That is the general rule of progression that most triathletes will follow if they stick to the sport for a good few years. Those that have been in the sport for a long time often down-grade as they get a bit older and eventually end up with the sprint distances again as a final curtain call to their triathlon endeavours and careers.

What does it mean when we say the most challenging triathlon Events?

1. This would be a typical triathlon that goes beyond your current comfort zone. Some less challenging events can be taken on in a flash – a few weeks of training and you can get across that finish line. It does not have to be fast, but you can finish it comfortably. When it comes to the most challenging triathlon, not so much.
2. When race organisers tell you that sickness, injury, and danger might beset you during the challenge, you know you better be ready and up for it from the gun. Years of experience racing under different conditions and in different situations will give you the necessary muscle to take on one of these challenges.
3. You will need to be a little crazy. Not in the usual sense that we all know, but you will have to be one of those strong-minded individuals who are so focussed on your own ability that you are willing to take on a challenge that very few are prepared to do themselves.
4. You will need a lot of time on your hands and a good preparation plan in place. Some of these challenges might take a planning phase of between 1 and 2 years (depending on your current level of proficiency) before you even line-up at the start, so it's best to get yourself prepared for this part of the challenge.
5. You will need to have some extra money available. Events like these don’t come cheap and are often beset by additional costs that you will not find at the normal weekend get-away race.

Now that is out the way, here is a list of the some of the Most Challenging Triathlon events:

1. The Swiss ULTRA DECA Continuous

Try swimming 38km, then biking 1800km and finally ending off with a 422km run – all done within a time frame of 14.4 days. Would you be up for the challenge? We rate this as the toughest triathlon challenge on the planet. Besides requiring oodles of time at your disposal to complete the event spread out over 2 weeks, you will also need to be incredibly fit both physically and mentally.

With a few weeks left until the event takes place in August you should be far within workout schedule. We reckon there is no bigger, tougher challenge than this one. There are time limits on the swim, bike and run portions and you will need to have a serious amount of previous race experience to even think of entering this one. Just the thought of having to swim 38km within 25 hours is enough to scare the hind legs off a donkey let alone worrying about the bike and run disciplines.

This one is only for the most insane, brave and a little “touched” triathlete out there – BEWARE, you have been warned but the bragging rights once you earn that finishers t-shirt should get you free drinks offers for life.

2. The Australian ULTRAMAN

You can look at this as the “baby” to the Swiss Ultra Deca tri. Considering the fact that you only have to swim 10km, bike 421.1km and run 84.3km. It’s a heck of a lot shorter than the Deca but man oh man! It’s going to hurt and be a huge challenge for even the most hardened triathletes out there.

Try swimming 10km and cycling 140km on Day 1. Then follow that up with a 281.1km cycle on Day 2, and finally finish off with an 84.3km run on Day 3.

Just reading through the guidelines will be enough to give you heart palpitations, let alone actually get out there and doing the business. A race distance that totals over 500km would certainly be classed as the most challenging. Consider this as a curtain-raiser to the DECA.

3. The Patagonman

It does start to get somewhat easier with the Patagonman that takes place in Chile normally during the month of December. You only have to swim 3.8km, then cycle 180km with a 42km marathon leg to end it all. Sounds easy? Maybe not so easy. The water temperature for starters will be around 12 degrees.

The longer you take to swim, the colder you shall become. The cycle route then runs itself into the Andes mountain range while the run is completely off-road. They mention ice-fields, glaciers and rugged mountains on the website basically tell you that it’s not going to be easy – no sugar coating with this race organisation – if they say it’s going to be tough, expect it to be even tougher.

This may sound like something that could appeal to a vast array of athletes, especially the adventurous ones. However, make no mistake to underestimate the challenge. You will have to be up for the challenge in more ways than one, plus the scenery will knock the socks off anything out there.

We rate a holiday trip over to Chile with a race event thrown in to complete the package is the way to go. With the event being hosted in December, it’s an ideal getaway time that you will never forget once you cross that finish line.

4. The Escape from Alcatraz Triathlon

Finally, The Escape from Alcatraz Triathlon that has been staged in San Francisco USA since the start of the eighties. This forms part of many triathlete’s bucket list due to its challenging appeal. Apart from its iconic status, the challenge of diving off a ferry into ice-cold waters and then having to contend with exceptionally strong currents will make this “short” distance triathlon a real challenge for most.

The vast majority of triathletes tend to battle with the swim. A swim of this nature will put the fear into the weaker swimmer before they have even started the race. The swim is 1.5 miles in length (around 2.4km if you swim straight and judge the current correctly). The cold water will be a huge challenge as there is no warm-up – off the ferry, into the water and you better start swimming hard and fast.

The bike is 18 miles in length (less than 30km). The short, sharp, and steep hills will be enough to work the quads over in a big way. Make sure your bike is prepped and serviced with the brakes working 100%. This might be THE race where the all-new rage of using a disc-brake bike becomes advisable. The run is relatively short at 8 miles long (just short of 13km) but it includes the infamous Sand Ladder near the end of the run which is a 400 stair climb from the beach back onto the top road as triathletes make their way to the finish chute. This is the most challenging triathlon event that we should all aspire to do someday.

Can I achieve a finish as these challenging triathlon events?

Yes of course, why not. You may be a total newbie but who says you cannot aspire and achieve a finish at every one of these events listed above. Some handy tips to keep in mind are:

1. You need to build-up to the challenge

Earn your stripes so to speak. Start with short distances and slowly progress up the ranks to longer and more challenging events.

2. You will need to be physically fit of course

But don't forget to train yourself mentally to compete at these respective events. Developing a mentally strong mentality takes time to develop and only once you have completed a good few races prior to these can help you build up the necessary mental strength to even consider taking on the challenge.

3. You might need some extra money

 As we know, some triathlon entry fee’s these days are not cheap and the planning and travelling that may be involved in taking up one of these challenges will be a challenge on its own. If the desire is there and strong enough, the drive to ensure you find the finances will easily follow.

4. Plan well in advance

You will need to set the travel plans well in advance followed very closely by the training plans. This type of challenge easily spans a good few years for some, so make sure when you click that entry submit button, you have the necessary short and long-term plans in place.

5. You will need to be adventurous and willing to try something different

Most of your friends and training mates will generally stick to what they know and are comfortable with. A race challenge of this variety will require you to step outside of the comfort zone and perhaps enforce you to go it alone. This is where mental strength will kick in. The rewards at the end will be so much sweeter if you are willing to commit when no-one else will.