The Challenge Series – Longer Walks & Bigger Adventures
There’s something special about setting out knowing you have a long journey ahead.
The Challenge Series is about going further, staying out longer and discovering what you’re capable of along the way. These walks aren’t about racing or reaching a summit — the challenge comes from distance, duration, changing terrain and the commitment needed to keep moving towards a destination.
And because this is Land & Legend, it’s never just about the kilometres. Along the way we’ll explore the history, heritage, landscapes and stories of the places we walk through.
Where We Walk
The Challenge Series will take us along some of Ireland’s great trails, historic routes, forests, valleys, coastlines and open countryside.
Some challenges will be big days on the trail. In time, others will take us further — including multi-day journeys, overnight adventures and walks incorporating both campsite and wild camping.
Our current challenges are:
Dublin Mountains Way Autumn Challenge – Saturday October 24th
From Tallaght to Shankill, we’ll take on the Dublin Mountains Way in one big autumn day — travelling from the edge of the city, through forests, open countryside and the Dublin Hills before eventually descending towards the coast at Shankill.
At approximately 42km, this is a genuine endurance challenge, but it’s not a race. We’ll walk together at a steady, purposeful pace with stops along the way, including complimentary refreshments at Glencullen Adventure Park.
There are also planned early exit options at Bohernabreena, Tibradden, Glencullen and Barnaslingan for anyone who decides they’ve had enough for one day.
For more information and booking options see here.
North Wicklow Triple Crown Challenge – Saturday November 21st
From Bray to Kilmacanogue, we'll take on the North Wicklow Triple Crown in one big day — climbing Bray Head, Little Sugar Loaf and Great Sugar Loaf, with spectacular views across the Irish Sea, Dublin Bay and the Wicklow Mountains along the way.
At approximately 18 km with nearly 1,000 metres of climbing, this is a Moderate to Difficult hike aimed at walkers with some experience who are ready to take things up a gear. It's not a race — we'll walk together at a steady, purposeful pace, with breaks to enjoy the scenery and discover the ancient quartzite geology linking these three distinctive peaks.
This is a public transport-friendly, point-to-point hike, starting in Bray with DART and bus connections and finishing in Kilmacanogue, where buses provide connections back to Bray.
For more information and booking options see here.
What to Expect
These walks are about challenging yourself while still enjoying the journey.
We’ll walk at a steady pace, but longer distances mean longer days and require a good level of fitness and preparation. Depending on the challenge, we may experience everything from woodland tracks and country lanes to rougher trails, changing weather and fading daylight.
Along the way, there’ll still be plenty of time for:
Local history and heritage
Stories connected to the landscape
Conversation and shared experiences
Rest and refreshment stops
Those moments when you realise just how far you’ve travelled under your own steam
Future challenges will vary considerably. Some may involve a single long day; others may eventually involve several days on the trail and carrying what we need for an overnight camp.
Safety & Planning
All Challenge Series walks are:
Carefully planned and risk assessed
Led by a qualified and experienced walking leader and National Tour Guide
Limited to manageable group sizes
Weather and conditions dependent
Every challenge will clearly set out the distance, expected duration, terrain, fitness requirements and equipment needed before you book.
These walks won’t be for everyone — and that’s rather the point.
Sometimes the best way to discover what you’re capable of is simply to keep walking.
Join us and take on your next challenge.