> Hillwalk Tours Blog > Hiking in Scotland > Rob Roy MacGregor: The Man, Myth and Legend
POSTED BY October 20, 2020

Rob Roy Macgregor

Rob Roy MacGregor was a man, is a legend but was never a myth.

He was an incredibly fascinating character in Scotland’s history.

What’s even more fascinating is the fact that you can follow in his cattle-droving footsteps along the Rob Roy Way.

Portrait of Rob Roy MacGregor

His tales became legendary through Sir Walter Scott’s novel, “Rob Roy”.

There were tales involving cattle-droving and (mild) extortion.

Stories about feuds with Dukes and Jacobite battles only added to his legend.

Even before that, he was a literal living legend as his exploits were detailed in a much exaggerated book called “The Highland Rogue”, which some believe was written by Daniel Defoe.

Many people don’t actually attribute Defoe with this work though.

So who was the real Rob Roy MacGregor?

Was he the outlawed, brutish highwayman that many might picture?

Was he the well-educated, highly-opinionated man that his written letters indicate?

The Beginnings of Rob Roy MacGregor

In 1671, a future legend was born in Glengyle on Loch Katrine.

His father, Donald, held the title of Lieutenant-Colonel for serving in King Charles II’s army.

He was also very loyal to the dynasty of the Stuarts and instilled this loyalty into Rob Roy as well.

A Statue of Rob Roy MacGregor

At the age of eighteen, Rob and his father joined the Jacobite rising, which aimed to reinstate James II to the throne of Great Britain.

In 1693, at twenty two, Rob Roy married Mary Helen MacGregor.

First Three Stages of the Walking Route

Drymen to Aberfoyle

The first stage of Rob Roy’s cattle droving path goes from Drymen to Aberfoyle.

During MacGregor’s era, the village of Drymen was on a popular drovers’ route meaning many people would use it as a stop-off point.

Due to its history, there are a lot of old buildings and ruins to visit such as Buchanan Castle and an old motte which dates back to medieval times.

Nowadays, the path to Aberfoyle is mainly along small, quiet roads and forest tracks.

Aberfoyle is a bustling little village, with interesting shops and great places to eat.

The village is in an ideal location for exploring both Loch Lomond and The Trossachs National Park.

Sunset in the Trossachs National Park

Aberfoyle to Callander

Leaving Aberfoyle, the route begins to make its way towards Callander.

These paths are quite similar in terrain to the ones leading from Drymen to Aberfoyle, with the addition of a few bogs.

A gentle rise through the forests allow for spectacular views over Lochs and the town of Callandar.

This town is considered to be one of the last stopping town on the way to the Highlands of Scotland due to the Highland Boundary Fault.

Once in Callandar, you truly are in Rob Roy Country.

A View of the Town of Callandar

Callander to Strathyre

The road from Callander to Strathyre is quite gentle as it mainly follows some trails through a forest and a well-maintained bicycle track.

Strathyre is an old village which was first built on a popular cattle-droving route – one which Rob Roy used.

When the railway was introduced in the late 19th Century, the village was expanded to accommodate more traffic.

The village is surrounded by forest which makes it ideal for really exploring Rob Roy’s stomping ground.


Back to Old MacGregor

Rob Roy continued into the line of work that he was raised in to – cattle-droving.

He would transport cattle up and down Scotland, a route that is now known as the Rob Roy Way.

Interspersed with this legitimate business venture, Rob Roy also provided another service to the cattle farmers of his area.

In a ‘protection racket’ style business, Rob Roy would provide protection to local farmers from cattle thieves.

If the farmers opted not to avail of this service, their cattle would mysteriously go missing…

Rob had control over the cattle thieves in his area, meaning he could absolutely guarantee protection – or the opposite.

A Highland Cow

He gradually did build up a reputation as a trusted businessman however, and in 1712, he obtained a loan from the Duke of Montrose in order to increase his own stock of cattle.

Unfortunately his chief cattle herder disappeared with the large sum of cash, leading to Rob Roy defaulting on his loan from the Duke.

This enraged the Duke, and he declared Rob an outlaw.

Mid Stages of the Route

Strathyre to Lochearnhead

Leaving Strathyre, you will walk through forests and along more cycle paths. On this section of the route, there is a short but somewhat steep climb.

A view over Loch Earn

Lochearnhead to Killin

Lochearnhead sits on Loch Earn, a quiet lake whose perimeter is overshadowed by hills and mountains.

A cycle path then follows on to an old railway track. This gives way to to more forest tracks, leading to a last descent towards Killin.

On the approach to Killin, you can see the Falls of Dochart which run through the village.

Killin to Ardeonaig

A small road leads out of Killin, incorporating a long and large climb.

A high trail across the mountain leads along the shores of Loch Tay.

The terrain here consists mainly of boggy land.

A view of Loch Tay

Rob Roy’s Later Life

Rob attempted to exact revenge upon the Duke in the following years.

He continually raided and stole from properties belonging to the Duke, earning his ‘folk hero’ status.

It was because of his ‘steal from the rich’ style that he became known by some as the Robin Hood of Scotland.

Rob was eventually caught and imprisoned.

Blac and White Photo of Rob Roy MacGregor

A book was written about Rob’s exploits while he was still in prison.

This lead to him being viewed as a ‘lovable rogue’ and his eventual pardon.

Rob Roy MacGregor was released from prison in 1727 and moved to Balquhidder, where he lived peacefully until his death in 1734.

End of the Hiking Route

Ardeonaig to Acharn

This part of the route takes in the beautiful Scottish countryside, remaining on the southern shores of Loch Tay.

A minor road leads out of Ardeonaig and follows the route for some distance.

Acharn to Aberfeldy

You pass by the scenic Falls of Acharn while ascending along grass-covered trails.

There is a fine variation of terrain here: fields, forests and moorland.

The Falls of Acharn

Aberfeldy to Pitlochry

On the final leg of the journey, you follow the River Tay out of Aberfeldy.

You begin to climb over rugged mountain terrain before your eventual descent into the final town of Pitlochry.

For more information on walking the Rob Roy Way, just get in touch.