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 2023.

Many top cycling events and challenges were cancelled or postponed in the Covid years, but now with the vaccine rollout and restrictions loosening, organisers around the world will be hoping that 2023 will be business as usual.

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 13 of the best and sometimes extreme cycling challenge ideas 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!)

Looking for info on how to train for long distance cycling events like this? Read on.

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In the interests of complete transparency, we haven’t (yet!) cycled all of the routes/events in this article. If you have ridden any of these, let us know in the comments below!

North America Cycle challenges

1. Gran Fondo New York City (GFNY)

Location:   New York City
Date:   21 May 2023
Distance: 75 or 160 kilometres (45 or 100 miles)

Our view

Part of the worldwide 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 road cycling challenges.

It is 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 a mass start and is chip timed with closed roads or police moderated traffic junctions. The organisers tote it as a great way to experience being a pro for a day.


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




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2. Trans Am Bike race

Location:   Oregon, USA
Date:   4 June 2023
Distance: 6,800 kilometres (4,200 miles)

Our view

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. It’s similar to Race Across America, but without the inherent competitiveness of some other extreme cycling challenges

A very unique bicycle challenge for 2023, 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.


If ultra endurance riding is your thing, this is one of the ultimate long distance cycling events of 2023!

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 of December 2022, details are awaited on whether the Tour of Utah will return. It was scheduled for 2022 but later pulled, though there is hope it will return for 2023.

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 gain.

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.


A fantastic event with the opportunity to ride the same roads as the pros. This is your chance to test yourself on one of the tougher cycle challenges in the US.


4. RBC Gran Fondo Whistler

Location:   Vancouver, Canada
Date:   9 September 2023
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 in 2023 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. Normally a place associated with mountain biking, this event really puts a shine on the quality road cycling in the area.

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 road cycling events in 2023.


A rare chance to ride an award-winning Gran Fondo in an incredible setting. This is up there amongst the top road cycling events you could choose for 2023.


Lions Gate Bridge Whistler gran fondo Opportunity to cycle the iconic Lions Gate Bridge in Vancouver

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 giftExample Bilbao to Barcelona ride
GPX based custom map printExample LEJOG ride

European cycling challenges (inc UK)

5. Trans Pyrenees race

Location:   Llançà, Spain
Date:   24 June 2023
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.


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:   15 July 2023
Distance: 330 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 long distance cycling events in France – brutal.

Starting at 5am in the French ski resort of Les Saisies, you have the daunting challenge of 330 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.


If you are looking for a double century cycling challenge in 2023 that’s going to push you to the limits (and beyond!) then this is the one!



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7. Transcontinental race

Location:   Geraardsbergen, Belgium
Date:   23 July 2023
Distance: 4,100 kilometres

Our view

The Transcontinental Race describes itself as “the definitive self-supported bicycle race across Europe” and it’s one of the ultimate cycling challenges you can complete.

It is an epic endurance race which spans the breadth of the European continent taking place on open roads across several countries.

Unfortunately, in 2020 and 2021, the race was postponed due to the Covid pandemic. But it returned 2022 and was won by Christoph Strasser of Austria.

The parcours is altered each year and the 2023 edition sees the route beginning in Geraardsbergen, Belgium all the way to Burgas, Bulgaria.

There are multiple checkpoints that the riders must pass through for their ride to be counted. 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.


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:   7-15 September 2024
Distance: 980 miles

Our view

LEJOG is often referred to as the ‘Daddy’ of all cycling challenges in the UK, and is a rite of passage for many road cyclists. 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 (“RAB”) 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.

Since 2022, RAB has switched to become a bi-annual event. You can register now for 2024; the only event in 2023 will be virtual.


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.

If you’re interested in reading more about LEJOG, this in-depth article on LEJOG shares what to expect and a lot of useful information.


Lands End John O'groats for cyclists

Milepost sign at John O Groats in Scotland


9. Coast to Coast challenge

Location:   Whitehaven, Cumbria
Date:   Various
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 fulfill 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!


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


10. Haute Route Dolomites

Location:   Italian Dolomites
Date:   29 August 2023
Distance: 284 miles

Our view

The Haute Route series is famed for its routes around the steepest and most difficult climbs in Europe, and this one from the Dolomites is no different. The event takes place over three stages, and incorporates some of the most famous climbs in the mountain region, including the fearsome Passo Stelvio.

In 2023, the total elevation gain over the three stages is 14,850 metres, so you definitely need to bring your climbing legs!

The unique format for these events sees two more classic stages, as amateurs compete to finish as close to the front as possible over the two days. And finally, an uphill time trial stage, where you compete against the clock to finalise your rankings in the overall competition.

You can compete as either a solo entrant or as part of a team, depending on how you want to play things!


A cycling challenge for the climbers, this is three days of incredible views and mountainous scenery, but not enough to distract you from the pain in your legs!

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).

You might also like our pick of the best long distance cycling routes in the UK, Europe and worldwide.


Rest of the world

11. Cape Town Cycle Tour

Location:   Cape Town, South Africa
date:   12 March 2023
Distance: 42/109 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’, 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.

New for 2023, there’s a shorter out-and-back route at just 42 kilometres, if you don’t feel like traditional route is for you.


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


12. Taiwan KOM Challenge

Location:   Taiwan
Date:   Awaiting information
Distance: 105 kilometres

Our view:

Note: as at 29 December 2022, the organisers have not yet announced details for the 2023 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.


If you want iconic cycle challenges in 2023, something quirky and unique then this is the perfect one for you.

This article contains more information on the Taiwan KOM Challenge and this article has more general information on cycling in Taiwan.

13. Amy’s Gran Fondo

Location:   Victoria, Australia
Date:   10 September 2023
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 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.


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

(For anyone looking to ride in the region, check out our guide to the area, here. For those looking for something even more challenging, check out the Peaks Challenge Falls Peak!)

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 challenges in 2023 to inspire you, don’t miss our articles on European cycling challenges, UK sportives and cycling challenges for beginners!

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

Or if you’re looking for inspiration for the best cycling routes in the world, this is for you.

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.

Custom map makes a unique cycling giftExample Bilbao to Barcelona ride
GPX based custom map printExample LEJOG ride


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Clare Dewey

Clare Dewey is a road cyclist with a passion for travel. She set up to help make it easy for road cyclists to explore new places by bike.

Last Reviewed: 29 December 2022

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13 of the world’s best cycling events for your road cycling bucket list”

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