Next 30 days on the Isle of Wight

Castle to Crown sets out from Carisbrooke High Street car park for a free four-hour heritage walk on Thursday 8 October.

10:00–14:00 · Carisbrooke · Free · Booking required

Walk 3.5 miles through Bowcombe Valley from Carisbrooke Priory, tracing Roman settlement beside the Lukely Brook on 8 October.

10:30–12:30 · Carisbrooke · £6.00 · Booking required

The Isle of Wight Literary Festival opens in Cowes with talks, food writing and an evening Fizz Quiz.

13:30–21:30 · Cowes (various locations) · 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

Friday’s Isle of Wight Literary Festival programme in Cowes includes Robert Hardman, A N Wilson, Jill Dougherty and Penny Junor.

Starts 11:00; finish not advertised · Cowes (various locations) · Booking required

The Great Nurdle Exhibition turns tiny plastic pellets and their harm to Island shorelines into close-up art at Quay Arts.

Daily 09:00-16:00 · Quay Arts · Free

Ryde Art Collective fills Quay Arts’ West Gallery with work by Island artists from 26 September to 8 November.

Closed 24 October. · Quay Arts · Free

Local stories lead a two-and-a-half-hour walk from the Isle of Wight Heritage Resource Centre into Northwood Cemetery on 9 October.

10:30–13:00 · Cowes (various locations) · Donations welcome · Booking required

A low-cost Halloween afternoon dance at East Cowes Town Hall, with optional fancy dress, tea, cakes and prizes.

14:00–16:00 · East Cowes Town Hall · £2.00

GG’s starts its Oktoberfest weekend with German-style food, drink and live entertainment on Friday 9 October from 18:00.

18:00–23:00 · GG's · £10.00 · Booking required

Quivers bring an evening of comedy and entertainment to Ryde Castle Hotel. Tickets cost £10 through hotel reception.

19:00–23:00 · Ryde Castle Hotel · £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

Saturday’s Cowes festival sessions include Ann Cleeves, Clare Balding, Stephen Sackur, Chris Galvin and Eric Lanlard.

Starts 10:30; finish not advertised · Cowes (various locations) · Booking required

Historian Tim Wander explores the Anglo-Zulu War at Bembridge Fort, with original weapons and film excerpts. Tickets are £10 plus fee.

Starts 14:00; finish not advertised · Bembridge Fort (Culver Down) · £10.00 · Booking required

The Great Nurdle Exhibition turns tiny plastic pellets and their harm to Island shorelines into close-up art at Quay Arts.

Daily 09:00-16:00 · Quay Arts · Free

Ryde Art Collective fills Quay Arts’ West Gallery with work by Island artists from 26 September to 8 November.

Closed 24 October. · Quay Arts · Free

Newport Roman Walk leaves the Roman Villa for a 90-minute exploration of the town’s wider Roman story on 10 October.

10:00–11:30 · Newport · £6.00 · Booking required

Beer & Steam opens at Havenstreet with real ales, cider and a 2 Bit live set. Festival entry is free; trains cost extra.

11:00–17:00 · Isle of Wight Steam Railway · Free

Browse local makers at Brading Youth & Community Centre’s Saturday craft bazaar, with a café open during the event.

11:00–15:00 · Brading Youth & Community Centre

Saturday brings a second five-hour Oktoberfest evening to GG’s, combining German-style food, drinks and live entertainment from 18:00.

18:00–23:00 · GG's · £10.00 · Booking required

A free evening for 18 to 35-year-olds at Calbourne Water Mill, combining a bat walk, fire pit and time with the Biosphere community.

19:00–21:00 · Calbourne Water Mill · Free · Dogs welcome · Booking required

Join D.A.W. Paranormal for an adults-only after-dark investigation at Dimbola Museum & Galleries in Freshwater Bay.

19:30–00:00 · Dimbola Museum & Galleries · £40.00 · 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

Altitude Church’s free Autumnfest in Sandown includes inflatables, autumn crafts, games and lunch.

Starts 10:30; finish not advertised · The Bay Secondary School · Free

The literary festival closes in Cowes with Sunday talks featuring Mary Portas, Hugo Burnand, Ben Robinson and Clive Tyldesley.

Starts 10:30; finish not advertised · Cowes (various locations) · Booking required

Ryde Art Collective fills Quay Arts’ West Gallery with work by Island artists from 26 September to 8 November.

Closed 24 October. · Quay Arts · Free

Learn beginner-friendly Kinusaiga textile art at Jubilee Stores in Newport, using fabric scraps to create a landscape across two Sunday workshop sessions.

10:00–15:00 · Jubilee Stores · £85.00 · Booking required New

A free seven-hour gravel ride leaves Ryde Esplanade for Island tracks and lanes on Sunday 11 October, with booking required.

10:00–17:00 · Ryde · Free · Booking required

Sunday at Beer & Steam has real ales, cider and music from JC & Angelina at Havenstreet. Festival entry is free.

11:00–17:00 · Isle of Wight Steam Railway · Free

Follow Charles Dickens through Bonchurch on a two-and-a-half-hour literary walk beginning at the village pond on Sunday 11 October.

14:00–16:30 · Bonchurch · £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

Ryde Art Collective fills Quay Arts’ West Gallery with work by Island artists from 26 September to 8 November.

Closed 24 October. · Quay Arts · 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

Ryde Art Collective fills Quay Arts’ West Gallery with work by Island artists from 26 September to 8 November.

Closed 24 October. · Quay Arts · Free

A £6 community lunch at East Cowes Town Hall, including a meal, tea or coffee and gluten-free options.

12:00–14:30 · East Cowes Town Hall · £6.00 · Booking required

Blue Orbits, formerly Triangulum, play an intimate two-hour set at Sounds + Grounds in Cowes, with doors opening at 6.30pm.

19:00–21:00 · Sounds + Grounds · £16.00 · 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

Ryde Art Collective fills Quay Arts’ West Gallery with work by Island artists from 26 September to 8 November.

Closed 24 October. · Quay Arts · Free

Teams of up to five face Halloween questions and compete for prizes at Waterstones Newport on Wednesday 14 October.

18:00–19:30 · Newport · £3.00 · Booking required

A Wednesday open-mic evening hosted by Sebotage at Ventnor Royal British Legion Social Club, running from 7.30pm to 10pm.

19:30–22:00 · Royal British Legion Social Club Ventnor

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

Ryde Art Collective fills Quay Arts’ West Gallery with work by Island artists from 26 September to 8 November.

Closed 24 October. · Quay Arts · 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

Ryde Art Collective fills Quay Arts’ West Gallery with work by Island artists from 26 September to 8 November.

Closed 24 October. · Quay Arts · 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

Half-term magic at Isle of Wight Steam Railway includes wizard school, shows, crafts, trails and a spooky train from 17 to 31 October.

Daily hours vary; check railway programme · Isle of Wight Steam Railway · Free

Ryde Art Collective fills Quay Arts’ West Gallery with work by Island artists from 26 September to 8 November.

Closed 24 October. · Quay Arts · Free

An informal afternoon catch-up for people living with chronic illness at Town Choice Café Bar in Newport.

14:00–16:00 · Town Choice Café Bar · Free

Local performers transform into familiar music stars for a charity show at Newport’s Riverside Centre on Saturday 17 October.

19:30–23:00 · Newport · £11.55 · Booking required

Fruitylicious starts its Pavilion party in Ryde at 20:00 on Saturday 17 October, with the night continuing past midnight.

20:00–23:59 · Ryde · 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 Fruitylicious party at The Pavilion carries on from midnight to 01:00 on Sunday 18 October after a Saturday-night start.

00:00–01:00 · Ryde · Booking required

Try free fitness classes and weightlifting at Velocity Fitness Gym’s Sandown open day. Class booking is advised.

Starts 09:00; finish not advertised · Velocity Fitness Gym · Free

Half-term magic at Isle of Wight Steam Railway includes wizard school, shows, crafts, trails and a spooky train from 17 to 31 October.

Daily hours vary; check railway programme · Isle of Wight Steam Railway · Free

Ryde Art Collective fills Quay Arts’ West Gallery with work by Island artists from 26 September to 8 November.

Closed 24 October. · Quay Arts · Free

Learn beginner-friendly Kinusaiga textile art at Jubilee Stores in Newport, using fabric scraps to create a landscape across two Sunday workshop sessions.

10:00–15:00 · Jubilee Stores · £85.00 · Booking required New

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

Half-term magic at Isle of Wight Steam Railway includes wizard school, shows, crafts, trails and a spooky train from 17 to 31 October.

Daily hours vary; check railway programme · Isle of Wight Steam Railway · Free

Ryde Art Collective fills Quay Arts’ West Gallery with work by Island artists from 26 September to 8 November.

Closed 24 October. · Quay Arts · Free

A beginner-friendly morning of Halloween pottery in Freshwater, with wheel work, painting and spooky clay creations for adults and children.

10:00–12:00 · Isle of Wight Pottery · £27.50 · Booking required

An afternoon Halloween clay session at Isle of Wight Pottery, open to beginners, adults and children with glazing and firing included.

14:00–16:00 · Isle of Wight Pottery · £27.50 · 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

Half-term magic at Isle of Wight Steam Railway includes wizard school, shows, crafts, trails and a spooky train from 17 to 31 October.

Daily hours vary; check railway programme · Isle of Wight Steam Railway · Free

Ryde Art Collective fills Quay Arts’ West Gallery with work by Island artists from 26 September to 8 November.

Closed 24 October. · Quay Arts · Free

Join Steve and Ella Baxter at Quay Arts in Newport for a free family drawing drop-in, making a shared plant-inspired artwork with all materials supplied.

10:00–13:00 · Quay Arts · Free New

Conn Artists Theatre brings Charlotte Brontë’s Jane Eyre to Quay Arts in Newport, with five actors, original music and a new staging directed by Nick Young.

19:30–22:00 · Quay Arts · £21.00 · Booking required New

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

Half-term magic at Isle of Wight Steam Railway includes wizard school, shows, crafts, trails and a spooky train from 17 to 31 October.

Daily hours vary; check railway programme · Isle of Wight Steam Railway · Free

Ryde Art Collective fills Quay Arts’ West Gallery with work by Island artists from 26 September to 8 November.

Closed 24 October. · Quay Arts · 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

Half-term magic at Isle of Wight Steam Railway includes wizard school, shows, crafts, trails and a spooky train from 17 to 31 October.

Daily hours vary; check railway programme · Isle of Wight Steam Railway · Free

Ryde Art Collective fills Quay Arts’ West Gallery with work by Island artists from 26 September to 8 November.

Closed 24 October. · Quay Arts · Free

Try playing the harp with Fran Barsby at Ryde Methodist Church, an hour-long Harp on Wight workshop with instruments supplied and all ages welcome.

14:00–15:00 · Ryde Methodist Church · £10.00 · Booking required New

Radiator Rick Asherson teaches a one-hour blues harmonica workshop at Ventnor Arts Club on 22 October, open to beginners aged seven and over.

19:30–20:30 · Ventnor Arts Club · £11.25 · 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

Half-term magic at Isle of Wight Steam Railway includes wizard school, shows, crafts, trails and a spooky train from 17 to 31 October.

Daily hours vary; check railway programme · Isle of Wight Steam Railway · Free

Ryde Art Collective fills Quay Arts’ West Gallery with work by Island artists from 26 September to 8 November.

Closed 24 October. · Quay Arts · Free

Drag performance and a late party take over Strings Bar & Venue for an adults-only Newport night on Friday 23 October.

19:00–23:59 · 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

Half-term magic at Isle of Wight Steam Railway includes wizard school, shows, crafts, trails and a spooky train from 17 to 31 October.

Daily hours vary; check railway programme · Isle of Wight Steam Railway · 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

Half-term magic at Isle of Wight Steam Railway includes wizard school, shows, crafts, trails and a spooky train from 17 to 31 October.

Daily hours vary; check railway programme · Isle of Wight Steam Railway · Free

Ryde Art Collective fills Quay Arts’ West Gallery with work by Island artists from 26 September to 8 November.

Closed 24 October. · Quay Arts · Free

Meet makers and browse creative supplies at The Bees Needles in Northwood House, Cowes, with free entry, demonstrations, talks and an indoor artisan shopping area.

10:30–15:00 · Northwood House · Free New

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

Half-term magic at Isle of Wight Steam Railway includes wizard school, shows, crafts, trails and a spooky train from 17 to 31 October.

Daily hours vary; check railway programme · Isle of Wight Steam Railway · Free

Ryde Art Collective fills Quay Arts’ West Gallery with work by Island artists from 26 September to 8 November.

Closed 24 October. · Quay Arts · Free

Waterstones Newport counts down to ACOTAR 6 with quizzes, activities and prizes from 21:30 on Monday 26 October.

21:30–23:59 · Newport · £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

Collect ACOTAR 6 at Waterstones Newport just after midnight on Tuesday 27 October, following the previous evening’s fan party.

00:00–00:30 · Newport · £5.00 · Booking required

Half-term magic at Isle of Wight Steam Railway includes wizard school, shows, crafts, trails and a spooky train from 17 to 31 October.

Daily hours vary; check railway programme · Isle of Wight Steam Railway · Free

Ryde Art Collective fills Quay Arts’ West Gallery with work by Island artists from 26 September to 8 November.

Closed 24 October. · Quay Arts · 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

Half-term magic at Isle of Wight Steam Railway includes wizard school, shows, crafts, trails and a spooky train from 17 to 31 October.

Daily hours vary; check railway programme · Isle of Wight Steam Railway · Free

Ryde Art Collective fills Quay Arts’ West Gallery with work by Island artists from 26 September to 8 November.

Closed 24 October. · Quay Arts · Free

Follow a Halloween woodland trail at Robin Hill in Downend, then join the family party tent for games, dancing, pumpkin painting and an evening drone show.

17:00–21:00 · Robin Hill · £16.99 · Booking required New

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

Half-term magic at Isle of Wight Steam Railway includes wizard school, shows, crafts, trails and a spooky train from 17 to 31 October.

Daily hours vary; check railway programme · Isle of Wight Steam Railway · Free

Ryde Art Collective fills Quay Arts’ West Gallery with work by Island artists from 26 September to 8 November.

Closed 24 October. · Quay Arts · Free

Follow a Halloween woodland trail at Robin Hill in Downend, then join the family party tent for games, dancing, pumpkin painting and an evening drone show.

17:00–21:00 · Robin Hill · £16.99 · Booking required New

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

Half-term magic at Isle of Wight Steam Railway includes wizard school, shows, crafts, trails and a spooky train from 17 to 31 October.

Daily hours vary; check railway programme · Isle of Wight Steam Railway · Free

Ryde Art Collective fills Quay Arts’ West Gallery with work by Island artists from 26 September to 8 November.

Closed 24 October. · Quay Arts · Free

Follow a Halloween woodland trail at Robin Hill in Downend, then join the family party tent for games, dancing, pumpkin painting and an evening drone show.

17:00–21:00 · Robin Hill · £16.99 · Booking required New

Halloween Boogie Bingo mixes DJ tracks, singalongs, games and prizes at GG’s, with fancy dress encouraged on Friday 30 October.

19:00–22:30 · GG's · £12.50 · Booking required

Half-term magic at Isle of Wight Steam Railway includes wizard school, shows, crafts, trails and a spooky train from 17 to 31 October.

Daily hours vary; check railway programme · Isle of Wight Steam Railway · Free

Ryde Art Collective fills Quay Arts’ West Gallery with work by Island artists from 26 September to 8 November.

Closed 24 October. · Quay Arts · Free

Mr Sleepybum’s Dream Machine brings interactive sketches and slapstick to Quay Arts in Newport, with an hour of theatre for children aged three to eight.

14:00–15:00 · Quay Arts · £10.50 · Booking required New

Ryde Art Collective fills Quay Arts’ West Gallery with work by Island artists from 26 September to 8 November.

Closed 24 October. · Quay Arts · Free

Ryde Art Collective fills Quay Arts’ West Gallery with work by Island artists from 26 September to 8 November.

Closed 24 October. · Quay Arts · Free

Ryde Art Collective fills Quay Arts’ West Gallery with work by Island artists from 26 September to 8 November.

Closed 24 October. · Quay Arts · Free

Ryde Art Collective fills Quay Arts’ West Gallery with work by Island artists from 26 September to 8 November.

Closed 24 October. · Quay Arts · Free

Ryde Art Collective fills Quay Arts’ West Gallery with work by Island artists from 26 September to 8 November.

Closed 24 October. · Quay Arts · Free

Ryde Art Collective fills Quay Arts’ West Gallery with work by Island artists from 26 September to 8 November.

Closed 24 October. · Quay Arts · Free