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Hilltop was located in the Silver Marches. The trail to Hilltop branched off the trail between Everlund and Sundabar, between Lhuvenhead and Jalanthar, which were the nearest communities. To the east of Hilltop was the village of Blumberg and far to the west, down the River Rauvin was Everlund. It was described as a very inhospitable land due to its cold climate and potential hazards, such as roaming monsters around the area.
The area was governed by the elected mayor, Veraunt Shuttlescomb, for a time. Although falling within the boundary of Luruar, it was not one of the signatories of the League of the Silver Marches, being too small.
The towns were at one point found upon by ex-soldiers from the Zhentarim armies who were distrusted by neighboring towns due to their knowledge of Zhent's history and behaviour. Similarly, adventurers were also drawn to the location potentially due to the possibility of roaming monsters and hazards that awaited them.
In a particularly cold Kythorn of 1372 DR, Hilltop was attacked by a large group of kobolds. Casualties were relatively light, with only a few militiamen and two civilians killed in exchange for dozens of kobold dead. Drogan Droganson though, the one who could likely do the most to repair the damage to the village was poisoned in the attack and incapacitated, leaving his eldest apprentice to try and solve everyone's problems. This apprentice would go on to do great things like destroying the Netherese flying city of Undrentide and defeating the Valsharess and Mephistopheles.
Hilltop won second place in the "Communities in Bloom" competition, losing to Blumberg (it is unknown if there were any other entrants), which was sacked by Gnolls on the same day as the Hilltop kobold attack.
The main point of interest was Drogan Droganson's adventuring school.