12 Fun Monthly Running Challenges

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Do you want to supercharge your running life whilst having lots of fun at the same time?

You might think this is too good to be true. Having fun whilst training to up my running game? How could that possibly be fun? With fun challenges!

Why take on running challenges?

Grow as a runner
We’ve all heard that phrase William S. Burroughs once said ‘when you stop growing, you start dying‘. Absolutely true in all wakes of life and running is no different.

By definition, a challenge is a task or situation that tests someone’s abilities and helps them grow. By taking on running challenges you will not only explore your current ability but you will push yourself to the limit and become a greater runner in the process.

A sense of achievement
We humans like to feel that we are special. That we can perform a task to a high standard. We admire achievement and strive to achieve ourselves.

When we watch the Olympics, the premier league or a sports championship, we can’t help but feel a sense of awe and respect towards the sportspeople for their physical performance and mastery of their sport. The same is true for challenges in our lives.

When there is a standard to be met, a goal to strive for, something to achieve, we pursue it until we are successful. Think of a promotion at work, learning a new song on the piano, learning new language vocabulary, loving our spouse and so on. We’re driven by a need to accomplish and fun running challenges can give us a sense of accomplishment.

Boosting self-esteem

Self-esteem is how we value and perceive ourselves. It’s based on our opinions and beliefs about our self and what we think we are worth. People with high self-esteem tend to be confident, happy and daring whilst those with low self-esteem tend to be sad, unassertive and lack daring behaviour. I believe completing challenges in life (like these running challenges) helps to develop a sense of self-esteem, giving you access to a higher quality existence.

Dan Pena once said ‘high self-esteem gives you the power of confidence to take chances.’ People who love themselves are more likely to take risks and live their life to the full compared to low self-esteem individuals. You could say the secret to a happy life is high self-esteem. Something which can be developed by pursuing and overcoming running challenges.

Running challenges are powerful because your results can be measured. This means it’s easy for you to see if you have accomplished what you set out to accomplish. For instance, running a certain distance in one month or beating a personal best are both measurable goals you either beat or you don’t. You know if you’ve succeeded or if you’ve failed. This is extremely powerful for building self-esteem as there is no confusion as to whether you have done well or not. You will know by the results you achieve, whether you overcome the challenge or not.

Build your self-esteem by accepting and smashing these monthly running challenges. I dare you!

In this article, you’ll get one fun running challenge per month to keep your running testing but fun. Enjoy and embrace as many challenges as you can.


1. Run every day for a month

Objective: Build consistency, become familiar with running, get comfortable with your style.

Building a running streak of 30 consecutive days is a fantastic challenge you can embrace at the start of the month. Run at least 1 mile (preferably a minimum of 3) each and every day, regardless of weather or how you feel, and you will complete the challenge.

Why is this challenge worth doing?

Consistency is incredibly important for running success. This challenge will build your self-discipline to run, even on days and in moments when you simply do not feel like it.

Think about top performers in the sport. Mo Farah, Paul Martelletti, Laura Muir. All of these successful runners all have one thing in common with their training. They are consistent and disciplined to always show up and run, even on days they do not feel like it.

Whilst you might not strive to be an Olympic running champion, the lessons you learn by achieving this challenge will transfer to other areas in your life and you will be a more successful person. You’ll be disciplined to read more, show up for work even when you’re ill, always put in effort with your spouses, clean the house regularly.

Running everyday for a month is a fun challenge to undertake with benefits to your sporting performance and in other areas of your life. Be sure to use a sports watch to log each run you do on a running app, like Strava, to prove to yourself that you are doing it.

2. Run 100 miles in one month

Objective: Increase your endurance, achieve a target, build self-esteem

Setting and achieving the goal of 100 miles in one month is a fun challenge to get involved with. Try and average at around 25 miles each week and you will smash this goal and become a better runner in the process.

Why is this challenge worth doing?

Something all runners can deal with is improved endurance. It doesn’t matter if you’re a fast 5K runner or a marathoner, you will need good physical fitness to perform to a high standard.

If you run a 5K with a low monthly mileage (say 18 miles), you will get tired by mile 2 and have a slump towards the end of the race. Likewise, if you attempt a marathon on a low monthly mileage (25 miles) then you will fatigue extremely quickly and have a bad time. If you have a decent foundation of physical endurance from running further each month, you will be able to sustain performance for longer time periods and run much better. Just one reason to book yourself onto this challenge.

An added benefit of completing the 100 mile month challenge is building self-esteem. Our self-esteem is our opinion of our self. If you set and achieve difficult challenges for yourself, like the 100 mile month challenge, you will have a powerful reference for something you have achieved. Suddenly, you have faith in your ability to perform and will value yourself more highly.

Having a high self-esteem transfers to other areas in your life like in your career, relationships, playing with your kids, socialising, playing a musical instrument and so on. Do not underestimate the power of building self-esteem from challenges like the 100 mile month running challenge.

3. Climb 3000 feet in elevation gain in one month

Objective: Improve fitness, hone form, blitz hills during races

Leave the flats behind and climb at least 3000 feet in elevation gain in one month of running. This may seem daunting at first, especially for a runner more accustomed to flat ground. You will soon see that adding hills to your workouts will supercharge your running life, hence it is a game-changing challenge to take on.

Record your runs using the app ‘Strava’ to track how high you are climbing on your runs. As soon as you reach 3000 feet, the challenge is complete and you can feel like you’ve mastered the slopes. Remember to spread the climbing across lots of runs throughout the month as trying to do loads of climbing in one run can risk injury, burning out or even feeling faint and light headed.

Why is this challenge worth doing?

Running up a hill is much more physically demanding than flat-ground. This means you burn more calories and become fitter from regularly doing hill workouts. If you’ve ever gone hiking you know a sweat is worked up from climbing hills rather than walking on flat surfaces.

It’s harder to run uphill because it means you must lift your body weight upwards, requiring greater energy, which is why our muscles feel tired quicker going uphill. Take on and crush this 3000 feet month running challenge and you will notice your fitness skyrocket. Your only regret will be that you didn’t start doing hill workouts sooner.

An added benefit of hill running is you will blitz hills others consider difficult during races. One of my most bizarre race memories is running up a steep category 4 hill whilst everyone around me slowed to a walk. I raced past fellow runners feeling confused. How was I managing to run so easily whilst everyone else struggled? Then it hit me. I had added hill workouts to my training regime and made a big deal of racking up lots of monthly elevation gain during training. It really pays off during races. If you want to blitz race course hills others find difficult, take on this challenge and discover what hill workouts can do for you.

For more information on hill running check out the following blog post:

4. Participate in four running events in one month

Objective: Have fun, enjoy competition, achieve personal bests

Running events are organised races which have a clear start and finish line. Events come in all shapes and sizes and include marathons, half-marathons, 5Ks, fun runs, fancy dress runs, paint runs and so on. What kind of events you participate in is down to personal preference but the main thing about this challenge is doing one each week for a month.

An easy way to force yourself to complete this challenge is to sit down at your computer, find and book all four events in one go. Once you’ve paid the money you will have committed in your mind. Nobody likes missing out on an event they have paid their hard earned money for, so paying for them in one go will make you commit to the challenge.

Why is this challenge worth doing?

This challenge is all about getting involved in some running events and having fun. If you’re a new runner, you probably aren’t aware how much fun the sport can be. Not only is it fun to train alone, as a solo effort, but it’s even more fun to apply your training to participation at events. Once you get your feet wet with your first few events, you will likely catch (if you haven’t already done so) the running bug and feel inspired to make running an integral part of your life.

Another benefit of doing events is enjoying friendly competition. Running with others in timed races means your performance will be placed on a leader board. Suddenly, there are runners who are faster and slower than you which can act as a great incentive to perform better in the event.

If you can beat other runners and get a personal best for a set distance, why not? If you’re a competitive person, try and place as close to the front as possible and try to get a personal best. Whilst this challenge isn’t about killing yourself with physical exertion and having a ‘win or die’ mentality, it’s all about learning how much fun competing in events can be.

Participation in events can spark a passionate love-affair with running and is a fantastic way to enjoy the sport more. Take on the challenge and smash it. Participate in four events across one calendar month.

For more information on participating in running events check out the following blog posts:

5. Wake up and start running before 6:00AM 4 days a week

Objective: Create momentum, build discipline, appreciate mornings

Something I swear by is getting up early and running first thing in the morning. David Goggins, of my greatest role models, said in a podcast that running first thing in the morning means winning the first battle of the day and creating positive momentum.

Saying this to somebody who doesn’t run first thing will be a bit sceptical, but coming from somebody who runs before 6:00AM every morning I can testify this is the absolute truth.

Why is doing this challenge worth it?

Running first thing, before everyone else is awake, has changed my life in an amazing way and I would recommend it to anyone. That is why I advise you take on this monthly running challenge. Try waking up and running before 6:00AM 4 days a week and reap up all the benefits.

If you run first thing, you start the day having already accomplished something and you have positive momentum. You’ll feel more energised, motivated and ready to take on tasks & challenges as they appear.

Another benefit of running first thing in the morning is building tremendous self-discipline. It can be difficult to beat the snooze button and get out of a nice warm bed for running through a cold, wet morning. But if you can beat the alarm time and time again you will build huge self-discipline and will get up to the first alarm no matter what. This is fantastic for building self-discipline which can transfer to other areas of life like in business, with relationships, academia and so on.

One of the best things about early running is building an appreciation of mornings. Running at the crack of dawn means there is less traffic and pedestrians about, birds begin singing and you have a lot of time to yourself. It won’t be long before you start associating early running with peace, relaxation and a newfound respect for the mornings.

Take on and smash this challenge for a more fulfilled running life. This might be one of the most difficult challenges on the list but I promise it will change your life if you succeed and continue running early afterwards.

For more information on morning running check out the following blog post:

6. Achieve a negative split on 4 weekly long runs in a row

Objective: Improve mental toughness, increase your endurance, achieve faster running

A negative split is a racing strategy that involves completing the second half of a race faster than the first half. It is defined by the intentional setting of a slower initial pace, followed by a gradual or sudden increase of speed towards the end of the race.

Why is doing this challenge worth it?

If you achieve a negative split during a long run this means you are able to push harder even though you are already tired from the first half of your workout. Runners who can achieve negative splits on long runs tend to have more mental toughness as they can push through pain. Mental toughness is a great trait for runners to possess, especially during a competitive race.

Negative splits tend to mean faster race times. Starting slower than you’re capable of means introducing your body to physical activity gradually so it is not overwhelmed by the fatigue of running extremely quick straight off the start line. Once the blood is flowing and you’ve warmed up, you will know what you are currently capable of and can run at a pace which suits your ability during the race. If you’re feeling really good, run as fast as you can. Go for it, why not? A negative split strategy tends to mean faster times and it is my personal favourite strategy for running faster.

7. Set a new mile personal best

Objective: Build speed, refine form, achieve a goal

Setting a new mile personal best is all about speed and proper form. So, how fast is fast? Roger Bannister was the first person to run a mile in under 4 minutes. You don’t have to aim for a target this quick but it gives you an idea of what is possible.

A good starting point is knowing what your current mile personal best is and setting out to beat it. If you don’t know, that’s fine. Run a mile as quick as you can at the start of the month, record your time and compare it to your time at the end of the month. More than often, runners are staggered at how much progress is possible in one month.

My current mile personal best is 5:45, what’s yours? Whatever it is, vow you will smash it this month. I have beaten my mile record, time and time again, during a parkrun race as the competitive nature within me strives to beat as many runners as I can which explains my fast mile times.

Maybe your best place to set a new mile personal best is on an athletics track or alone at the crack of dawn. Whatever works for you, get out and beat your mile personal best this month.

Why is this challenge worth doing?

Running your fastest mile will improve both your speed and form. Naturally, you will need to do some speed workouts – like fartlek or interval training – to build a quicker pace which will make you a faster runner. Why is being faster better? You can get better times, burn more calories and enjoy the sport more!

To achieve a faster mile, you will need to refine your running form. This is a fantastic opportunity to learn about applying proper technique so you move as efficiently as possible. Watch the following YouTube video for some guidance.

8. Complete the 4/4/48 running challenge

Objective: Build mental toughness, develop stamina, build self-esteem, have thinking time

What is the 4/4/48 running challenge?
The 4/4/48 running challenge requires you to run 4 miles, every 4 hours, for 48 hours. I first learned of the challenge when David Goggins, a tough ex-Navy Seal, made billionaire Jesse Itzler do it in the book ‘Living With A Seal‘. Out of the many workouts in the book, Jesse Itzler describes this one as the hardest.

Why is the 4/4/48 running challenge difficult?
At first, the idea of running 4 miles, every 4 hours, across 48 hours seems easy. For those who run regularly, 4 miles isn’t a huge distance. However, the number of times 4 miles is required across a 48-hour span quickly begins to seem like torture as those undertaking the challenge clock up almost 50 miles. That’s nearly 2 whole marathons in 2 days.

Why is doing the challenge worth it?

This may be one of the hardest running challenges there is but the benefits of completing it are huge.

You will develop mental toughness from running every four hours, regardless of how tired or uncomfortable you are. If you’re tired at 2:00 AM and it’s cold, raining & windy outside, you still have to run the 4 miles to ensure you complete the challenge. Through overcoming the difficulties in this challenge, you’ll realise you’re tougher than you think. Moving forward after completing the challenge, you’ll have tremendous self-confidence in your abilities.

An added benefit of doing the challenge is having time to think. The challenge provides lots of opportunities, like in the night, to run on your own and have some thinking time. In the modern world, quiet thinking time is hard to come by due to all the distractions like social media, our careers, families etc.

Completing the 4/4/48 challenge will remind you just how valuable quiet thinking time is for understanding where you are in life, what you need to do moving forward and for a general sense of relaxation.

It’s a huge challenge but I promise it will be worth it. Make the month one to remember and complete the 4/4/48 running challenge.

For more information on the 4/4/48 challenge check out the following post:

9. Listen to 3 audiobooks whilst running in 1 month

Objective: Increase knowledge, reduce stress, improve focus, enjoy running

This month is a bit more relaxed than the others and it focuses on audiobooks. Something which has changed my life for the better is listening to audiobooks during long runs.

What’s an audiobook?
An audiobook is exactly what it sounds like. A recording of somebody reading a book which you can listen to instead of reading. For example, an audiobook of The Great Gatsby by F.Scott Fitzgerald will be a word for word reading of the text by a professional audiobook reader. Instead of reading the words, you listen to the words.

How can I listen to audiobooks whilst I run?
You can download audiobooks onto your phone using apps like Audible, Google Play Books & Librivox. Simply download them, put some earphones in, click play, run and lose yourself in the book content.

Why is doing this challenge worth it?
The benefits of listening to absorbing content in audiobooks whilst you run are astronomical.

Listening to audiobooks increases your knowledge base, making you a smarter person. Having more knowledge can change your life for the better. It’s like the billionaire Warren Buffet says ‘the more you learn, the more you earn’. I’m not just talking about financial gain but also spiritual, romantic and fulfilment gain too.

Audiobooks can help you relax. There’s nothing quite like losing yourself in a good book. Whether you’re on the Pequod in Moby Dick, the workhouse in Oliver Twist or standing with Dorian Grey in the Picture of Dorian Grey, books transport you to another world. They have the power to take your mind off worries in life and allow you to relax. Some of the best moments in my running life have come from losing myself in a fictional world whilst coasting at a casual pace.

Audiobooks can improve your focus. In the modern world, there are thousands of things fighting for our attention every second of the day. Advertisements, social media, the radio, family, friends, work and so on. It can be difficult to switch everything else out and focus on one or two things at a time. If you’re unable to focus, you will not be able to undertake a project and see it through to the end. Even if you do complete it, it will likely be done to a poor standard unless you were able to focus.

Give it a try. Listen to 3 audiobooks whilst you run this month. With all the above benefits, it’d be crazy not to!

For more information on running with audiobooks check out the following blog post:

10. Run a marathon

Objective: Achievement, improve endurance, raise money for charity

Running a marathon is one of the most common items found on people’s life bucket list. It should be on yours too!

Why is doing this challenge worth it?

There’s something special about taking on and conquering the incredible feat of running 26.2 miles in one go. To some, running a marathon seems mad. Why on earth would anyone want to run this far, after all? Because it gives you a huge sense of achievement.

Marathoners get a special feeling inside once they cross the finish line. It’s like climbing a mountain and finally reaching the top. You have a moment of absolute gratitude for seeing it through to the end, not quitting and believing in yourself. It’s one of the best feelings in the world, which is why this monthly challenge is to run a marathon.

If you’re a charitable person, you could represent and raise funds for a charity during the marathon build up. You can pick any charity in the world so make sure you go for one you’re passionate about. I personally always raise funds for Parkinson’s UK, a charity I am incredibly passionate about. I admire the work Parkinson’s UK do and I am proud to wear the Parkinson’s UK shirt whenever I can during training & competition.

Pick a charity and fund raise during your marathon effort. Charity gives you a sense of fulfilment and well being you just can’t get any other way.

Run a marathon this month. It may seem daunting and unrealistic but I promise you that it’s possible. Believe in yourself, rise to the challenge and smash it out of the water.

11. Run a sub 20 minute 5K

Objective: Build speed, build stamina, refine race strategy, have fun

A common goal for many runners is to achieve a sub 20 minute 5K. 20 minutes is a nice round number to strive for and it will require running a pace of 6:25 per mile or quicker. Whilst this sounds fast to some runners, it is achievable if you implement the right kind of changes to your training routine.

Make sure you stay hydrated, try and race with a negative split, complete speed workouts, vary your training distance and refine running form. If you do all of these, you will stand a good chance of hitting a sub-20 minute 5K.

Why is doing this challenge worth it?

Achieving this challenge will give you a huge sense of accomplishment. Running a sub-20 minute 5K will prove you are well and truly on the road to being a successful runner and your self-esteem will increase too.

Your running form will have naturally improved as achieving this kind of time will require efficient body movement. Not only does proper running form make you a quicker runner, but it also limits the risk of injuries so you will be somewhat safeguarded from injuring yourself and being out of action for a few weeks.

I personally think the best place to go for a sub-20 5K is at a parkrun event. You will be properly timed, have friendly competition to push you and be in race mode rather than training mode. All helpful factors for running the fastest 5K you possibly can. Best of luck and I will hopefully see you on the other side of the sub-20 minute 5K.

For more information on running faster, check out the following blog post:

12. Run 50% of your monthly miles on a trail

Trail running means running on unpaved surfaces (not roads), often with steep inclines and in nature. Examples of trails include mountains, forests, woods, desserts and so on.

Objective: Build muscle, improve fitness, enjoy nature

As runners, we can become too comfortable with running on paved surfaces, like roads. Whilst road running is good, it’s beneficial to go back to basics and embrace the freedom of a trail. As it turns out, we’re actually built for trail running.

Rewind back to our evolutionary ancestors and remember humans were built for trail running. It wouldn’t be uncommon for our primal counterparts to run 10K every day to find shelter, food for survival. There were no roads or pavements but lots of woodland and mountains to pace through.

Why not reconnect with your primal side and get down and dirty on the trail for 50% of this month’s miles? Give it a try!

Why is doing this challenge worth it?

Trail running is fantastic for building up your leg muscles and improving fitness. The uneven terrain means your body legs and body are constantly adapting to their surroundings, expending more energy to get you through the trail. Pressure is put on different leg muscles and more effort is required to push your body up and down the trail, meaning your leg muscles get stronger and you improve your overall fitness.

Trail running also benefits your sense of balance and co-ordination. Uneven ground, rocks, roots and sticks are all challenges you need overcome while trail running so your continually improving your sense of balance and coordination.

You will get to know your body more, understand how it works under pressure and be in a strong position to negotiate tricky runs in the future (like a race) thanks to this knowledge of yourself gained from trail running.

Some runners don’t like the idea of the trail as it can be dirty, gritty and raw. Whatever your thoughts to trail running, give this challenge a go anyway. Most runners start trail running then find it becomes one of their passions in the sport. Soon enough, trail running is a part of their weekly routine and they regret not adding it to their workouts earlier.

What are you waiting for? Accept and smash this challenge. Make 50% of this month’s miles on the trail.

For more information on trail running, check out the following blog post:

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