These Hobbits (and their friends) only ascended and descended the external faces of buildings.
Illustrative illustration from the original Guide. Cover of a modern edition. Further reading by the same author.The whole climb is very similar to the Shirrif House Main Gate; the second pitch is harder and the first pitch easier than their counterparts.
From here, if the climber be making a circuit of the Great Houses, she can go down the north side by a similar pipe. If she would do this circuit, she must have a companion and a short length of rope. To get on to the Elf-tower, the Hobbit-ladder must be used: one climber supports the other on her shoulders. She then stretches her arms upwards, and keeps the upper Hobbit's feet from slipping as she goes up. The rope enables her to follow.
If the circuit of Great Houses is not being made, it is best to descend on the south side. The descent is also easy, and we are back at roof-level surprised at the simplicity of the climb. The ancient Fairbairn Guide sighs over this, but consoles itself as follows: "Old age creeps upon every pipe, and will upon this one in its turn. Then climbers will be forced to use illegal methods --- Elanor forbid the throwing of stones, but perhaps the throwing of balls of string from side to side --- in order to make their peak; or else give up the Great Houses circuit and sigh for the good days of old." Old age is a long time creeping; the pipe is still as good as new.
In drawing sketches for the Great Undertowers Gate, we had an exciting half-hour. It was half-past seven in the evening, and several people were walking about in the Great Library Court. This meant that the easel was bound to be seen, but the party had a better chance of mingling with the common throng of visitors if any Shirrif should see them. In the dead of night Hobbits on nefarious business feel very conspicuous; in the evening, if they are sufficiently hard-boiled, they can talk and joke with their pursuers, unknown and unsuspected (Burglars, please note.) It is the unexpected that has the best chance of success.