In -2368 DR, at the adamant insistence of the Terraseer, the Empire of Netheril began earnestly colonizing the Savage Frontier. They established several outposts at which Netherese travelers heading west could get fresh horses and supplies. The Terraseer himself identified a perfect spot for one such outpost to be built north of a mineral-rich mountain range not far east of northern Illefarn. However, the site was infested with owlbears, so the Terraseer had his scouts destroy the 3,000-strong population of beasts in an event known as the Caravan War. The outpost was named "Old Owl Well" after the victory over the owlbears.
Once secured, arcanists arrived and began to drill a hole that eventually dug more than 5 miles below the surface then, with an extensive system of pipes, they established an everlasting water supply that could provide 20 gallons per day. The enclave of Quesseer was built nearby, which served as a trading post for the Netherese and nearby demihuman nations until Quesseer's abandonment in -2095 DR.
Old Owl Well remained a strategically important watering hole. Every group that held any power in the nearby regions since the Netherese left (except the Harpers) claimed ownership of the site. Since 1360 DR, a tribe of orcs held Old Owl Well for at least a decade.
The Neverwinter Greycloaks under the command of Callum of the Neverwinter Nine retook Old Owl Well from the orcs so that a direct trade route to Triboar and Yartar could be re-established in order to bring more money into the coffers of struggling Neverwinter, still recovering from its war with Luskan. Thankfully, the efforts of the Kalach-Cha and the paladin Casavir allowed Neverwinter to keep possession of the site for the foreseeable future.
In approximately 1480 DR, Old Owl Well was nothing but a ruined watchtower that had nothing but a few crumbling walls. However, the well still pumped clean, fresh water. During that time, a Red Wizard of Thay named Hamun Kost, who had tattooed himself with necrotic symbols, began searching the area for hidden lore of an ancient time.
In the time of Netheril, Old Owl Well was occupied by a group of warriors who kept the peace and a smaller group of arcanists who used crystal balls to scry on nearby Illefarn, watching for signs of aggression.
Nearly 3 millennia later, the orc occupants of the Well numbered around 600. Unlike previous owners, the orcs did not charge travelers to use the well; instead, they simply attacked passers-by. Adventurers or particularly capable caravaneers occasionally left them beaten, but they never did enough lasting damage to threaten the orcs' survival.