Booking required

English Heritage Great British Summer activities run at Carisbrooke Castle from 18 July into early September 2026.

Official event continues to 6 September. · Carisbrooke · Paid

English Heritage's Great British Summer runs at Osborne House in East Cowes daily from 18 July to 6 September, with fairground activities, circus skills, puppet antics and a children's stamp passport trail.

Official event continues to 6 September. · Osborne House · Paid

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

Scallywags Fun Club opens five weeks of summer holiday sessions at Oakfield in Ryde for ages 3 to 18, with HAF free places for eligible families.

Ongoing · Scallywags Fun Club · Booking required

English Heritage Great British Summer activities run at Carisbrooke Castle from 18 July into early September 2026.

Official event continues to 6 September. · Carisbrooke · Paid

English Heritage's Great British Summer runs at Osborne House in East Cowes daily from 18 July to 6 September, with fairground activities, circus skills, puppet antics and a children's stamp passport trail.

Official event continues to 6 September. · Osborne House · Paid

Stacy Green stars in a P!nk tribute at Shanklin Theatre with the Vertigo Band and the singer’s biggest arena anthems.

19:30–22:00 · Shanklin Theatre · £29.00 · 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

Scallywags Fun Club opens five weeks of summer holiday sessions at Oakfield in Ryde for ages 3 to 18, with HAF free places for eligible families.

Ongoing · Scallywags Fun Club · Booking required

English Heritage Great British Summer activities run at Carisbrooke Castle from 18 July into early September 2026.

Official event continues to 6 September. · Carisbrooke · Paid

English Heritage's Great British Summer runs at Osborne House in East Cowes daily from 18 July to 6 September, with fairground activities, circus skills, puppet antics and a children's stamp passport trail.

Official event continues to 6 September. · Osborne House · Paid

Wight Proms runs at Northwood House, Cowes, from 31 July to 9 August 2026.

Hooray for Hollywood; main show 19:30-21:30. · Northwood House · Paid · No dogs · Booking required

A caller-led barn dance at Bembridge Village Hall with live band, BYO drinks and proceeds for Home-Start Isle of Wight.

19:00–22:00 · Bembridge Village Hall · £12.50 · Booking required

Quantum Theatre brings Treasure Island to Ventnor Botanic Garden on Friday 31 July, with pirates, sea shanties, sword fights and outdoor family theatre.

19:00–20:40 · Ventnor Botanic Garden · Dogs welcome · 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

Scallywags Fun Club opens five weeks of summer holiday sessions at Oakfield in Ryde for ages 3 to 18, with HAF free places for eligible families.

Ongoing · Scallywags Fun Club · Booking required

Wight Proms runs at Northwood House, Cowes, from 31 July to 9 August 2026.

Specific listing not found in checked extract. · Northwood House · Paid · No dogs · Booking required

Cowes Week marks its bicentenary with racing from Saturday 1 to Friday 7 August 2026.

Daily race/spectator times not found. · Cowes (various locations)

Chale Show takes place at Chale Recreation Ground on Saturday 1 and Sunday 2 August 2026.

Daily 10:00-17:00 · Chale Recreation Ground · Paid · Dogs welcome

English Heritage Great British Summer activities run at Carisbrooke Castle from 18 July into early September 2026.

Official event continues to 6 September. · Carisbrooke · Paid

English Heritage's Great British Summer runs at Osborne House in East Cowes daily from 18 July to 6 September, with fairground activities, circus skills, puppet antics and a children's stamp passport trail.

Official event continues to 6 September. · Osborne House · Paid

The Chale Show brings arena acts, horticulture, live music, a vintage fairground and traditional country show activity to Chale Recreation Ground.

Programme varies by day · Chale Recreation Ground · Paid

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

Scallywags Fun Club opens five weeks of summer holiday sessions at Oakfield in Ryde for ages 3 to 18, with HAF free places for eligible families.

Ongoing · Scallywags Fun Club · Booking required

Cowes Week marks its bicentenary with racing from Saturday 1 to Friday 7 August 2026.

Daily race/spectator times not found. · Cowes (various locations)

Chale Show takes place at Chale Recreation Ground on Saturday 1 and Sunday 2 August 2026.

Daily 10:00-17:00 · Chale Recreation Ground · Paid · Dogs welcome

English Heritage Great British Summer activities run at Carisbrooke Castle from 18 July into early September 2026.

Official event continues to 6 September. · Carisbrooke · Paid

English Heritage's Great British Summer runs at Osborne House in East Cowes daily from 18 July to 6 September, with fairground activities, circus skills, puppet antics and a children's stamp passport trail.

Official event continues to 6 September. · Osborne House · Paid

The Chale Show brings arena acts, horticulture, live music, a vintage fairground and traditional country show activity to Chale Recreation Ground.

Programme varies by day · Chale Recreation Ground · Paid

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

15:00–18:00 · The Waterfront

Wight Proms runs at Northwood House, Cowes, from 31 July to 9 August 2026.

Jasper Carrott with Strictly ABBA. · Northwood House · Paid · No dogs · 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

Scallywags Fun Club opens five weeks of summer holiday sessions at Oakfield in Ryde for ages 3 to 18, with HAF free places for eligible families.

Ongoing · Scallywags Fun Club · Booking required

Wight Proms runs at Northwood House, Cowes, from 31 July to 9 August 2026.

Specific listing not found in checked extract. · Northwood House · Paid · No dogs · Booking required

Cowes Week marks its bicentenary with racing from Saturday 1 to Friday 7 August 2026.

Daily race/spectator times not found. · Cowes (various locations)

English Heritage Great British Summer activities run at Carisbrooke Castle from 18 July into early September 2026.

Official event continues to 6 September. · Carisbrooke · Paid

English Heritage's Great British Summer runs at Osborne House in East Cowes daily from 18 July to 6 September, with fairground activities, circus skills, puppet antics and a children's stamp passport trail.

Official event continues to 6 September. · Osborne House · Paid

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

Scallywags Fun Club opens five weeks of summer holiday sessions at Oakfield in Ryde for ages 3 to 18, with HAF free places for eligible families.

Ongoing · Scallywags Fun Club · Booking required

Wight Proms runs at Northwood House, Cowes, from 31 July to 9 August 2026.

Specific listing not found in checked extract. · Northwood House · Paid · No dogs · Booking required

Cowes Week marks its bicentenary with racing from Saturday 1 to Friday 7 August 2026.

Daily race/spectator times not found. · Cowes (various locations)

English Heritage Great British Summer activities run at Carisbrooke Castle from 18 July into early September 2026.

Official event continues to 6 September. · Carisbrooke · Paid

English Heritage's Great British Summer runs at Osborne House in East Cowes daily from 18 July to 6 September, with fairground activities, circus skills, puppet antics and a children's stamp passport trail.

Official event continues to 6 September. · Osborne House · Paid

Tuesday evening fish and chip events at the Isle of Wight Steam Railway through July and August 2026.

17:00–20:00 · Isle of Wight Steam Railway · £16.95 · Booking required