5 Best Road Cycling Routes on the Isle of Wight

Road Cycling Routes Isle of Wight TW
Those that have ridden a road bike on the Isle of Wight will know that it is an incredible landscape to explore. The unique geology of the island has created a topographic profile that is undeniably tough, but unquestionably beautiful; from towering cliffs to wild wind-swept flats.

In this post, I have selected five of my favourite road cycling routes on the Isle of Wight—an insider's choice for the best road cycling on offer, as well as my personal recommendations for café stops and highlights.

Wight Road Route #1 – Panoramas and Pottery

  • Difficulty – Medium
  • Distance – 50 kilometres (31 miles)
  • Elevation Profile – Moderate (400 metres elevation gain)
We start with a fairly easy route in the West Wight—starting and finishing at the wonderful Caffe Isola in the centre of Newport, the ideal place for a pre-ride breakfast and coffee.

The route then heads out of town through the rolling hills of Bowcombe and down to Chale Green—a picturesque village at the southern point of the Island.

From here, you get to experience a little section of the famous Military Road, before heading inland through the lanes to Brighstone and Brook. You head up and over the climb of Brook Shute and then you can enjoy a much deserved coffee stop at the fantastic Chessell Pottery Cafe.

You roll down the panoramic Broad Lane to Thorley and then skirt through the estuary of Newtown Creek before heading back into Newport. This is a circular route full of magnificent views and highlights.

Tim Wiggins Best Road Cycling Routes on the Isle of Wight

Wight Road Route #2 – West Wight Wonder

  • Difficulty – Medium
  • Distance – 57 kilometres (35 miles)
  • Elevation Profile – Moderate (600 metres elevation gain)
This second route is of a similar difficulty to the first, but starts and finishes in the town of Yarmouth—a great starting point for an exploration of the western Isle of Wight.

The route heads out through the small village of Thorley and up Broad Lane—one of my favourite roads on the Island. You climb over Brook Shute and then turn east through Brighstone and Shorwell.

When you arrive at Chale Green you take on the challenging climb of Blackgang—a long ascent by UK standards, but with breathtaking views out over the Island at the summit.

A quick loop takes you down through the village of Niton, where there is a great village stores if you need to restock on local produce to fuel the ride. Then, you go back through Chale before joining the Military Road on a northwest course.

Enjoy the spectacular views along the Military Road—there is a reason this has been labelled as one of the most scenic roads in Europe. Then, treat yourself to an ice cream at the van at Compton Bay. It is the opportune re-fuelling stop, as the road gets quite undulating as you head towards Freshwater Bay from Compton; again though the views (photo below) are true Isle of Wight classics.

From Freshwater Bay it is a short but rolling road back to the finish of the tour at Yarmouth.

Tim Wiggins Best Road Cycling Routes on the Isle of Wight

Wight Road Route #3 – All of the Hills

  • Difficulty – Hard
  • Distance – 135 kilometres (82 miles)
  • Elevation Profile – Difficult (1600 metres elevation gain)
Okay, now things get tough... this route is not for the under-prepared—it takes you onto the hard hills of the Island, but also the best road cycling the Isle of Wight has to offer.

The route starts on Ryde Esplanade—easy to get to by Wightlink Fast Cat from Portsmouth (bikes go free) and with onwards connections to London and the South West by train. From Ryde, you head east to the harbour villages of St Helens and Bembridge—a gentle start to warm up the legs.

The route then continues to follow the Round The Island Cycle Route and passes through the villages of Adgestone and Alverstone, before reaching the seaside town of Shanklin. Here the climbing begins...

The road out of Shanklin—Cowlease Hill—is a substantial climb. It takes you up, up, and over into the town of Ventnor. Here I recommend a cafe stop at the superb Ventnor Botanic Gardens Cafe (the hottest garden in the UK). You will need some fuel for what is to come next...

Seven Sister's Road up through St Lawrence is a lung busting climb, which will leave you scrambling for gears. Once at the top, you are offered a brief respite as you roll down to Whitwell, but then Blackgang Road begins...

Up and over Blackgang, then inland to Carisbrooke via the hills of Chillerton. You then turn south again, out through Bowcombe; up and over Shorwell Shute and through to Brighstone. The hills do not stop.

Brighstone's Strawberry Lane is another leg beater; but at least from the top you can descend down to Calbourne and a pit-stop at the West Wight Alpaca Farm (around 80 kilometres)—great coffee, cake, and pizza.

The route then heads through to Freshwater Bay and onto the Military Road; more climbs, but more incredible views. You head back down for a second attempt at Blackgang—this time from the western side (it is steeper from this side)—before looping down to St Lawrence for yet another climb up Seven Sisters Road.

Hopefully, your legs have enough power to get you out of Ventnor again, and heading north back towards Ryde. If you feel like you need to reward and refuel yourself (which you most definitely deserve) then head to The Garlic Farm at Newchurch (125 kilometre mark) for some superb late lunch or dinner, before continuing back to Ryde.

Tim Wiggins Best Road Cycling Routes on the Isle of Wight

Wight Road Route #4 – A Military Mission

  • Difficulty – Hard
  • Distance – 135 kilometres (82 miles)
  • Elevation Profile – Difficult (1600 metres elevation gain)
The Military Road is a real highlight of the Isle of Wight, and riding the full length of it from Chale to Freshwater Bay is something of a 'bucket list' item for visiting road cyclists.

This route starts at Ryde again, heading south to the hills of Ventnor and onwards over Blackgang Road for the first of two ascents on the route.

You ride inland towards Carisbrooke and then back out west through Brighstone Forest and over Brook Shute.

From Brook, you descend down to harbour town of Yarmouth. At the harbour side there is my favourite bakery – Grace's Bakery; grab a doughnut and a takeaway Island Roasted Coffee and enjoy it sat on the quay.

Refuelled and caffeinated, you ride out to a highlight of the Isle of Wight – The Needles. The road up to the coastguard cottages is only open to pedestrians and cyclists, and makes for a superb switch-back climb to one of the best viewpoints on the Isle of Wight.

From The Needles, it is a fast and fun descent down to Freshwater Bay, then a climb out onto the famous Military Road. With a prevailing south westerly wind, you often enjoy a beautiful wind assisted spin along this pristine strip of tarmac; taking in the views out over the English Channel.

At the end of the Military Road it is time for another ascent of Blackgang—this time from the west side. Push hard, and then enjoy the descent down to Niton and onwards towards the centre of the island.

Stop off for lunch at Caffe Isola as you pass through Newport, then your legs will be prepared for the final few kilometres back to Ryde.

Tim Wiggins Best Road Cycling Routes on the Isle of Wight

Wight Road Route #5 – IOW Randonnee TX

  • Difficulty – Hard
  • Distance – 130 kilometres (80 miles)
  • Elevation Profile – Difficult (1700 metres elevation gain)
The Isle of Wight Randonnee is well known for being one of the best attended and best organised free cycling events in the UK. The permanently signposted route is easy for anyone to follow, and the standard loop is 100 kilometres long with around 1200 metres of elevation.

This revised route is one of my 'TX' series of routes (more of those in a future blog post). It is the more Xtreme version that I have personally tailored to take in some of my favourite climbs and stopovers.

I will let you find out for yourself where these additional vertical height gain treats feature; but for reference the refreshment stops are Grace's Bakery on Yarmouth quayside, The Garlic Farm at Newchurch, and Baywatch on the Beach at St. Helen's.

Ride out... and enjoy.

Tim Wiggins Best Road Cycling Routes on the Isle of Wight

Enjoy the fantastic road cycling on the Isle of Wight.

Isle of Wight Routes and Local Cycling Knowledge

Drop me a message on Twitter (@timwiggins1) or Instagram (@tim_wiggins1) with any questions.


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