9 of the maddest and raddest sportives of 2019

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Looking for an event to focus your cycling next year? Then here’s a round-up of bucket-list sportives for every style of riding

Sportives are as varied as they are fun, with more and more events popping up in the UK and further afield every year. To help you choose the ones you most want to ride, we've put together a (very unscientific) list of the most interesting sportives out there.

Most beautiful

What: Tour of Pembrokeshire
When: 18 May 2019

It’s hard to pick just one beautiful ride when there are so many sportives in some of the UK’s most gorgeous areas. But how about the Tour of Pembrokeshire which, on a sunny day like the 2017 edition, is pretty damn photogenic?

Most breathtaking


What: Cape Town Cycle Tour
When: 10 March 2019

If you feel like roaming further afield than south-west Wales, how about South Africa? The Cape Town Cycle Tour is a truly spectacular mass start ride, with more than 30,000 participants. Think RideLondon, but with more white sand beaches and fewer Surrey A-roads.

Most hardcore

What: Trafalgar Way – 300 Series
When: TBC

Woooweee… when it comes to super-tough sportives, you really can take your pic these days. How about the Trafalgar Way, though? Created to help fundraise for Cancer Research, this 500km (if you do the full ride) epic of epics follows a route that connects Falmouth in Cornwall with London, and traces the same roads taken by news of the Battle of Trafalgar in the 19th Century – hence the name. You can enter as teams, or solo, and there’s a bunch of different variants that combine sections of the full route if you don’t have 500km in you.

Most friendly

What: Tour de Yorkshire Sportive
When: 5 May 2019

Few places in the UK are friendlier than Yorkshire, with even fewer getting so enthusiastically behind cycling in the past couple of years. The Tour de Yorkshire features a women’s and men’s elite professional race, but for the rest of us mere mortals there's a sportive that takes place on the same day as the last stage of the men’s race. Covering between 50 and 100km, the routes comprise sections of the pro race, as well as some of the north’s most beautiful roads and challenging climbs. The one thing common to all the routes, though, is the warm welcome you’ll receive from roadside supporters throughout.

Most weird

What: Pittsburgh Dirty Dozen
When: TBC

The Pittsburgh Dirty Dozen is a ride around the US city that takes in 13 of its most difficult climbs. Eschewing the traditional beautiful landscapes most sportive organisers gravitate to, this ride is all about ‘enjoying’ the toughest ramps the industrial urban landscape has to offer. The climbs include brutal gradients of between 20 and 37%, which you can get a feel for in the video below. The event has been organised by local rider, Danny Chew, for the past 35 years.

Most iconic

What: Deloitte’s Ride Across Britain (RAB)
When: 7-15 September 2019

With the chance to see and feel more undulating inches of our fair Isle than ever before, Land’s End to John O’Groats (or LEJOG, as it’s affectionately nicknamed), is one of those rides that most seasoned cyclists have on their biking bucket list. 

Organised by Deloitte, a couple of the Casquette team took on this epic nine-day sportive last year. Although gruelling, they hailed it as a once in a lifetime – with awesome food and brilliant organisation. 

Most bone-shaking


What: Ronde Van Vlanderen Sportive
When: 6 April 2019

The Tour of Flanders in Belgium is a classic race that's famed for its rich history and boneshaking cobbles. With the introduction of a sportive the day before, now regular riders can follow in the tyre tracks of past winners like Elizabeth Deignan, Marianne Vos and Annemiek Van Vleuten.

If you're game, like Casquette contributor Laura Scott, you'll get to tackle iconic cobbled climbs such as the mighty Muur van Geraardsbergen, Koppenberg and Oude Kwaremont, before returning to the roadside the next day to watch the pro women and men’s races pass by. 

Most cultured

What: The Tweed Run
When: TBC

The Tweed Run sees immaculately-dressed cyclists take to the streets for a celebration of all things sartorial and cycling. Less sporting event, more an experiential exercise in pedalling with panache, the Tweed Run began in London, but has since expanded with one-off events around the globe. Typically, the Tweed Run involves a stop for tea, a picnic and awards for best moustache, vintage bicycle and headgear. Fancy pulling on your best Harris tweed and going for a spin? The next London Tweed Run is in May.

Most boozy (and foodie)

What: Eroica (various)
When: South Africa 16 March / California 7 April / Italy 28 April / Italy 26 May / Japan 1-2 June / Hispania 2 June / Britannia TBC / Netherlands 29 June / Germay 24 August / Dolomites 7 September / Gaiole in Chianti 6 October 2018

Booze and bikes obviously only go hand-in-hand if done with measure, but the Eroica festival adds cultural flair to proceedings. Hispania has local Rioja, while the Californian edition wends its way through Wine Country around Paso Robles, Eroica Britannia is all about a glass of refreshing ale, while the original event in Gaiole is all about rich red Chianti. 



Main image: RB Create

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