[From my 2nd ed. AD&D Blackmoor campaign, currently on hold. The version of Blackmoor I was using is a combination of Dave Arneson's Blackmoor and Gary Gygax's Blackmoor. Likewise, the Keep on the Borderlands I was running was a combination of the original 1980 module, Return to Keep on the Borderlands, and Hackmaster's Little Keep on the Borderlands. The following is largely a reworking of material from Little Keep.]
The eastern-most, and largest of Gloomen County’s three North Keeps is Kendor’s Keep. Kendor’s Keep is located in the forested Westwood Hills, roughly equidistant from Lake Gloomey and Vestfold, both 50 miles away. It is five miles west of the Sherpty Channel and two miles northeast of the Village of Sittingham. The remote Hamlet of Herntable is nine miles to the northwest of the Keep. Both Kendor’s Keep and the Village of Sittingham are located in the Westwood’s Throat, a strip of land free of forestation that runs southwest from near the edge of Sherpty Channel and opens to the fields surrounding the Village of Chattingham (almost halfway to the Town of Lake Gloomy).
For 200 years, the Archduchy of Blackmoor and the Barony of Coot have been at odds. Coot has invaded twice, both times striking primarily at the Earldom of Vestfold. The County of Gloomen has been spared the brunt of both assaults, but its counts have always been conscious of the mere 10-mile wide channel separating Gloomen and Coot. Mainly out of fear of Coot, the north part of the county is largely deserted, save for a few hamlets and the three North Keeps.
The easternmost keep was built after the first Coot Invasion and was built to be the largest, for fear that the Sherpty Channel and the old road leading from it to Lake Gloomey (now gone and replaced by paths; only the Westwood’s Throat remains to show where the road once was) could be used as an invasion route by the Cootons. Kendor was the first castellan who oversaw (and, it is said, even helped plan) the final stages of construction of the keep 100 years ago. The stone for the keep was quarried from Sittingham, Chattingham (its stone quarry was played out 50 years ago, though), and even Prestone. Kendor’s Keep has always enjoyed a symbiotic relationship with the Village of Sittingham, receiving most of its foodstuffs from there (and most of its finished goods from Lake Gloomy or Harblebury). Sittingham is also where most of the conscripted soldiers have to go to unwind when off-duty, so Sittingham has a whole section of the village set aside for their kinds of needs.
Kendor’s Keep sat uncontested for its first 25 years. At that point, the village of Sage’s Tower was fortified and a concerted effort was made to drive monsters from its peninsula. Swamp orcs fled to the southwest into the Westwood and -- although too weak in numbers to attack Kendor’s Keep – they essentially laid siege to it for three years. In that third year they were assisted by goblins and gnoles dispatched from the Egg of Coot and nearly overwhelmed the keep’s walls, but were wiped out in their fruitless assaults. This occurred simultaneously with the First Coot Invasion in modern times and was seen as a testing of Vestfold’s neighbors, if not an outright effort to outflank Vestfold. The men-at-arms at Kendor’s Keep were told to remain vigilant, but instead celebrated and two generations of their successors grew increasingly complacent.
That complacency was broken 38 years later – 35 years ago – with the Second Coot Invasion. This time, while the Coots again focused on the Glendower-Blackmoor area of Vestfold, a sizable force of 3,000 goblins, gnoles, and orcs sailed down the Sherpty – just as the counts had always feared – and assaulted Kendor’s Keep. The monstrous forces overwhelmed the walls and slugged it out with the defenders in the streets of the Middle Bailey. Half of the men, women, and children in the keep died that day, but the keep held. Luckily, allies had rallied around Blackmoor in anticipation of this invasion. Rovers of the Barrens rode to the keep’s rescue in numbers said to be 1,500. The keep’s invaders were routed.