Rob Roy Challenge

An epic hiking and cycling challenge through the Scottish Highlands, requiring all the courage, stamina, and determination of Scotland’s infamous outlaw, Rob Roy MacGregor

What is it?

An event that’s certainly not for the faint hearted, participants in the famous Rob Roy Challenge will need to really dig deep if they’re to overcome one of Scotland’s most gruelling events.

The Challenge raises funds for charitable organisations such as Mercy Ships, Breast Cancer Now, and Marie Curie. Those taking part will push with all their might along the 16 mile Rob Roy Trail, a long-distance path which stretches from  Pitlochry to Drymen, and which retraces the footsteps once taken by the infamous folk hero, Rob Roy MacGregor himself.

Sounds challenging? That’s just for starters.

The event is a combination of 4 challenges – Whilst those on the Rob Roy Ramble can put their feet up once they reach Kenmore, those looking to really push themselves to the limits can hop on their bicycles and continue on with one of three additional testing challenges – MacGregor’s Leap, Big Red or Schiehallion’s Shadow – consisting of cycle rides ranging from 15 miles to a demanding 56 mile route which climbs out of the shadow of the mighty Schiehallion mountain.

Where is it?

The Rob Roy Challenge starts in the town of Pitlochry, with the hiking part finishing at the end of the 16 mile Rob Roy Way in Kenmore. Meanwhile, cyclists taking one of the bigger challenges will see their levels of endurance tested as they ride through ancient villages like Fortingall, pass the legendary Black Wood of Rannoch, and traverse the hillsides in neighbouring Loch Tay, with all cycle events starting and ending at the Kenmore hub.

Guests staying at the Dunalastair Hotel Suites for this annual event will be no more than a 40 minute drive from the starting line in Pitlochry, or from the Kenmore finish line.

When is it?

The 2019 challenge took place this past June, and saw one of the biggest turnouts yet as scores of participants and supporters raised huge sums for the event’s chosen charities. For more information or to register, visit

Prefer something a little less daunting on your next Highland break? Enjoy a Scottish adventure holiday with cycling, hiking, and more at the Dunalastair Hotel Suites. Book your stay online today, or call our team now on +44 (0)1882 580444