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Trip Highlights:

• Experience breathtaking views as you walk through the heart of Scotland’s rugged landscapes

• Discover charming villages and ancient forests along the iconic Rob Roy Way trail

• Embrace an unforgettable adventure filled with history, nature, and Scottish beauty

Walk in the footsteps of one of Scotland’s most brilliant outdoorsmen, legendary outlaw, and greatest heros – Rob Roy MacGregor. Through green meadows, along the coasts of sapphire lochs, and across the feet of snowcapped Munros (peaks over 3,000 feet), you walk as he did in the beautiful Scottish Highlands area of the Trossachs.

Scottish hiking is always memorable, regardless of where you travel. The Highlands, however, are a land of magic, the images of which will be etched in the minds of travelers forever. It is because of this that our trek is surely to be a more relaxing one than MacGregor’s.

The keystone of a clan known throughout the Trossachs and the rest of the Highlands for illicit cattle driving and dealing activities, MacGregor was a sort of Scottish Robin Hood. Stealing and conning wealthy farmers and land barons was his specialty. Bestowing his spoils among the empty hands of the less fortunate was his passion.

He and his brother, under the banner of the Lennox Watch, offered cattle protection services in exchange for payment. If payment was not made, the cattle would disappear. His racketeering continued successfully for many years until his main patron, the Duke of Montrose, turned against him. The rest of his life was spent traveling across the Way, ambushing and haranguing Montrose and his servants at every possible opportunity.

Despite many attempts on behalf of the Duke of Montrose to capture and execute him, Rob Roy lived for decades squatting in the homes of welcoming strangers, friends, and fellow clansmen, traveling through the Trossachs and hiding out in the thick, murky forests. When he eventually did pass away, he was already well into his sixties, and it was peacefully, of natural causes, and asleep in his bed! It is for this reason that on his gravestone the epigraph reads simply: “MacGregor despite Them”.

While walking the Way, you will not only be steeped in history, but also immersed in one of the most pristine natural environments of Great Britain, traveling through waterside, woodland, and moorland ecosystems. The trails are lined with ruins of every age: prehistoric stone circles, Roman bridges, and, of course, the remnants of the Jacobean era.

At day’s end, enjoy spectacular cuisine and exceptional accommodations in the finest B&Bs and hotels nestled in the pastoral villages along the way.

Learn more about the Scottish Highlands destination