Carisbrooke Castle on the Isle of Wight from the air

Bringing history to life

From Victorian forts to monastic ruins and Bronze Age mounds to hilltop castles, the Isle of Wight is up to its elbows in history – boasting the UK’s oldest pier and one of the country’s earliest surviving phone boxes!

It’s the perfect destination for all things historical, geological and archaeological, whether you fancy joining druids for the summer solstice at the prehistoric Longstone or meeting the donkeys that turn the wheel of a 16th century well.

A man in Medieval costume riding a horse at a joust at Carisbrooke Castle, Isle of Wight

Whilst there are enough historical hotspots to fill an age or an epoch, we’re about to take you on a two-day trip around some of our favourites, so pack your travelling chest and straighten up that bowler hat as you step back in time at our award-winning Isle of Wight attractions.

First things first, it’s time to polish up that chain mail and gallop over to Carisbrooke Castle for this summer’s Legendary Joust, taking place 2–4 August. Watch as rival knights charge toward each other at full speed in the ultimate display of chivalry and honour. Expect shimmering armour, shattering lances and an abundance of thundering hooves.

Also not to be missed is the Knight’s Tournament, on 9–11 and 16–18 August – which aside from gallant warriors clashing swords in a Grand Melee – comes with a mediaeval encampment, where you can meet and greet people from the Middle Ages and watch them cook, craft and repair their weapons.

A family on a platform of the Isle of Wight Steam railway next to a steam train

Next, it’s time to let off some steam (quite literally), at the Isle of Wight Steam Railway. Step aboard at Havenstreet and make yourself comfy in a painstakingly restored Victorian carriage, complete with shimmering brass fittings and nostalgic sooty smells. As the conductor’s whistle sounds and the train begins chugging towards Wootton, keep an eye out the window for red squirrels and woodpeckers whilst the track wends its way through swathes of ancient woodland.

A couple walking in the gardens of The Swiss Cottage, Osborne, Isle of Wight

For some Isle of Wight history with an international twist, head to Osborne – once Queen Victoria’s palace by the sea (designed in an Italian style, by her German husband). Explore the underground kitchens where South Asian chefs prepared the Queen’s favourite chicken curry, stroll down to the Swiss Cottage where the young princes and princesses once played and then skim stones on the beach – just like the Russian Tsar’s children did on a visit in 1909.

Lounge at Quarr Abbey Farmhouse holiday let

As the sun sets and the summer night draws in, the historical experiences don’t have to end – with plenty of characterful cottages and comfy four-posters to spend the night in. Unusual options include the former stables of the poet Tennyson, located on the green and undulating Farringford Estate at Freshwater. You could also opt for a historic golf course clubhouse at St. Helens (now a National Trust holiday let) or a Grade II listed farmhouse set alongside the crumbling ruins of the original Quarr Abbey (dismantled by Henry VIII in the 1530s).

If there’s space in the diary (and you need an excuse to slip that astronaut helmet on again), start day two by setting coordinates for High Down Rocket Test Site, near Alum Bay. Originally a secret, this coastal concrete facility saw the launch of numerous test missiles and rockets during the height of the Cold War, with teams of operators directing the action from bunkers dug deep into the chalk cliffs below. Not only a must-visit for aerospace aficionados, the site also offers the most spectacular view of The Needles rocks and lighthouse – an unmissable seaside selfie for any Isle of Wight visit.

Next, why not put the wind in your sails – with a trip to the Island’s last surviving windmill. Standing on the edge of Bembridge village since the early 1700s, it ground corn into flour for generations of hungry locals, before becoming a Home Guard lookout post in the Second World War, and finally being saved from dereliction by villagers in the 1950s. Today, you can climb to the top of the fully restored mill, touch the three-hundred-year-old machinery and even get those muscles pumping as you try your hand at grinding flour yourself.

An illuminated bridge and gorge at Shanklin Chine

Rounding off this tour of historical hotspots is an evening excursion to the Island’s oldest attraction – Shanklin Chine. Once a hiding place for local smugglers, this stunning tree-lined gorge has been visited by Keats, Dickens and even Jane Austen since first opening its gates in 1817! As darkness falls, it takes on a mystical aura, as ‘the wondrous Chine’ is transformed with hundreds of coloured lights illuminating its paths, streams and waterfalls, adding a goosebump-inducing atmosphere to this already magical must-see destination.


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