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 first challenge is:

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.

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.