Ultimate cycling challenges 2021: 12 of the world’s best cycling events Back to top
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Ultimate cycling challenges 2021:
12 of the world’s best cycling events for your road cycling bucket list

For those of you who have completed a local UK sportive and perhaps one in mainland Europe, you may now be looking at many of the ultimate cycling challenges that will be staged around the world in 2021.

Many cycling events and challenges were cancelled or postponed in 2020, due to the Covid pandemic, but organisers around the world will be hoping that 2021 is different. 

There are some events that you can complete at a time of your choosing, such as a ‘Ride across America’ or ‘Everesting cycling’ (multiple ascents of a particular climb in which the cumulative elevation equates to the height of Mount Everest), but the majority happen at a set time on a set date, are extremely popular and a real test of mind and body. 

Here are 12 of the best cycling challenge ideas which you may wish to consider adding to your cycling bucket list for the year ahead. (Just make sure you check your travel insurance and the event's cancellation terms before you book!)


Written by John Vicars

Note: due to Covid-19 and other unforeseen circumstances, all of the dates and details listed here are subject to change. Check with the organisers before booking.

If you'd like a nice reminder of your sportive, these beautiful GPX-based prints are a great idea. More details at the bottom of this article!

Custom map makes a unique cycling gift

Example Bilbao to Barcelona ride

GPX based custom map print

Example LEJOG ride


North America Cycle challenges

1. Gran Fondo New York City (GFNY)

Location:  

New York City

date:  

16 May 2021

Distance:

80 or 160 kilometres (50 or 100 miles)

Our view:

Part of the world wide GFNY series of events, this ever popular sportive is seen by some as one of the best gran fondos in the USA.


The GFNY NYC serves as the World Championship for the GFNY World Series of races.


It as billed as a personal endurance event: a competition against the clock and fellow riders. The route starts at the historic George Washington Bridge on the Hudson River, just north of Central Park, and embarks upon a 100 mile (161 kilometre) circular route of New York City. 


At the halfway point you crest Bear Mountain which is the highest point within the city limits. You can either finish your ride here or continue along the rolling terrain (total elevation 2,800 metres) back to the starting point near Fort Lee. The event comprises of a mass start and is chip timed with closed roads or police moderated traffic junctions.



Conclusion:

The one to do for riding closed roads in one of the most famous and iconic cities in the world.

2. Trans Am Bike race

Location:  

Oregon, USA

date:  

Awaiting information

Distance:

6,800 kilometres (4,200 miles)

Our view:

Note: as at 21 December 2020, the organisers have not yet announced details for the 2021 event, so the information here is based on previous events.


The objective of this endurance epic is quite simple; cycling across the USA, racing from Oregon in the west to Virginia in the east, along the Trans am trail as quickly as possible in a solo and self-supported manner.


This epic journey is 4,200 miles (6,800 km) long and passes through no less than ten states taking you from the Pacific to the Atlantic Oceans. The fastest riders complete the course in around two and a half weeks whilst many others opt for a more sedate pace and see the event more as a 30 day cycling challenge.


A very unique bicycle challenge but if you have the time and physical ability what a great way to explore the country by cycling coast to coast in the USA and completely at your own pace as there are no cut off times.


Conclusion:

If ultra endurance riding is your thing, this is one of the ultimate events out there!


If you fancy doing it yourself, outside of the official race, you'll enjoy this article: Biking across America: tips and insights on how to ride across the USA.

3. Tour of Utah Ultimate Challenge

Location:  

Park City,  Utah,  USA

date:  

Awaiting information

Distance:

150 kilometres

Our view:

Note: as at 21 December 2020, the organisers have not yet announced details for the 2021 event, so the information here is based on previous events.


Running just a few days ahead of the Larry Miller Tour of Utah (the biggest UCI sanctioned stage race in North America), amateur cyclists are given the opportunity to compete in the Ultimate Challenge held over 150 kilometres with 2,500 metres of elevation.


Advertised as America’s toughest one day cycling adventure, the course mirrors the Queen stage of the pro race incorporating all the climbs and has two timed segments on Wolf Creek Ranch Road and on the Pine Canyon Road to Empire Pass.


It is a great opportunity to test yourself on an epic stage of one of the toughest professional races in the country. It’s a real USA pro cycling challenge.


Conclusion:

A fantastic event with the opportunity to ride the same roads as the pros.

4. RBC Gran Fondo Whistler

Location:  

Vancouver, Canada

date:  

11 September 2021

Distance:

55, 122, 152 kilometres

Our view:

In 2020 the RBC Gran Fondo Whistler was due to host the official UCI Gran Fondo World Championships, featuring those cyclists who have qualified from the 27 world-wide preliminary events. Of course that event was cancelled - but you can still ride this incredible course as a normal sportive.


The Whistler Gran Fondo typically sees 5,000 participants, making it the largest Gran Fondo in North America. 


The gran fondo crosses the iconic Lions Gate bridge before travelling along the world-famous Sea-to-Sky highway descending towards the Pacific ocean before rising again up to Whistler in what can only be described as one of the best cycling events in the world.


Conclusion:

A rare chance to ride an award-winning Gran Fondo in an incredible setting.

Lions Gate Bridge Whistler gran fondo

Opportunity to cycle the iconic Lions Gate Bridge in Vancouver

European cycling challenges (inc UK)

5. Trans Pyrenees race

Location:  

Llançà, Spain

date:  

26 June 2021

Distance:

1,100 kilometres

Our view:

The Trans Pyrenees is one of the most well-known cycling challenges in Europe: a self-supported, ultra-distance cycling event which takes the form of a 1,100 kilometre route (25,000m of climbing) from the Mediterranean to the Atlantic coast. It includes some of the most mythical and challenging cols in the Pyrenees such as the Pailhères, Peyresourde, Tourmalet, Luz-Ardiden, Aubisque and Marie Blanque.  


Starting in the far north eastern corner of Spain near its border with France in the town of Llançà, the route takes a westerly route through some spectacular remote scenery in the Pyrenees and finishes in the Basque city of San Sebastian.


This is not a traditional sportive as it takes the form of a self-supported, bike packing challenge where all competitors have to follow the official route and find their own food and drinks.


Note: this is a different event to the new 1,500km self-supported Trans Pyrenees event run by the same team as the Transcontinental Race. That route goes from the Bay of Biscay to the Balearic Sea and back again. The inaugural event was due to take place in 2020 but was prevented by Covid. 


Conclusion:

This is a classic bike ride challenge that will attract the fittest of ultra endurance riders and those who are able to climb – certainly not a cycling challenge for beginners.


If you're interested in riding across the Pyrenees outside of the Trans Pyrenees race, read our article on the Raid Pyrenees.


6. Tour du Mont Blanc

Location:  

Les Saisies, France

date:  

17 July 2021

Distance:

338 kilometres

Our view:

Referred to as "the world's toughest one day bike race", there is only one word to describe one of the most popular cycling events in France – brutal. 


Starting at 5am in the French ski resort of Les Saisies, you have the daunting challenge of 338 kilometres (210 miles) with 8,500 metres of elevation to complete in just one day!


The route, which circles Mont Blanc, runs clockwise through the Chamonix valley and the Col de Forclaz before a long descent into Switzerland. There’s then a long climb up the Col du Grand St Bernard which takes you over the Italian border into Aosta. Having climbed the Col du Petit St Bernard you are back in France heading for Bourg St. Maurice and after another col, the Cormet de Roselend, there is a final ascent back to the starting point.


Conclusion:

If you are looking for a double century cycle challenge that's going to push you to the limits (and beyond!) then this is the one! 

7. Transcontinental race

Location:  

Brest, France

date:  

July/August 2021 (Awaiting confirmation)

Distance:

4,000 kilometres

Our view:

Note: as at 21 December 2020, the organisers have not yet definitively confirmed their plans for the 2021 event, so the information here is based on previous events.


The Transcontinental Race describes itself as "the definitive self-supported bicycle race across Europe".


It is an epic endurance race which spans the breadth of the European continent taking place on open roads across several countries. In 2019 the event was won by a female rider from Germany who completed the 4,000-kilometre course from Burgas in Bulgaria to Brest in France in 10 days and 2 hours. 


The parcours is altered each year and the 2020 edition sees the route from the previous year reversed with the organisers including sections of unpaved and gravel surfaces. Competitors will also be faced with the ascent of the Carpathian Mountains. 


Similar to other endurance races, this is a totally self-supported challenge with the rider choosing how long to stop to rest and being responsible for sourcing their own food and drink. 


Conclusion:

The Transcontinental is often viewed as the ultimate endurance challenge.


You can read our Q&A with former Transcontinental winner, Emily Chappell, here.


8. Land's End to John O'Groats

(on the Deloitte Ride Across Britain event)

Location:  

Land's End, Cornwall

date:  

4-12 September 2021

Distance:

980 miles

Our view:

LEJOG is often referred to as the ‘Daddy’ of all cycling challenges in UK. It starts at Land’s End in south west Cornwall and ends at John O’Groats in northern Scotland. There are many different routes, with the shortest being around 900 miles, but if you decide to avoid major roads and add on the additional mileage to your accommodation each evening most participants complete around 1,000 miles on the challenge.


Often people who enter LEJOG are aligned to a charity as part of a charity cycling challenge. It’s been completed on lots of different sorts of bikes from conventional road bikes, to fixed gear bikes, tandems and even a penny farthing! Some even walk the route. 


Of course, you can ride Land’s End to John O’Groats (LEJOG) in the UK at any time of year, but the Deloitte Ride Across Britain makes an event out of the LEJOG route.  


The Ride Across Britain is billed as the challenge of a lifetime and this 9 day marathon covers 980 miles through some of the best and beautiful landscape you will find. The event is extremely well organised and fully supported. All you really need is your bike as food, drinks, mechanical and medical support plus a tent for each night is provided. The event has also started to develop as a corporate charity challenge.


Conclusion:

LEJOG is probably the biggest UK endurance challenge, a truly epic challenge that's sometimes beset by adverse weather and is guaranteed to push every participant to their physical and mental limits.

Lands End John O'groats for cyclists

Milepost sign at John O Groats in Scotland

9. Coast to Coast challenge

Location:  

Whitehaven, Cumbria

date:  

24 and 25 September 2021

Distance:

225 kilometres

Our view:

Much more achievable than riding south to north on LEJOG, the Coast to Coast Cycle Challenge takes two days to traverse England from the west coast in Whitehaven, Cumbria to Whitley Bay, Northumberland on the east coast. 


The route of 225 kilometres from the Atlantic Ocean to the North Sea takes you across some of the best scenery the country has to offer as well as giving you the opportunity to track along the ancient fringes of Hadrian’s Wall.


Day one takes in the super steep ascents of both Hardknott and Wrynose passes in the Lake District as you cover the first 105 kilometres to the overnight stop in Alston. The following day tracks through the Northumberland National Park as you head towards and then bypass Newcastle upon Tyne before finishing at the lighthouse at Whitley Bay.


As with LEJOG there are other (west to east) routes that you can take to fulfil one of the most popular UK cycling challenges around. Also many people do it with different charities/travel operators or DIY outside of an official event. If you are really up for a challenge then why not do it all in one day!


Conclusion:

The Coast to Coast is a more manageable UK endurance challenge than LEJOG, while still being a fantastic event to be part of.

Other European cycling challenges

We’ve focused on the longer distance events here, but also check out our pick of the best sportives in the UK and the best cycling challenges in Europe (excluding the UK).

Rest of the world

10. Cape Town Cycle Tour

Location:  

Cape Town, South Africa

date:  

14 March 2021

Distance:

109 kilometres

Our view:

This Cape Town cycling event has now become one of the largest timed cycling sportives in the world. Formerly known as "The Argus", the event attracts more than 35,000 cyclists from all over the globe each year and concludes an eight-day ‘Lifecycle week’, which is provisionally due to run 7-15 March 2021 and is a city-wide celebration of all things cycling.


This extremely popular event takes in 109 kilometres (1,220 metres of elevation) of scenic beauty as it loops around the Cape. 


Starting in the city centre the route circles the Cape Peninsula; it starts and finishes close to Table Mountain, which is one of the seven natural wonders of the world.


After the start, the route makes its way southerly down the west coast to Smitswinkel before turning north and east towards Scarborough and the Atlantic coastline before encountering the two climbs of Chapmans Peak and Suikerbossie. The sportive finishes with a downhill run into the Green Point area.


This cycling event in the western Cape is renowned for first class planning. The route has no less than 16 refreshment stations and 2,500 volunteers at hand to ensure it passes off smoothly and efficiently. 


Conclusion:

A long-established, very well-organised event in an iconic location.

Cyclists on the Cape Town Cycle Tour take in the Cape

Stunning Cape Town, South Africa

11. Taiwan KOM Challenge

Location:  

Taiwan

date:  

Awaiting information

Distance:

105 kilometres

Our view:

Note: as at 21 December 2020, the organisers have not yet announced details for the 2021 event, so the information here is based on previous events.


Staged every October, the KOM challenge is quickly becoming one of the most talked about cycle challenges in the world. 


Starting at Qixingtan beach by the Pacific Ocean at zero metres altitude, the 105 kilometre route takes you along severe uphill gradients (the last 8 kilometres see inclines between 17% - 27%) and through the majestic Taroko gorge before topping out at the peak of Mount Wuling at 3,275 metres. 


The event is staged in the cycling ‘off season’ and attracts a number of professional riders. In 2017 the Italian Vincenzo Nibali broke the course record, adding afterwards that it had been the longest and hardest climb of his life. 


Conclusion:

If you want an iconic cycle challenge, something quirky and unique then this is the perfect one for you.

12. Amy's Gran Fondo

Location:  

Victoria, Australia

date:  

24 October 2021

Distance:

45 and 130 kilometres

Our view:

Amy’s Gran Fondo has very quickly established itself as one of the most popular mass participation bike rides in the Australia.


It attracts more than 10,000 riders from all over the world with a particular emphasis on rider safety and ensuring that the event caters for cyclists of all abilities.


The event starts and finishes in Lorne, Victoria and is a closed road granfondo held arguably on one of the most picturesque destinations on the planet – the Great Ocean Road.


As part of the UCI Gran Fondo Competition, the long route takes in 130 kilometres and 1,900 metres of vertical elevation.


Conclusion:

Amy's Gran Fondo is one of the premier Australian cycling events, with the highlight being the opportunity to ride the Great Ocean Road.

Want something to help you remember your event?

These cycling map prints are just the ticket. How it works:

  • You upload a GPX file or connect to Strava and find your ride (you can add multiple day rides to one map). 
  • You use the map builder to create the print as you want it (you can alter the size, colour and text). 
  • You submit all the details and are then sent a preview to check before it's printed and sent to you.
    More info here. Prices start at £35.
Custom map makes a unique cycling gift

Example Bilbao to Barcelona ride

GPX based custom map print

Example LEJOG ride

What's next?

Have you done any of these huge rides or are you planning to? Let us know in the comments below, we’d love to hear from you!

If you're looking for more cycling challenge to inspire you, don't miss our articles on European cycling challenges and UK sportives!

Want more information on what Gran Fondos are and what they involve? Check out our Gran Fondo guide, here.


Read on!

16 of the best UK sportives 2021
We share 16 of the best sportives in the UK, and sort them by region to make it easy to find one close to you.
11 best cycling challenges in Europe 2021: sportives, gran fondos and more!
Our guide to 11 of the best cycling challenges in Europe for 2021, including top sportives, gran fondos and cycling events
Ultimate cycling challenges 2021:
12 of the world’s best cycling events for your road cycling bucket list
Our pick of the world's ultimate cycling challenges - our favourite events that have life-changing potential!

About John Vicars

Cycling up Buttertubs Pass from Hawes

John divides his time between England and Spain and, together with his wife, clocks in around 10,000 miles each year searching out Europe's finest roads. John loves to share his experiences (good and bad) from the saddle and has a particular loathing for double digit gradients, sub-zero temperatures and red traffic lights!


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