25 Great Outdoor Challenges

Two people kayaking during the Rat Race Coast To Coast Adventure Race
(Image credit: Rat Race)

Had enough of beach holidays and city breaks? Whether you’re looking for a one-day activity or want to spend weeks on a serious test of your fitness, there’s something for you in this list of extreme (and not-so-extreme) challenges.

With a little training – or in some cases no training at all – everyone will be able to tackle the beginner challenges on the list, but if you fancy one of the advanced or extreme challenges then it’s going to take some serious preparation and, in the case of the extreme adventures, probably a fair chunk of your annual leave. Whichever challenge you opt for, however, you can be sure you’ll have a great experience and undoubtedly get a little fitter at the same time.

Beginner Outdoor Challenges

1. Cycle Up Bealach Na Bà

This winding mountain road in the Applecross Peninsula in north-west Scotland is the biggest climb you’ll find on British shores, ascending 626m from sea level over the course of just 9km. It’s scored as 11/10 in terms of difficulty in 100 Greatest Cycling Climbs by Simon Warren, the only rating above 10 on Warren’s list of the toughest British ascents. In short, it’s a challenge that should be on every cyclist’s bucket list, perhaps as part of the annual 145km Bealach Mor sportivecyclinguphill.com/100-climbs/bealach-na-ba/

2. Swim From Nevis To St Kitts

The Narrows is the strait between the islands of Nevis and St Kitts in the Caribbean and every year a couple of hundred people swim the 4km of open water between Oualie Beach on Nevis and Cockleshell Beach on St Kitts as part of an organised event. Taking on that distance in the sea is no small feat and beginners are encouraged to use training fins to make it easier, but it’s a truly beautiful stretch of water to be in, and getting to spend time on a Caribbean island before and after is no great hardship either. nevistostkittscrosschannelswim.com

3. Finally Learn How To Surf

Surfing should be great fun, but in reality you’ll often spend most of your time waiting about, missing good waves and then getting unceremoniously dumped in the wash when one does finally arrive. The multi-million pound Adventure Parc Snowdonia is home to the world’s first artificial inland surfing lagoon, consistently churning out perfect rides that run for 150m. We had always struggled to stand up on a board, let alone make it to the end of the wave, but managed it in an hour or so here. Highly recommended. adventureparcsnowdonia.com

4. Rough It In The Woods

He might be a tad more familiar with hotels than he originally let on, but Bear Grylls still knows his survival stuff. These hands-on courses, designed by the man himself, range from an overnight adventure in the South Downs to a five-day survival course in the Scottish Highlands, including a self-rescue survival challenge. beargryllssurvivalacademy.com

5. Reach New Heights In Germany

Indoor climbing is a brilliant way to keep fit, but nothing beats heading out and doing it for real. The world-famous spot Frankenjura in Bavaria has over 8,000 established routes, including nearly 300 graded for beginners. There are a variety of route lengths, so there’s something for everyone in this land of limestone crags and picture-perfect forests. climb-europe.com

6. Go White-Water Rafting

You don’t have to head Down Under to get the thrill of hurtling along on an inflatable dinghy – but the Tully River in Cairns, Australia, is regarded as the best place in the world to give it a go. It encompasses 44 rapids winding through a World Heritage rainforest, complete with huge waterfalls and dramatic gorges, nearly all of which are suitable for people who’ve never even picked up a paddle before. raft.com.au

7. Take The Bull By The Horns

As far as physical challenges to tick off the manly bucket list go, this takes some topping. The Rodeo Bull Riding School in Houston, Texas, is run by one of the world’s best rodeo cowboys and promises to teach you all aspects of the sport, before letting you loose on the real thing. We can’t find anything on its site that states we definitely won’t get gored, though. Reassuring… greatamericandays.com

8. Swim Between Two Castles

The RNLI Castle 2 Castle Swim sees 450 swimmers (and no more, so don’t delay your entry) complete a one-mile (1.6km) open-water swim across the Carrick Roads estuary in Cornwall. The two castles in questions are Pendennis Castle in Falmouth, where the event starts, and St Mawes Castle on the Roseland Peninsula. The event boasts a fun and friendly atmosphere, and costs £25 to enter, though you’re also expected to raise at least £50 for the RNLI. eventbrite.co.uk/e/rnli-castle-to-castle-swim-2023-registration

Advanced Outdoor Challenges

9. Complete George Fisher’s Tea Round

George Fisher’s Tea Round

(Image credit: George Fisher)

Named after the George Fisher store it starts and finishes at, this 30-mile (48.2km) route around the Lake District involves summiting the 10 fells you can see from the top floor of the store, climbing almost 12,000ft (3,657m) in the process. You can run or walk the route either clockwise or anti-clockwise, and finishers are rewarded with some goodies from Montane, which sponsors the Tea Round, and a cup of tea and a slice of cake in the George Fisher store. georgefisher.co.uk/pages/george-fishers-tea-round

10. Take On Ten Y Fan

A true test of anyone’s mettle taxes mind as well as matter and this climbing challenge places both your body and brain under significant stress. If you know your Welsh mountains, you will have already guessed what this challenge entails. For everyone else, it’s climbing Pen Y Fan ten times. In 24 hours. The 886m Brecon Beacons peak is the highest in south Wales but it’s not exactly K2, so your first climb may very well be a breeze – but it will only get trickier. You’ll have to cope with the tempestuous Welsh weather as well as the setting of the sun (providing there is any). Take extra care to follow the safest route, but one that allows you to reach the summit in sufficient time. 10yfan.com

11. Swim A 10K

The UK’s first open water 10K event, The Dart, is an incredible journey down south Devon’s Dart estuary. Making your way along a river with 1,600 other swimmers is an experience like no other. And because this isn’t a race (everyone takes it at their own speed), you don’t need to worry about getting accidentally kicked in the face or swum over by screw-faced competitors. outdoorswimmingsociety.com/dart-10k

12. Go Heliskiing Or Heliboarding

Getting taken up a mountain by helicopter isn’t just a fancy way to skip the ski-lift queues. You’ll get dropped off in pristine, untouched powder before making your way down on a route untouched by anyone else that day. It’s not just for 80mph black run bombers, either – in Whistler, Canada, while there are trips for gnarly adrenaline junkies, total powder novices are catered for too. whistlerheliskiing.com

13. Race The Scotland Coast To Coast

Rat Race C2C adventure race

(Image credit: Rat Race)

Use your feet, pedals and paddles for 169km as you run, cycle and kayak from one side of Scotland – which is certainly not the world’s flattest country – to the other. The race starts at Nairn on the east coast and heads south west to the finish past Fort William, taking in Loch Ness along the way. It’s a two-day event, although the brave (and exceptionally well prepared) can attempt it in one day. ratracecoasttocoast.co.uk

14. Escape From Alcatraz

In its 29 years as the world’s most infamous maximum-security prison, no-one ever escaped alive from the shores of Alcatraz. Now, each June, 2,000 of the world’s best triathletes assemble in San Francisco to try. To be fair, security isn’t what it was, but this triathlon with a brilliant novelty factor is still a gruelling affair. A 2.4km swim through frigid waters from Alcatraz Island to shore is followed by a 29km bike leg, then a 13km run through the rugged trails of Golden Gate Recreation Area. Set against the famous skyline of San Francisco, it’s little wonder the event draws over 20,000 spectators. escapealcatraztri.com

15. Cycle Mont Ventoux’s Three Ascents

Lance Armstrong called Mont Ventoux “the hardest climb in the Tour de France”. But the Tour only ascends it once – the real challenge is to cycle up all the mountain routes in a day, racking up a Herculean 4,443m of ascent and 68km. You can face winds of 100km/h or more near the summit. cycling-challenge.com

16. Learn To Kitesurf


(Image credit: Adam Hughes)

One big, fat, undiluted serving of adrenaline, this. You can learn to harness wind power on the water pretty much anywhere these days, and KiteWorldWide offers package holidays with lessons all over the world – in Greece and Italy but also Cape Verde and Panama. Blow as much of your holiday time on it as you can, because it’s not especially easy to pick it up, but once you do, hoo boy, you’ll feel like you’re flying. kiteworldwide.com

17. Ice Climb Ben Nevis in Winter

Britain’s highest summit is a straightforward hike in normal conditions – but in winter, covered in ice and snow, it’s a different beast. There are routes of all lengths and difficulties; make sure you have the necessary skills or go with an experienced guide. visitfortwilliam.co.uk

18. Cycle Across England

Around 13,000 people cycle coast to coast in England each year – the challenge is to complete the C2C route in a weekend. The traditional route starts at Whitehaven on the west coast and ends at Tynemouth, taking in the Lake District. Most of the route is quiet country roads, cycle paths and off-road trails, so there’s plenty of scope to let loose. Going west to east takes advantage of prevailing winds, as well as short uphills and long downhills. sustrans.org.uk/c2c-or-sea-to-sea

Extreme Outdoor Challenges

19. Run Britannia

Run Britannia

(Image credit: Run Britannia)

This challenge certainly falls into the extreme category, so much so that you’re getting more than two years’ notice about it so you have adequate time to prepare if it does tickle your fancy. Run Britannia 2025 takes place in June and involves running the length of Britain, completing a 1,000-mile (1,609km) route from Land’s End to John o’Groats. The event is organised by Rat Race, which has picked out a runner-friendly route that avoids the biggest roads and includes some of the country’s most scenic walking trails, although that does mean you’ll be racking up 70,000ft (21,336m) of ascent along the way. 

There are only 40 spots available in the challenge, and the 2023 event sold out in less than six hours, so if you are keen to take on Run Britannia in 2025, it’s worth signing up to be notified when places are available. One last thing to note is that it’s a very expensive event at £7,950, but you can use the ample prep time to do some saving. ratracerunbritannia.com 

20. Walk The South West Coast Path

The Pennine Way may be more remote and muddier, but the South West Coast Path is England’s longest National Trail. The 1,014km route starts in Minehead, Somerset, and follows the wild coast around Devon and Cornwall into Dorset, finishing in Poole. To walk it in one go you’ll need a couple of months, but you can tackle its tough ascents one at a time for a satisfying hike. While the coastal weather doesn’t always smile on walkers, the scenery is outstanding – the path has sections designated Area of Outstanding Natural Beauty, Heritage Coast and World Heritage Site. southwestcoastpath.com

21. Race The Ironman 70.3 Aix-en-Provence

The idea of a half Ironman is much less intimidating if you take part in one somewhere bright and sunny rather than grey and gloomy. The Ironman 70.3 Pays d’Aix – a qualifying race for the Ironman 70.3 world championship – takes place in the city of Aix-en-Provence, which apart from its promise of sunshine has a reputation as a training mecca for French cyclists and triathletes. Competitors swim 1.9km, cycle 90km and run 21km, with the bike ride the most challenging part and not just because of the distance. The course includes the famous mountain pass in Provence, around Mont Sainte-Victoire, immortalised by the painter Paul Cézanne. The road isn’t in good condition and there are some long, torturous ascents. ironman.com/im703-aix-en-provence

22. Run The Ultra Trail du Mont Blanc

Why? It’s simply the most challenging foot race in Europe. The 166km trail loops the Mont Blanc Massif, with a total height gain of 9,500m. Competitors must carry all their requirements and while super-athletes finish in around 20 hours, most runners take 30 to 45 hours – that’s if they finish at all. Shorter races and a team 300km are also available. ultratrailmb.com

23. Walk The Pennine Way

This is the classic long-distance trail in the UK. The record for the 431km stomp along the backbone of England is a maniacal two days, 13 hours and 35 minutes, although most mortals will take 16-19 days. The trail leads from Edale in the rugged Peak District through the Yorkshire Dales, along Hadrian’s Wall to the giant Cheviots and the Scottish border. Although notorious for foul weather and treacherous peat bogs, the Way has the wildest and best upland walking in England. It was too tough for arch-rambler Alfred Wainwright: “You won’t come across me anywhere along the Pennine Way,” he said. nationaltrail.co.uk

24. Paddle From Devizes To London

The Devizes Westminster International Canoe Marathon, the longest nonstop canoe race in the world, goes 200km from sleepy Wiltshire up the Thames to Westminster and requires about 30 hours of hard work. Training is essential to complete the race: “many ‘fit’ people have turned up to take part,” the organisers say, “but most collapse and fail within a few hours.” Paddling through the night, fighting exhaustion and mental fatigue, is a real test of fitness and character, and finishing in under 24 hours is seen as a good time. The intensity of training required is said to be the closest you can get to Olympic training. dwrace.co.uk

25. Run One Of The Big Three Rounds

The big three rounds are three epic ultramarathon-distance runs in the UK that take in some of the most challenging and breathtaking scenery the country has to offer. The most famous of them is the Bob Graham Round, which involves tackling 106km (66 miles) and 42 peaks in the Lake District, with more than 8,000m of climbing. The Paddy Buckley Round is set in Snowdonia and is 100km (62 miles) long with 47 summits and more than 8,500m of climbing. The Charlie Ramsay Round is in the Scottish Highlands and requires you to run 90km and climb 23 Munros, including Ben Nevis, for a total of more than 8,600m of ascent.

With each of the three rounds the challenge is to complete it in under 24 hours, which is a stern test for anyone. You can also adjust the challenge involved by going for it in different seasons, changing the direction you do the round in or, if you’re truly mad, by going for a double round and doing it twice.

If you can’t choose between which of the rounds you’d like to do, then you could always do all three. Inov-8 ambassador James Gibson did the trio in one winter, coming in under 24 hours for all three. Impressive.

More Adventures

Max Anderton

Max was the head of digital content for Men's Fitness which worked alongside Coach between 2015 and 2019.

With contributions from