Let's do what I did for the Timischburg map. I'd like to actually develop some of these line items with more detail, but for now, these simple summaries will get me up and running. You'll have to actually enlarge the map in order to use and read it, but that's OK. Open up a new tab, slide it to a second monitor, or just go back and forth, or whatever.
Anyway, the point of this is to give a quick summary of the locations, without much in the way of any detail. However, it's sufficient to start planning stuff; I used these exact same summaries in my Timischburg map to adopt the Carrion Crown adventure path into my Cult of Undeath project. It works just fine for high level planning, but obviously more detail will need to be added at the micro level to make it really usable. That's OK, if someone is using this without me, they can obviously add such detail or steal it as necessary, and if I'm going to use it, I'll get around to doing so as well before I do. But it's easier to build off of a framework that's already in place than without one.
Anyway, starting in the top left corner and spiraling onwards counter clockwise. I'm not talking about every single item on the map as its own entry; but I've italicized in the text towns or features that I'm discussing as part of a larger feature.
The Wolfwood: This large forest is famous as home to loads of wolves, woses and wild barbarians and Wendaks. In reality, it's mostly just very large, tangled and untrammeled. Logging is done on the southern edges and some isolated woodsmen and hunters venture a bit deeper into the woods, but they're more likely to not come back because they got lost and had an incident with natural causes then an attack. Although... those do sometimes happen too. The bandits of The Hood's Cartel lurk under the eaves of the Wolfwood as well.
Hillmen mostly venture only on the south and eastern edges, in places like Pineytop, where great logs are cut into smaller pieces of lumber. Nobody really knows what lies deep in the woods, especially where it borders the sinister Plateau of Leng, but it makes a forbidding boreal barrier across the entire northern edge of the Darkling Sea.
The Darkling Sea: This very large freshwater lake, roughly equivalent to one of the now greatly shrunken pluvial lakes of the past; Lake Bonneville, Lake Lahontan or Lake Manly as examples. There are a few port towns on it's shores: Cayminster, an independent hillmen city state unaligned with either of the two major powers in the region, the wild frontier town of Sour Creek, the tiny Upwater aligned site of Ipsbottle Ferry, the nearby rival sponsored by the Grand Duke of Waychester in the form of Milcastle, and the end of the river city of Omsbury.
The Darkling Sea itself is notorious for cold dark waters, frequent stiff winds and rough seas, and frequent fogs, although fierce storms are rare. The large Cherskii Island is unsettled although disquieting rumors told by sailors who have stopped there briefly suggest that pirates, cultists, or worse may yet linger from even as far back as the time that the kemlings built black fortresses on its cliffs that now stand as bleak ruins frowning on the lake shores.
The Rudmont Escarpment: A huge fault line from ancient times created this massive cliff face that runs for hundreds of miles north to south at the western edge of the Hill Country. Sometimes the slope is (relatively) gentle, although always steep, but for most of its length, it is a looming wall of tumbled and broken rock faces and buttresses between 1,000 and 2,000 feet tall Crossing the Escarpment to end up on the much higher Plateau of Leng side (or vice versa; down to the Boneyard) is impossible at most points, but there are a couple of passes that allow travel. Around the northern edge is one such location, and there is an old jann settlement of Vuukrat still located there. Much further south is an additional jann settlement at Sinjagat, and the eponymous Sinjagat Pass. At the southern edge of the escarpment, where it dives into the Indash Salt Sea is the wealthy kemling city-state of Simashki (often called Glittering Simashki.)
Little is known (by the Hillmen, at least) of what is on the Plateau of Leng above the Escarpment, other than that the nations of the kemlings and jann are up that way somewhere, and they in turn whisper darkly of the Mind-Wizards of Leng and their hidden city. No hint of the Mind-Wizards have ever come down from Leng as far as anyone knows, however.
The Boneyard: This desert basin is sandwiched between the Darkling Sea and the Rudmont Escarpment. It is so named because of the large number of skeletons, mostly of horses, kemlings, jann, and Drylanders who have died in ancient conflicts across the region and were left to bleach in the sun, since nobody was there to bury or burn the bodies following the withdrawal of the great empires of the past from the territory. Old battlefields are not exactly common, but turn up from time to time, with half-buried bones, rusted old swords and more littering the ground, poking out of the dry dirt or half covered by dry grasses or other low, scrubby bushes or cacti. Drylanders still wander the desert, and can make life difficult for those attempting to travel the Boneyard, but they (mostly) respect the sanctuary of the few roads that cross the territory, between Sinjagat and Cayminster and Sour Creek, etc.
The territory is a desert basin, but the terrain is not flat or low relief; large cliffs, spires, ridges and even entire sky island small mountain ranges are prevalent across the territory. Often if these are high enough, these sky islands can be covered in thicker tree covering; juniper, mesquite and pinyon pine. Wildlife is also common across the territory; wild boar, javelinas, pronghorns, deer, cougars, coyotes, lions, hyenas, terror birds and more; similar to those that live in the Golden Wold to the east, although not quite as prevalent because of the drier terrain.
The Chokewater River may slow to a trickle on dry years, but it does make it almost all the way to the Escarpment before it finally gives up and ends in a marshy land of willows and cottonwoods, where the small hillmen town of Rackgrove is located. The primary industry here is mining, smelting and cattle ranching, and hillmen go out into the territory of the Escarpment to find iron, silver and gold. The smaller town of Quarry Hill just to the south is a staging area for iron ore in particular to make its way to Rackgrove to be smelted. Rackgrove is a settlement originally come from Upwater, and most of its business is still with them, although the political machinations of the the leaders of the two large city-states are of less concern this far into the frontier, and Upwater hillmen are perfectly happy dealing with Waychester hillmen as long as the Lord Mayor's troops aren't watching.
The Golden Wold: This high plains environment is not strictly just open prairie, but more like a live oak savanna where open grasslands are dotted frequently by stands and groves of trees. Thriving with animal life: feral longhorns, buffalo, pronghorn, deer, etc. make it a rich environment for predators as well as hunters from the hillmen. The Chokewater River runs through the center of this area, and the river is navigable, broad and difficult to cross. Major bridges exist only at Upwater and Getfield, and the river is too broad and deep to have fords until after it's split further downstream. These two cities are built mostly on trade, and serve as major regional hubs for homesteaders, farmers and more throughout the area. Upwater is ruled by an elected Lord Mayor and serves as the most important city-state in the entire southern Hill Country area, with most of the rest of the southern cities, towns, villages and hamlets owing at least some degree of fealty to it, for which in return Upwater recruits troops and officials who provide a measure of protection from bandits, Drylanders, criminals and more.
To the southern end of this region are the Copper Hills which, as the name implies, are a source of copper (and tin) and Cockrill's Hill is a fairly significant settlement located here where the hillmen work the hills for ore. As the hillmen first entered the area, they found scattered small settlements and farms of orcs and goblins, finally finding a hub of sorts in their community of Sharkul on the far side of Lake Byewick. While the hillmen usually look warily at orcs and goblins both, they do value their ability to serve as fairly cheap and strong labor, and many have become integrated as an underclass at Cockrill's Hill working in a variety of manual labor jobs.
The Sabertooth Range: This mountain range is on the far side of the area to be detailed, and they are eroded yet sharp and very tall sierras made of pale gray granite—they can be seen as looking very similar to the Sierra Nevadas, the Wind Rivers or the Beartooth Mountains; covered in pines and conifers, and the source of the Chokewater River. The small town of Pickdown is located here, which provides some relief from needing lumber from the northern rival. The Haunted Forest also surrounds this range (as well as its further northward slate and shale counterparts, the Knifetop Mountains) but that has already been detailed.
The Kvuustu Steppe: With a name lingering from the time that the jann empire that once ruled this area, this vast prairie is today lightly settled by lingering hamlets of jann, kemlings, and an increasing number of hillmen. The Hillmen themselves usually render the place as Kavoostoo or Kavustu Prairie rather than utilizing the (to them) uncouth combination of consonants and vowels of the jann. Threats from the northeast, especially thurses, can be found here, and occasionally even Drylanders will pass through this territory. In the far north, a recently founded town of Cursed (Daikos Colony) has popped up, continuing to flee from the savage Inutos. Although most of them still remain in their embattled home of Lomar, they have begun to flee even further south; this being one of their new vanguards and first major push into the Hill Country region—another major settlement area is in Timischburg on the coast. The Chatterwash River flows from the Knifetop Mountains across this region and is navigable from many miles upstream from its fork at Waychester all the way to the Darkling Sea on both forks.
In the center of the region, the terrain rises in a series of limestone karst hills, the Waychester Karsts, and this is the regional capital of Waychester is located. Ruled by a Grand Duke, it is somewhat more traditional in its form of government than its southern rival Upwater, but the court of the Grand Duke is unfortunately riven in dissension, and the Grand Duke has imprisoned his own wife in a tower for treason. It's unclear why she hasn't been sentenced and executed, but this dissension has brought the northern region to the brink of civil war. Which, as the southerners say, at least keeps them from turning imperialistic ambitions on their territory. The southerners are only ruled by an elected Lord Mayor and have no interest in any kind of hereditary ruler, while the Grand Duke looks to unite the entire region and declare himself a true king like his would be peers of nations like Normaund, Culmerland, Trondmark, etc further to the north.
The Waychester Karsts are also a good source of coal, and much of the coal from the entire region comes from here, and ships far to other nations in the north and east in particular.
The Knifetop Mountains: A mountain range of formerly glacially carved slate and shale. It is also surrounded by the Haunted Forest, and the small region of Eltdown is located here as well. Eltdown has only tenuous connections to the Hill Country, although some hillmen do live there, or trade there, it is primarily a Tarushan village. (Although Timischburg does not claim it either, or make any attempt to manage the area.) Eltdown and the surrounding fens and lake are already detailed here.
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