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Britain's best cycling destination? The Isle of Wight delivers quiet roads, punchy climbs and endless sea views

26 Feb 2021

Want to feel like you’re going abroad without leaving the UK? The Isle of Wight offers quiet roads, punchy climbs and endless sea views

Words: Jack Elton-Walters Photography: James Cripps

Sense of place is a strange thing. When you feel like you belong somewhere the emotional response can be powerful, and it’s a sensation that washes over me as I pedal out onto the pristine tarmac roads of the Isle of Wight.

I live in London these days, but for me the Isle of Wight will always be home. I was brought up here, and seeing the island’s cliffs and beaches again brings memories flooding back of days spent riding the lanes when I was younger.

I may now live on the mainland, but in my heart I remain a Caulkhead (as we Islanders are known) and my flag is shades of blue interspersed with white.

For me today’s ride is not so much about exploring somewhere new as reacquainting myself with my home after a period away. Although not everything is the same as when I left. I remember the roads here used to be in an atrocious condition, so it’s a welcome change to discover that many of them are now wonderfully smooth and inviting.

Still, the peak of a heatwave and in the midst of a global pandemic may not seem like the best time to embark on a 130km ride here, but those are the conditions in which we head away from Ryde Pier in the northwest of the Island.

Fortunately our ride has coincided with a period of relaxed restrictions during the summer of 2020, so we are fully Covid-compliant. It also helps that my ride partner for today is my sister, Arielle.


Family affair

It’s still early in the morning, and with a light sea breeze and the sun not yet too high, the opening kilometres are extremely pleasant as we catch up on each other’s news. The main theme of today’s ride is the duality of coastlines and country lanes, so I have been careful to include the punchiest of climbs and finest of views.

Our route will take us first in an easterly direction, before heading south and then west all the way around the edge of the Island to the westernmost tip, before tracing an irregular course across the centre, via some of the Isle of Wight’s most picturesque lanes, to bring us back to our start point in Ryde.

The main topic of conversation during the first 10km towards the Island’s eastern tip is where we should stop for lunch. Maybe it’s all the fishing boats we pass along Bembridge Embankment that puts us in mind of food.

By the time we’ve passed through the village of Bembridge – much in need of pedestrianisation – and out into the rolling hills beyond, the conversation has changed to the topic of moustaches.

Arielle reminds me just how much one of our cousins hates moustaches, which is a none-too-subtle jibe at my own attempts to grow just such a facial accoutrement. I explain that I have been trying to coax one out of my top lip since Boris Johnson’s three-word phrase of choice was ‘stay at home’. I’m saved from any further enquiries into my suspect reasoning by the sudden appearance of the town of Brading.

The main road that circumnavigates the Island passes through Brading and we could turn off here to follow it around the coast. However the road can be busy with traffic on any normal weekend, let alone during a rare period of travel freedom when tourist numbers seem to be back to levels not seen since the launch of foreign package holidays.

Instead we opt to make our way on quieter lanes through the villages of Adgestone and Alverstone, flanked by high hedges throughout.

The roads are narrow enough that cars tend to avoid this route so we’re untroubled by motor traffic, and the shade from the hedges is welcome as the temperature starts to rise into the high 20s.

These early kilometres through gentle countryside are very enjoyable, although I’m aware that this is merely a warm-up and that the main test of the day is not far away.

Having completed around 25km of our ride we turn onto a main road that takes us back out to the coast at Shanklin, and once we have sauntered through the seaside resort’s beautiful Old Village, we emerge at the foot of Cowleaze Hill.

The deep south

The hardest climb of the day may not be the Angliru, but Cowleaze is still a real test for the legs, offering around 1.5km of climbing with gradients close to 15% in places. The reward for tackling the hill is one of the best views on the Island.

A quick glance to the left after the steep, early slopes reveals the beaches and blue sea of Sandown Bay, and the vista stretches across to the white cliffs of Culver in the distance.

Not that we can spend too long enjoying such vistas as the climb has a sting in its tail. It doesn’t finish quite where it feels like it should, and another kilometre of false flat chips away at our energy before we can recharge on the descent.

From here we trace the coast through Ventnor and Niton (not to be confused with Knighton, where locals know to pronounce the K: kay-nigh-tun), shaded by trees and pushed along by a cooling breeze until we emerge onto the exposed roads near Blackgang and get a taste of the promised 30°C temperatures.

Down here – the Island’s deep south – is, or at least was, smuggler country. In fact, a relative once assured me we were descended from the shipwreckers and bootleggers that prowled these coastlines.


To avoid fast-moving traffic on the long, straight Military Road we turn inland at Southdown and wind our way through the farmland and pretty villages of Atherfield and Yafford to the southern edge of Brighstone.

Of all the places I’ve ridden this area of the Island is my absolute favourite. I prefer it even to such cycling hotspots as Mallorca, the Alps or the cobbles of France and Belgium.

When the wind blows and the rain falls you can picture yourself riding in a spring Classic – the narrow, twisting lanes lending themselves to threshold efforts – yet when the sun is out there are few places that compare for relaxed summer riding.


I leave my reverie as we exit the lanes near Brighstone and rejoin the Military Road, and now it’s time to get out of the saddle again. We’re faced with the sun’s full blast as we take on a two-part climb between Compton Bay and Freshwater Bay to the west.

The first part hugs the coastline, and the effort of the climb is rewarded with a twisting descent before the longer second part eventually gives way to views of the azure waters and grey sand of Freshwater Bay.

We continue towards Alum Bay at the westernmost tip of the Island, famous for its multi-coloured sands and views out over the spires of white rock known as the Needles. We could haul ourselves up the dead-end climb to the viewpoint at the cliff edge, but we have other priorities. Lunch is calling.

Return journey

Off The Rails is housed in Yarmouth’s old train station. A victim of Dr Beeching’s rail closures, the building is now a cycle-friendly cafe and the old railway line a cycle track that’s perfect for a leisurely gravel ride.

We plan to stick to the roads, however, and after an excellent refuelling lunch we start our return journey across the centre of the Island. This part of the route takes in one of my favourite roads, Broad Lane, which arcs elegantly through farm fields with no hedge to obscure the view.

It was near here in August 1970 that Jimi Hendrix treated a crowd of 600,000 to his last live UK performance before his untimely death.


A haze of cloud moves in to cover the sun as we climb back over the Island’s central ridge towards Brighstone. A maze of country lanes takes us to the Newport-Sandown cycletrack, which we join at Horringford and enjoy a few clicks of traffic-free riding to Pedallers Cafe. It’s not on our agenda today, but is well worth a visit if you’re planning a ride here.

The last 15km to Ryde Pier includes a late couple of punches – the Lime Kiln Shute climb followed later by the climb to the crossroads at Upton. From here it is just about possible to roll without pedalling the final 3.5km to the seafront. Time it well and you can ride up the pier and onto the Wightlink Fast Cat.

Better still, why not stay and head out for another ride the next day? The Isle of Wight has plenty to offer.

Follow our route around the best bits of the Isle of Wight


To download this route go to

From Ryde Pier, head southeast through Nettlestone to St Helens and Bembridge. At Brading head inland to Whiteley Bank before turning back towards the coast at Shanklin.

Tackle Cowleaze Hill and descend to Ventnor, before tracing the coast all the way (bar a slight detour via Yafford) to Yarmouth in the northwest.

After lunch at Off The Rails, head southeast on Broad Lane before wiggling through Newbridge, Brighstone and Shorwell, then join the Newport-Sandown cycletrack at Horringford to Pedallers Cafe.

Turn north over the climb of Lime Kiln Shute, which rises over the Island’s main downland ridge before dropping back down towards Ryde.

Island life


Other stuff to do on the Isle of Wight

You’re 51 years too late to see Jimi

It was late August 1970 when Jimi Hendrix gave his last ever UK performance at the Isle of Wight Festival. Less than three weeks later he was dead after overdosing on sleeping pills.

In 2020 the festival itself fell prey to the pandemic, but it will return – fingers crossed – in June 2021. You just have to decide between Lionel Richie and Lewis Capaldi (

Drink and be driven

Music not your thing? How about a pub crawl on a bus? The annual Isle of Wight Beer And Buses Weekend ( takes place in October and involves an army of vintage buses that ferry people – for free – between pubs and clubs to enjoy the island’s boozy hospitality. It’s a very pleasant way to spend your recovery day.

That’s all in the past now

History buffs can visit 900-year-old Carisbrooke Castle, where King Charles I was imprisoned before his execution in 1649. Or for a bit more opulence try Osborne House, an Italian-inspired mansion near East Cowes that was Queen Victoria’s favourite getaway.

The rider’s ride


Canyon Ultimate CF SL Disc 8.0 Di2 Aero, £4,449,

I really couldn’t have asked for a more suitable bike for this ride than the Canyon Ultimate CF SL Disc 8.0 Di2 Aero – and the reason is explained in that ridiculously long name.

The Ultimate is Canyon’s go-to race bike, meaning it is every bit as stiff and responsive as you might hope for, which is handy on the short, steep climbs around this route. The ‘CF SL’ bit refers to ‘carbon fibre super light’, which the bike certainly is, and the ‘Disc 8.0 Di2’ bit relates to the spec, which is impeccable for the price (midway between the top-spec 9.0 and lower-spec 7.0), including a Shimano Ultegra Di2 Disc groupset and light, fast DT Swiss ARC 1400 Dicut wheels.

Finally, the ‘Aero’ part refers to those 50mm deep wheels, plus the neat aero cockpit and wind-tunnel-optimised tube shapes – just what you need on the flat, exposed parts of this island ride, of which there are many.

Canyon’s own VCLS seatpost is designed to flex, and therefore makes the Ultimate a comfy perch. It seems that Canyon has thought of everything, and it comes at a price that few other brands would be able to match.

How we did it

Travel and accommodation

Cyclist caught the Wightlink Car Ferry ( from Portsmouth to Fishbourne, about 5km from the start point of our ride on Ryde Pier. Ferry prices start from around £15 for a foot passenger with a bicycle and go up to over £100 for a return trip with car during peak season.

There is also a Wightlink Fast Cat that doesn’t take cars but docks right at the end of Ryde Pier, so makes an excellent option for a day trip. The Fast Cat crossing takes just over 20 minutes compared to 45 minutes for the Fishbourne ferry. Other ferry options include Southampton to Cowes or East Cowes and Lymington to Yarmouth.

Once on the island there is a wealth of hotels, B&Bs and campsites to choose from, with prices to suit every budget. See for information.


Many thanks to Adrian’s Bike Shop in Freshwater for all the help with mechanical support and couriering of bikes on and off the island –,

Thanks also to Performance Comms and Skoda UK ( for the loan of a car, allowing for a coronavirus-free journey to and from the Isle of Wight with plenty of space in the Skoda Karoq for bikes and kit.

The addition of the Karoq-specific bike rack was a welcome bonus.


Pick of the kit



Bike: Canyon Ultimate CF SL Disc 8.0 Di2 Aero, £4,449,  
Helmet: Specialized S-Works Evade II Mips helmet, £240,  
Jersey: Pearl Izumi Pro Air jersey, £199.99,  
Gilet: Pearl Izumi Zephrr Barrier gilet, £89.99,  
Arm warmers: Pearl Izumi Elite Thermal Arm Warmer, £14.99  
Gloves: Pearl Izumi Pro Gel gloves, £44.99,  
Shorts: Pearl Izumi Pro Air bibshorts, £249.99,  
Knee warmers: Pearl Izumi Elite Knee Warmer, £39.99,  
Socks: Pearl Izumi Attack Tall socks, £12.49,  
Shoes: Specialized S-Works 7 shoes, £360,


Bike: BMC Timemachine Road 01 Ultegra Di2, £5,747.99,;
Timemachine 01 Road Force eTap AXS available from  
Helmet: Abus Aventor, £72.49,  
Sunglasses: Rudy Project Tralyx Slim, £125.99,  
Jersey: Rapha Women’s Brevet Jersey II, £130,  
Gilet: Rapha Insulated Brevet Gilet, £130,  
Gloves: Specialized Body Geometry Sport Women’s, £25,  
Shorts: Rapha Women’s Cargo Bibshorts, £195,  
Socks: GripGrab Merino Lightweight Sock SL, £16.16,  
Shoes: Fizik R4 Tempo Overcurve, £175.49,