Cobblestone is a large-sized map, and had quite significant vertical combat in its earlier iterations. In earlier versions, it is fairly easy to take fall damage due to the high height of many of the map's drops. Bots in early versions of the game will also occasionally fall to their deaths. Additionally, this map is open, making snipers very useful.
Bombsite A is located right next to the Counter-Terrorist spawn, and bombsite B is located around a large statue. Terrorists spawn in lower area with a sniper tower nearby, a tunnel to bombsite A and stairs to bombsite B. Path to bombsite A leads to a very open area leading either to A long, underpass or to bombsite B via a connector. Path to B leads to tunnels with B long and a drop.
Wingman version of the map has only bombsite B, with Terrorists spawning in tunnels and Counter-Terrorists spawning in the connector between A and B bombsites.
The map was designed by David Johnston after completing Dust. He had a large castle for a map in mind, and created cs_cstle (Castle). Chris Ashton supplied Johnston with the necessary textures. However, the map was rejected due to gameplay issues. Johnston decided to restart the development and quickly made a new castle-themed map, which became de_cbble (Cobble), and was designed around similar principles as Dust.
It was first introduced in BETA 6.5, and saw a few more revisions before its final release to make it more competitively viable.
Cobblestone was re-introduced as part of the December 18, 2013 update. Valve performed a major overhaul to the map, graphically and strategically. Nearly all of the crates were removed and replaced with more realistic props. The hallways had become filled with museum artifacts instead of crates, similar to Piranesi. Additionally, the map is littered with some construction equipment and Medieval props, completing the transition from just an old medieval castle in the previous games to a historical museum and tourist attraction somewhere in France.
The map was significantly updated over many updates. Some sniper positions were removed, while new connectors were added.
According to the official description of de_chateau, the Terrorists were able to successfully bomb Lord William's country farmhouse (Cobble). However, Lord William survived, and was rebuilding his summer investment (Chateau).
In Guardian mode, the map's only hostage is named "Lord William."
A sign near the door handle on the toilets changes color when a person is occupying the toilet.
The pre-rendered shadows on the map were mismatched in directions to the live-rendered shadows on the map.
A symbol is hidden in a box near T main entrance to Bombsite B, visible by noclipping into it.
In the Cobblestone collection, the CZ75-Auto | Chalice is a reference to the Chalice in the movie Indiana Jones: The Last Crusade, as its flavor text is "Choose wisely".