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Why autumn and winter is the perfect time to go riding on the Isle of Wight

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3 Nov 2021
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Rightly known as a cycling island, this is the perfect place to challenge and enjoy yourself in the later part of the year

The 2021 Tour of Britain is generally regarded as the most successful yet, with huge crowds watching the world’s finest cyclists beneath wall-to-wall sunshine. Well, the 2022 edition is set to be even bigger and better, with the final stage taking place in one of the UK’s famously picturesque spots – the Isle of Wight.

The honour of hosting the UK’s most prestigious race highlights the cycling appeal of the Island that sits just off the south coast of England. And that’s not just for the professionals. With hundreds of miles of cycle routes weaving their way through some of the most scenic countryside you could imagine, it’s easy to see why an increasing number of amateur cyclists are flocking to the Isle – whether you’re a roadie or gravel rider.

Of course, you need to get there first. And that’s easily done thanks to the myriad ferry routes from the mainland. If you’re heading over from the west, you might favour the Lymington-Yarmouth ferry.

Those based more centrally or out east might prefer either the Southampton-East Cowes or Portsmouth-Fishbourne/Ryde routes. Either way, the short trip across the Solent means it’s an option to head over early, ride the Island and return all in one day. But with so many routes and things to discover, it’s well worth staying for longer.


Credit: LeBlanq Isle of Wight

Round-the-Island ride

The most popular option for road cyclists is a 65-mile circumnavigation of the Island, exploring the whole of it in one day. Thanks to clear signposting, it’s easily navigated either clockwise or anti-clockwise. The choice is yours but just remember that, whichever way you ride, you’ll climb about 1,500m. Thankfully, you will do so on some of the smoothest roads you’ll find anywhere.

The roads are also famously quiet, ensuring you and your cycling compatriots can safely ride at pace. Or, if you prefer a more leisurely effort, perhaps taking a couple of days to cycle the Island, you can stop off at some of its many historic attractions.

Take Osborne House, which comes soon after leaving East Cowes and heading south-east. This is the former residence of Queen Victoria and where she died in 1901. 'It's impossible to imagine a prettier spot,' Queen Victoria said of her palatial holiday home.

It's worth a visit, as ornate furnishings and artefacts decorate the rooms and corridors where Victoria entertained heads of state. There's also the stunning Durbar Room, designed by Rudyard Kipling's father John Lockwood in an elaborate Indian style.

The east side of the Island is characterised by a series of short, sharp climbs that will really challenge your legs. Fortunately, you have bucolic and maritime backdrops to distract you, including Bembridge where yachts bob away beneath the Earl of Yarborough Monument, an immense obelisk of granite to commemorate the man who was the first Commodore of the Royal Yacht Squadron at Cowes.

Continue onwards and you'll pass Appuldurcombe House, the imposing 18th century Baroque country house whose rich, outrageous history spawned the film The Scandalous Lady W starring Natalie Dormer. Then it's onto the fringes of Ventnor, the seaside town that became the most popular health resort of Victorian times thanks to its unique microclimate.

It's well worth a meander off the main cycle route to stop at one of the many pubs and cafes that overlook the English Channel. You can't go wrong with freshly caught fish and chips from the Ventnor Haven Fishery or a swift pitstop at The Spyglass Inn.

After that, ride on up the west side of the Island, past Blackgang Chine, which is the oldest theme park in the UK having opened in the 1840s. This is definitely a must-do if your cycling coincides with a family holiday with the kids. You and your children or grandchildren won’t forget the memorable eccentricity of Rumpus Mansion, the Valley of the Dodos and Cowboy Town.


Credit: LeBlanq Isle of Wight

Riding variety

Circumnavigating the Island is a ride of two halves. While the east is pitchy and dominated by trees, the west is open fields and relaxing views of the Channel. Its climbs are higher and more challenging, with more gradual ascents, ensuring the route provides the variety sought for a long day in the saddle.

Some of the west side is flat, especially parts of the Military Road, which takes you at speed through an Area of Outstanding Beauty and along the Tennyson Heritage Coast, named after Poet Laureate Alfred Tennyson, who sought escape here from his legion of fans in the 1850s. Tennyson was at the centre of what became known as the Freshwater Circle, a creative collective that included Lewis Carroll, Edward Lear and William Allingham as well as Victorian photographic pioneer Julia Margaret Cameron.

The Isle of the Wight is a literary Island. And a dinosaur Island. Take Compton Beach, which you pass before the ascent and subsequent rapid descent to Freshwater, which is known as fossil nirvana, with its famous dinosaur footprint that’s still visible at low tide. A guided fossil walk is the perfect way to spend a relaxed autumn afternoon if you're in need of a break from the saddle.

As you head back to your starting point, the Solent will once again come into view. And often under sunshine, as the Isle of Wight is one of the sunniest places in England, enjoying an average 37 hours of weekly sun compared to 29 on the mainland. That and the rich soil is why everything, from garlic to grapes and hops, grows so well. You can enjoy all three with a visit to the Garlic Farm, Adgestone Vineyard, and some home-brewed beer at Ventnor's Botanical Gardens. Or you can finish your ride at Cowes and enjoy the fantastic wealth of fresh produce used by the finest chefs at eateries like Mojac's and Number 3.


Credit: Wight Prestige - James Cripps

Growing gravel popularity

It’s not all about the road, of course – the Isle of Wight has become a haven for gravel riding with an array of routes for all abilities. Take a 43-mile ride from Ryde on the east of the Island where your initial bridleway blast passes Quarr Abbey, constructed of Flemish brick and one of the most important 20th century religious buildings in the UK. The monks who lived and worked here were, like Belgium's more famous Trappists, known for brewing their own beer. Nowadays, it’s more about growing produce to supply the on-site teashop.

After a swift loop around Wootton Creek, you head inland to the hills. Be prepared here as once you've descended to Havenstreet, you head off-road up onto Arreton Downs along a wide chalk path. It's a challenge but worth the effort, not only for the views, but also the exhilarating descent that follows.

Continue forth over a mix of off-road, cycle paths and country lanes before a sandy track returns you to Arreton Valley where you rejoin the cycle track and head east. This is the perfect time to refresh and refuel at Pedaller's Café, situated on the cycle path at Langbridge.

After around 700m of climbing, taking in the beautiful surroundings of Brading Down and St Helens, it's a short climb to Nettlestone and then a relaxed effort along the seafront back to your starting point at Ryde.

It's just one of many gravel rides all over the Island, offering breathtaking views and variety depending on your fitness level. And like the road routes, any kind of bike is welcome, from entry-level gravel bikes to top-end e-bikes.

Ultimately, whatever you're riding, and whether you're staying for a day or a month, the Isle of Wight offers road and gravel riding that's unparalleled anywhere in the UK. And because of its southerly location, you'll enjoy longer daylight hours for riding into autumn and winter. It's time to brighten up the next few months with a cycling holiday in the Isle of Wight.

Learn more about what the Isle of Wight has to offer