Challenging rides on the Isle of Wight for expert cyclists looking to escape the city

The Isle of Wight is known for being a challenging but beautiful place to ride a bicycle.

The unique geology of the island has left its landscape with a profile full of constantly undulating, and sometimes cliff-like, climbs. Add the Atlantic headwinds to the mix and you are sure to get a good workout wherever you ride on the Island.

In this feature, Isle of Wight endurance cyclist Tim Wiggins provides insight into two of his favourite training loops on the Island. Both starting and finishing from Ryde (the arrival point of the Wightlink FastCat passenger service), these expert-level tours will leave you with legs very ready for a sit down on the ferry journey home.

At 80 miles (133 kilometres), the ‘Points and Peaks’ tour is a tough day in the saddle.

Starting from Ryde, you head straight out over the Downs, southbound towards the coastal town of Ventnor. Some short steep climbs await you in Newchurch and Wroxall, before you roll down the steep switchbacks into Ventnor.

If you are looking for an early stopover, the Ventnor Botanic Gardens’ Plantation Room Café serve a superb coffee at mile marker 14.

From Ventnor, you head along the now traffic-free Undercliff Road, through to Niton. Then it is up the hard climb all the way over the Blackgang Road pass.

Back-roads from Blackgang will take you to Shorwell, up the steep Shorwell Shute climb, and down the long descent into Carisbrooke. Don’t relax though, because the climb ramps up again onto the Middle Road, as you turn westwards towards Freshwater.

Carisbrooke to Calbourne, and Calbourne to Mottistone. Do not be fooled by the name ‘Strawberry Lane’ – the climb is a tough ascent through Brighstone Forest.

Stop off at ‘The Sun Inn’ at Hulverstone for refreshments at the 35-mile point.

From Hulverstone you head through to Yarmouth – another Wightlink port, with regular ferries to Lymington. There are a selection of great cafés and bakeries in the town for refreshments.

Don’t weigh yourself down with too much cake though; as out of Yarmouth it is a long climb all the way up to the furthest western point on the Island – the Needles Battery. Spectacular views await you at the summit.

From The Needles, you head through to Freshwater Bay, then hit the famous and stunning Military Road. Settle into a good rhythm, and you will see miles 50 to 60 fly by…

Then, you reach Blackgang… (again!). This time from the west side, the climb is shorter and steeper than the ascent earlier in the day. Make sure you have taken on some refreshments before you get stuck in.

From Blackgang, you coast down to Whitwell and then through to Chale Green. Chale Green Stores have a fantastic cake selection, if you decide you need a treat after your efforts.

From Chale Green, it is an undulating ride back to Ryde; over Chillerton, and through to Newport, before heading back over the Downs on Burnt House Lane.

By the time you get back to Ryde, you are sure to feel like you have put in some hard graft. Ice cream or fish and chips on the seafront are highly recommended.

This second route takes on some of the less well-known climbs on the Isle of Wight; secret leg burners, which will have you reaching for your lowest gear.

The route starts out fairly moderately, following the Round The Island route out of Ryde and through St Helens and Bembridge. From there, you continue through to Alverstone, and the hills begin properly.

The climbs out of Alverstone and into Newchurch will warm up your legs, but the real hard graft begins at mile 19, when you reach the base of Cowlease Hill in Shanklin. Enjoy the coastal views as you climb, and follow the road all the way through to Ventnor.

Call into Ventnor Botanic Gardens or Ventnor Winter Gardens for refreshments at around mile 24 – you will need it for what comes next…

Along the Undercliff, you take a sharp switchback, and climb the singletrack STEEP road up Seven Sisters.  If this gradient doesn’t have you out of the saddle, it will be a surprise.

Once onto the Whitwell road you keep climbing up to Niton, and then up and over Blackgang Road. Descending down into Chale Green, it is worth calling into Chale Green Stores if you are looking for refreshments.

From Chale to Chillerton, and then inland towards the centre of the Island. Turning at Carisbrooke (a sizable town with local shops), you head back out west towards Shorwell.

The climb out of Brighstone could take you by surprise, and is another tough gradient to conquer. You then do a small loop through Newbridge and Wellow; you can stop off at West Wight Alpacas & Llamas for some great coffee and cake.

From Freshwater you head up the climb from the bay, and witness the panoramic views of Military Road. Following the back lanes eastwards you eventually come to Blackgang road climb for the second time on this route. It is shorter and steeper from the west side, so you are sure to feel the effort.

From Blackgang, through Niton (perhaps stop at the Buddle Inn for a drink or lunch), then you continue along the Undercliff road and… back up Seven Sisters for a second time!

Thankfully, that is the worst of the climbing done for the day; you head through to Ventnor, and then make your way through Wroxall, Newchurch and Rowlands Lane, back to your finish point at Ryde.

At 85 miles, and a whole load of climbing (1,800+ metres), this route will leave you assured that the Isle of Wight is a tough place to ride a bike.