Things to do on the Isle of Wight in September

A September break to the Isle of Wight offers a great escape from routine. Not only is the weather mild, but with schools back in session you can enjoy a bit of sunshine and snag a deal.

In this blog, we explore the best things to do in September, from indulging in local cuisine and celebrating all things Steampunk to enjoying our dark skies. Join us as we uncover the perfect blend of relaxation and adventure that makes September an ideal time to experience the Isle of Wight’s charm and beauty.

At the Isle of Wight Steam Railway there’s a fantastic Cider and Cheese Festival on 6 and 7 September 2025 – and it’s free to enter! You’ll be able to sample your choice of 30 ciders and a huge variety of cheeses. If you can’t decide on just one cheese there are platters to pick with crunchy pickles and crackers which are washed down perfectly with a pint of cider – it’s the perfect way to while away an early autumn afternoon. There’s live music on both days and if you choose board the steam train, usual operating day fares apply.

The Isle of Wight has some of the darkest skies in the UK (where there are low levels of light pollution). Some of the best locations are found on the South Western Coast of the Isle of Wight along the Military Road. However, there are places all across the Island that can boast dark skies.

Enjoy dark skies on a clear night when the sun has completely set and there is no moonlight. Make sure you take something to lie on (a blanket or camping mat will do) along with food, drink and warm clothes. Pack a star-spotter guide and compass to help you find things.

Whether you’re a VW enthusiast, music lover, or just looking for a fun weekend away, Wight Buggin’ is a great place to be this September. It’s the Isle of Wight’s favourite VW and camping festival, set in the gorgeous surroundings of Retro Staycations – taking place this year on 12 to 14 September. Expect throwback discos, live bands, vehicle displays, unique stalls and delicious local food.

Here at Wightlink we’re busy carrying lots of delicious Isle of Wight sweetcorn to the mainland in the late summer.

Sweetcorn thrives in the Island’s fertile soil, benefiting from the region’s mild climate and abundant sunshine. Local farms cultivate this golden crop with care, resulting in sweet, tender kernels that are a highlight of summer harvests. Freshly picked sweetcorn from the Isle of Wight is celebrated for its rich flavor and juicy crunch, often enjoyed at local markets, food festivals, and in delicious seasonal dishes.

So, while you’re on the Island in September, make sure you pop into a local farm shop to enjoy it fresh from the fields – great if you’re staying in self-catering accommodation. Try your corn smothered in oak smoked garlic butter from The Garlic Farm, it’s a delicious combination!

Jazz fans should not miss the Isle of Wight’s only Jazz Festival in Newport this month. Taking place at various venues in the town from 24 to 28 September 2025 it’ll feature a diverse range of great musicians, including a few household names.  Expect an enchanting celebration of a genre that is both soulful and spontaneous, so whether you’re a newcomer or a seasoned jazz festival goer you’ll be able to connect in the shared joy of the music.

The Isle of Wight Steampunk Festival comes to Ryde again from 26 to 28 September 2025. This exciting festival will captivate attendees with a stellar line-up of performances, elaborate fashion displays, and unique stalls offering alternative gifts.

Highlights include a full day of free entertainment at Eastern Garden, teapot racing, a tea duelling competition, and evening concerts featuring renowned steampunk bands. Friday’s activities will feature steampunk goth entertainment and maritime sea shanties, while Saturday’s gala concert promises a grand finale. Attendees can enjoy the elegant Top Hat and Corset Dinner and participate in a grand promenade parade on Sunday, showcasing the vibrant steampunk spirit.

The Isle of Wight Bus & Coach Museum and the Wight Aviation Museum have joined forces for Modelfest, a fascinating model show that’ll take visitors through the evolution of transportation.  Over the weekend of 13 and 14 September, Modelfest will feature meticulously crafted models of iconic vehicles, infrastructures, and transport systems from different eras, giving a deep dive into how engineering and design shaped transportation over centuries.

There’ll be a complementary shuttle service, using vintage buses, every hour between the two museums and it’s free to enter both sites.