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The best UK challenge rides you should take on in 2020

Cyclist magazine
11 Mar 2020

Eleven iconic UK cycling events and sportives – in no particular order – that every cyclist should try.

From the Scottish Highlands down to the New Forest, the UK manages far more varied scenery than it gets credit for. Within these gems are also some excellent riding challenges across the year that offer a proper test for even the toughest riders. 

So keep your travel plans simple and your carbon footprint to a minimum and choose an event close to home this year. Spanning sportives, events and just really tough bits of tarmac - here are the 11 best cycling challenges in the UK.

The 11 best UK challenge rides you should take on in 2020

London to Brighton

87km (54 miles)

One of the original cycle challenges, the first recorded London to Brighton bike ride was completed by John Mayall in February 1869 – riding a velocipede (an early bike which had the cranks on the front wheel). It took him around 12 hours.

Thanks to improvements in bicycles and road surfaces, it should take modern cyclists less than a third of that time.

It’s also the route for one of Britain’s biggest, longest-running charity rides – the British Heart Foundation’s annual 87km event, which features the iconic climb of Ditchling Beacon (1.4km, average 9%), has been run for over 40 years.

Next year’s edition is in June and expects a field of 25,000 riders.

Bryan Chapman Memorial 600

619km (385 miles)

Billed as ‘The Welsh End-to-End’, this popular, long-running ride takes you from the Severn Bridge in Chepstow, South Wales, up to Menai Bridge, Anglesey, via the glorious scenery of Snowdonia. And then all the way back again.

As this is an Audax ride, you’re expected to be self-sufficient. There is no mechanical support en route, and you will need to complete the 619km distance, with a total of 7,500m of ascent, within a time limit of 40 hours – which for most riders means riding through the night.

That said, both food and sleeping facilities are included in the £30 entry fee, Brucie Bonus. The next edition will be on 16th May 2020.

Find out

Bealach Na Ba

9.1km (5.7 miles)

Bealach na Bà is as close as Britain gets to an Alpine or Dolomiti climb. Located on the Applecross peninsula in the Scottish Highlands, this remote pass is worth the trip for the breathtaking views across the sea to the Western Isles alone.

Rising continuously for 626m over 9.1km, it climbs more than any other road in Britain, at a leg-sapping 7% average, maxing out at 20% on its steepest upper slopes.

If you want to make the climb part of a bigger adventure, it is included in two local sportives, the Bealach Beag (77km) and Bealach Mor (144km).

If you're heading out to complete it alone, make sure you go in the height of summer to avoid bad weather and limited daylight.

Find out more:

Dunwich Dynamo

193km (120 miles)

Riding through the night until dawn should be on every cyclist’s to do list. Country lanes take on a whole new character in the dark, with a soundtrack provided by owls and other nocturnal creatures. And watching the sun come up as night becomes day makes for a truly magical experience.

Scheduled to take place on the Saturday in July closest to the full moon, the Dunwich Dynamo is one of the most famous organised overnight rides.

Started in 1992 by a group of London bike messengers, the route takes you from North London through the Essex countryside to the lost village of Dunwich on the Suffolk coast (in the 14th century it was an international port similar in size to London that was largely gobbled up by the sea).

This special ride attracts over 2,000 participants; entry is free and a party atmosphere is guaranteed. Next year's event will be on Saturday 4th July.

Find out more:

Land's End to John O'Groats

1,406km (874 miles)

Another challenge almost as old as cycling itself. The first recorded attempt at the ‘End to End’ was in 1873, when four members of the Middlesex Cycling Club rode the 874 miles between mainland Britain’s two furthest points.

The enduring appeal of this epic adventure sees thousands of cyclists attempt it every year, from legendary endurance racer Andy Wilkinson, who holds the record for completing the distance in a little over 41 hours, to tourists taking a couple of weeks to enjoy the scenery.

The fully supported Deloitte Ride Across Britain sees 800 riders take on a 1545km version of the route via some of the nation’s most spectacular scenery over nine days. The 2020 edition will take place from Saturday 5th September.

Find out more:

Tour de Yorkshire Ride

102km (63 miles)

As part of the legacy of the 2014 Tour de France visit, the Tour de Yorkshire isn’t the oldest pro race in Britain but it is fast becoming one of the most prestigious, attracting some of the biggest names in the sport.

The associated sportive is your chance to experience some of the magic for yourself, taking place on the same roads and on the same day as a stage of the pro race, featuring the stunning scenery of Yorkshire and some challenging climbs.

The yearly sportive starts and finishes in Leeds, a big, bustling city with plenty of accommodation options to boot. Next year's ride will be on 3rd May.

Find out more:

Dragon Ride

305km (189 miles)

One for those who like their sportives really tough, the Dragon Ride added a whole new level of difficulty in 2014 when it introduced the 305km ‘Dragon Devil’ option, alongside the 153km and 230km routes.

Signature hills include Rhigos, 6km at 5%, with stunning views across the Black Mountains from the summit – and all the way to the sea on a clear day.

But perhaps the hardest is the Devil’s Elbow, a brutal 1.5km climb – rising 450m with an average gradient of 15%! It comes towards the end of the ride, so your legs will already be burning by the time you reach it. The 2020 date will be Sunday 7th June.

Find out more:

Tour of Wessex

530km (330 miles)

One of the world’s biggest multi-day sportives, the Tour of Wessex takes you through the lanes and byways of the southwest, with three stages packed with history, monuments and challenging climbs.

You can take on the full distance of 330 miles (530km) spread over three stages, or you can opt for the shorter version at 250 miles, or just take on a single stage.

If you attempt the whole thing, you’d better bring your climbing legs, because there’s 7,672 metres of ascent in total, including the fearsome climb of Cheddar Gorge, plus other attractions such as Lulworth Cove and the Cerne Abbas Giant chalk figure.

Find out more:

Fred Whitton Challenge

180km (112 miles)

The local club ride that became a legendary sportive, the Fred Whitton has been run annually on or near May bank holiday weekend by the Lakes Road Club since 1999 and now with the expertise of Human Race Events, raising money for cancer charities in memory of a former club secretary.

It’s not hard to see the appeal – the ride takes in just about every noteworthy climb and leg-busting pass in the Lake District – Kirkstone, Honister, Hardknott, Wrynose, Newlands, Whinlatter… Our legs wobble just thinking about it.

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The M25 Orbital Ride

257km (160 miles)

The beauty of the M25 Orbital ride is that it's just a massive 260km circle meaning you can literally start the ride anywhere! Uxbridge, Dartford, Enfield, it doesn't matter. You end where you start anyway.

A real test of endurance, this ride will take you on a huge loop of London's ring road, taking in its bordering counties and areas including the Surrey Hills and parts of the Chilterns. The route will have you weaving in and out of the M25 as you slowly but surely work your way home.

This isn't the most scenic of routes but it's immensely satisfying when you get to the finish.


1,433km (890 miles)

The idea of cycling between the English and Scottish capitals and back again already sounds daunting, but completing it inside five days?

That’s the challenge of London-Edinburgh-London, the flagship event of Audax UK, the long-distance cycling association.

Starting with a prologue on London’s Mall, outside Buckingham Palace, the route heads up the east of England through Cambridge, over the Humber Bridge before crossing the Pennines and meandering up through the Scottish Borders region.

Held every four years, the next edition will be in August 2021 – so not next year like the rest on the list, but that means there’s plenty of time to get training!

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