Next 7 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

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

An immersive promenade performance through Bonchurch following the life and work of Victorian poet Algernon Swinburne.

10:30–12:00 · St Boniface Old Church · £11.55 · Booking required

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 Newport Quay fundraiser where teams pull an 18-tonne fire appliance, with live music, stalls, food and children’s entertainment.

10:00–17:30 · Newport · Free

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

Get On Stage host a family summer fayre at Newport C of E Primary School with live entertainment, stalls, BBQ, bouncy castle and raffles.

11:00–15:00 · Newport Church of England Primary School

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

Sunday afternoon social tango at Mushi At The Rex in Ventnor, with traditional Argentine music and room to dance or watch with a drink.

15:00–17:00 · Mushi At The Rex

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