I recommend you do this Letterbox walk and Cronk’s walk in one hit – one out from, and the other back to, the Red Lion where both walks start – as both walks come together at the North East Cottage. Rupert’s path runs higher up Green Mountain than Cronk’s. It doesn’t really matter which one you start with – I started with Rupert’s so this review and my separate review for Cronk’s walk are written assuming you do likewise. The walk out and back will take around two hours.
The actual path starts at the north-east corner of Garden Cottage (available for rent via the Obsidian Hotel though I don’t recommend it. You access Garden Cottage via an arched gate at the Red Lion where you should park your vehicle. A rough area map is included in my general Green Mountain tip.
Cross the stile behind Garden Cottage and continue till you reach a fork in the path – stay on the upper path for Rupert’s ( the lower path is Cronk’s walk).
Rupert’s is probably the oldest path on Green Mountain, built to link the gardens and Garden Cottage with North East Cottage which was built in 1834 by Captain William Bate for this own use.
Much of the walk was bordered by a metal railing fence of which only remnants remain. While the walk is relatively easy going you do need to exercise some care as the path is narrow in parts and runs along the edge of a cliff. The addition of vegetation over the years along a lot of the walk means that a potentially fatal fall can now be halted and in fact you will need to, for the most part, peer hard through this vegetation to realise you are walking on the side of a cliff face. This wasn’t the case in 1872 when Private J Gallaway fell to his death – you will come across a memorial to him built into the black clinker cliff face.
Just before Gallaway’s memorial you will encounter a cave adorned with Maidenhair Fern (one of a number of small lookout caves you will see on the walk) built into the hillside. Unlike the other caves this one has a plastered ceiling (note the graffiti) and a seat built into the wall. This cave also contains the letterbox for this walk so do leave a message in the book and record your visit with the rubber stamp provided
Along this walk we came across numerous shy but inquiring wild sheep and a number of colourful land crabs (picture included in my Cronk’s walk review). We had stunning views towards to east coast of the island from this walk – pictured above.
Address: Green Mountain
Directions: Park at the Red Lion