Map of the area around Overlook

...the place seemed immeasurably huge. Mostly the towering walls had been constructed of a grey-white stone but in places blocks of different colors had been worked in, along with silver, copper and gold, to scrawl the whole with cabalistic patterns..

Murgen, She Is The Darkness

Overlook was Longshadow's fortress and was the southernmost building of significance in the Shadowlands. Even when incomplete after 20 years of work, the height of the fortress's towers put the Tower at Charm to shame. The exterior walls were 100 feet tall. They were covered in gold and silver runes and protective spells. At night its towers were shining like lighthouses, in order to keep the shadows away. Longshadow never completed his fortress.

At the start of the events of She Is The Darkness, Overlook and Shadowcatch (the city whose purpose deemed by Longshadow was to ensure his fortress' completion), were struck by a devastating earthquake, leaving Shadowcatch in ruins. Following the advice of the turncoat Mogaba, Longshadow would allow refugees from Shadowcatch to reside within Overlook's walls.

Following Longshadow's defeat at the Battle of Charandaprash, Overlook itself was besieged and seized by the Taglian legions serving the Black Company leaders Croaker and Lady.

After much of the leadership of the Company was imprisoned in magic stasis by Soulcatcher, Overlook was next occupied by Sleepy the Annalist, her key ally Ky Sahra, the wizards One-Eye and Goblin, and what remained of the Black Company. From the tower, the Company waged the losing Kiaulune wars against Soulcatcher's Protectorate. The fortress was eventually reduced to dust by Catcher, who spent two years analyzing the sorcery imbued in the structure's walls to create spells that would obliterate the stone within.