Revised map

I added a scale and index of town names. I think Fireball Gulch is in the right general area. I labeled the two that didn't have names as Gresham and Elfsheim. I think an Elven port in that area makes sense. I've thought about scattered wood elves living in these hills and forests, and it makes sense they'd have gathered together in a port town.
I once started a backstory about Elves from this area going on the warpath through the mountains to the north in order to attack Dassal downriver from the hills. This group got lost somewhere unknown, and their homeland scattered in the power vacuum. With the advent of trade routes and sea travel, it makes sense the elves would materialize in their own small harbor near the hills and forests of their heritage.

Greater Bayport & Twin Forks

This is a rocky and treacherous land, rising steadily and directly out of the deep ocean to towering mountains full of cliffs, heavily wooded ravines, and extremely difficult travel. Still, the shoreline around most of Barmet Bay is of a much gentler nature, with broad expanses of open pasture and rolling hills nestled snugly between the deep waters of the sheltered bay and the ring of cliffs looming over the entire area. The southern shores of the bay feature rolling moors stretching south for miles, but abruptly dropping within meters of the water’s edge to a shelf just above the tides. This shelf houses regularly dispersed fishing villages along the bay, with alternating beaches and rocky shores along the jointure of land and sea. In the stretches between them are cliffs riddled with caves.

To the east, the Willow River winds through the long valley stretching east, narrowing as it rises away from the sea and disappears into the forests and hills southward. The rolling farmland around the city of Bayport, located near the mouth of the Willow River, is fairly heavily settled, and features regular trade within the city itself. There are regular trade routes upriver, overland across the moors to the south, and out of the port itself across the open sea. Local transports connect the southern fishing villages with the city, and larger ships commute passengers and goods out of the bay, across the sea to Sidney and Lenay to the west.

Most of the trade with Bayport comes from across the bay with Lenay, and with the greater southern kingdom through the ports of Mussel Harbor at the southern edge of the great sound. Bayport rose to significance by connecting the lucrative overland routes out of Waynesburg, Farmington, and Dassal safely with the ports of Oceanside and the Kingdom. There is also a brisk trade with the fjords of Northern Wingmar, located over the towering mountains north and west of the city. While the distance over the mountains is not great, the terrain is extremely severe and constantly endangered by beasts of the wild, making the longer sea journey around the mountainous peninsula preferable and more profitable. Unfortunately, the mountains are home to many fringe outlets of society that relish the wastelands and unmanaged paths. Also, the waterways are vulnerable to piracy crossing barren waters bounded by open sea and immense, uncharted cliffs.

Two day’s journey northeast of Bayport, along the High Road that leads up into the mountains towering over the valley and bay, lies a long valley following the East Branch of the Willow River. Leaving the valley, the road winds upland through scattered copses of trees, along and through several ridges and valleys that divide the seemingly flat area of the lower hills. Following the east branch of the river, the road runs to the village of Twin Forks, nestled in a small valley. Rising over the village of Twin Forks to the northeast, the Monastery of Kord commands a view of the surrounding valley from high on Monk Hill, and overlooks the Mill Lake and Hammer Falls.

Twin Forks is a small village, named after the two branches of water that join at its shores to become the main river. One bright, young stream rushes down out of the western hills, which steeply rise into the mountains. A rough track follows it up into the desolate peaks, leading miners and adventurers alike into the dangerous and wild reaches of the high mountains. The other branch is the Hammer Stream, and stems from the Mill Lake further up the valley, crashing down the Hammer Falls before slowing and broadening above the fork.

The village is small, tough, and sparse. There is one inn, one general store, and one trading post. The store caters more to the mining crowd, offering foodstuffs for all, and basic adventuring kit along with the usual mining gear of shovels, picks and rope. The trading post attracts more hunters and river men than miners, and features hides, ammunition and simple weapons. The inn is a catch-all melting pot, always on a slow boil.

Mining and trade keep this town alive. Their traffic and business are essential for bringing people and gold together within it. Anything threatening the safety of travel and activity around the town jeopardizes the safety of the city itself. Since Bayport is the primary downriver connection with the rest of the area, the livelihood of much more than Twin Forks relies on safe passage through the valley.

Lately there has been an increase in nefarious activity throughout the valley surrounding the town. Ambushes have occurred between Twin Forks and Bayport, as well as on the other feeder roads leading into town. Take your pick on the identity of the bandits… some claim river pirates, some claim orcs, others insist they are dark elves, failed adventurers, etc. Who knows? Maybe they’re all right?

Trouble has come to the valley. There is unrest everywhere, and it is spreading quickly. The trails are threatened, the mill pond is threatened, the monks are shutting out the world, and dark things move in the night.

Townsfolk - talkative, but not much information.

“Sure its rough out here. Always death and crime. Always some new hotheads rushing through to clean things up… just like you. Always new ones coming in soon.”

They offer a few nuggets though, mostly common sense.

“Stick to the road… don’t wander around the warehouse after dark… purify the water before you drink it… be careful around the monastery, weird doings out there.”

Adventurers - mining look. There is a certain naiveté about them. New to the life, in all likelihood. They want danger & excitement. Much talk of roads and mines and hitting it rich. 

“It’s odd though… the raids seem to be centered around the monk’s mountain. You’d think it would be more in the hills, around the mines. There’s nothing exciting about a bunch of monks, right?”

Magic - two dark elves, sticking to the shadows, very secretive. Likely they will learn more about you from you than vice versa. They are dismissive of most topics, but will pay careful attention to any talk of magic or the monastery.

There are three things situated north of Twin Forks, the Monastery of Kord, the Dwarven mills at Hammer Falls on Mill Lake, and a whole lot of unexplored wilderness! As a result of this, the road is not heavily travelled as a rule, but because of its importance remains in good repair. It is wide and firm, enough for two carts to pass along most of its way, but one can travel for miles without encountering anyone. At least, they hope to be able to…

After five miles out of Twin Forks, the road leading to the Monastery of Kord splits off to the right, crossing a pleasant meadow, filled with wildflowers, before rising gently up the side of the lone hill where the monastery sits. Once it starts to slope upward, the road disappears into the heavily wooded sides of Monk Hill. Unlike the main road to Hammer Falls, this is barely more than a trail. The road itself is heavily overgrown, and narrows significantly as it crosses to the trees. The monks maintain a solitary life, seldom venturing far from their own walls, and only rarely coming off their mountain to interact with the greater world. Much of what they need they produce, and the rest can be traded for weekly with passing supply wagons. Even so, they are known to be vigilant in defense of their isolation, and will not allow access unchallenged. They are averse to fighting, but will ask intent of any visitors, and defend against assault or particularly egregious actions.

The fifteen miles from this branch into Hammer Falls is a dangerous road, with many bandit attacks along the way. Mostly, these are goblin and orc raiders, but occasionally they will be the result of highway robbers who move back and forth throughout the countryside preying on exposed travelers. Consequently, wagons running from Twin Forks into Hammer Falls and the return travel in groups as much as possible. Otherwise, they recruit any willing sword-arms to ride along as protection. If this were a busier route, officials from the greater Bayport militia would be sent out to locate the goblin hideouts and rout them all, but as important as the trade route is to Hammer Falls, it is low on the priority list of the greater region. There are far more concerns in the city about pirates and river smugglers than inland bandits. On land, they are more interested in keeping the roads open from Bayport to Waynesburg and the traffic on the Great River.

The Monastery of Kord sits atop a slight peak rising above the surrounding ridge. It is nestled among the natural pine trees crowning the hill, concealed from obvious notice from the High Road running around the base of Monk Hill. There is a small, but clearly used, path leading away from the road, criss-crossing the exposed stone face of the hillside for several hundred feet before its slope levels. At that point, the path swings back across the hill in a broad gentle track, disappearing into some oak trees and scrub brush set back from the edge of the cliff. Access to the monastery is allowed during daylight hours with a donation to the gate wardens. These wardens remain hidden in the cover of the brush, with one sentry placed at the top of the switch-backs.

The monastery inhabits an abandoned castle situated atop the mountain peak rising above the town of Twin Forks. The original builder of the castle is lost knowledge. It has a dark and foreboding exterior that speaks to a possibly sinister demise. There are rumors of its destruction in some cataclysmic act, and hints that a dangerous magical power once was held within its walls.

“Consarn it! There’s supposed to be gold in them there hills… so why can’t we find it?”

The road out of Twin Forks is a fairly narrow, rough track, but it is heavily travelled, and well worn. The weather has been very wet of late, and the road is deeply muddied. The underbrush is heavy, and branches overhang the road. 

The road east is a wild and dangerous trail. It passes through a narrow and steep valley, overlooked on the north by the Monastery of Kord, before winding up into the mountain passes. The road leads up and over the mountains, eventually running into the Golden Lake on its western shore, where it intersects with the roads running north to Fireball Gulch and south to Dassal. The passes are known as the Mage’s Vale.

Bayport revision

I reshaped the bay north of Bayport a little for a better coastline. I think it makes it more like Barmet Bay in the books as well, with a sheltered bay a few miles across before the open sea. It's a more natural looking shape as well.

Maps - Northlands

Here is a map. This is everything in the north - Oceanside in the southwest, Lenay above it, then the bay where Bayport is - and Waynesburg and such on the river on the right hand side. Oceanside and Lenay are pretty well detailed - Waynesburg, Farmington etc. are sketchy here, but I have plenty of detail (especially Waynesburg) elsewhere. The gulf east of Lenay is pure sketch, though. I drew in the coastline, but just to have something; Bayport is marked as the red dot at the end of the horseshoe bay - but again, that's more a placeholder than anything.

The colors are meaningful - black is coast; I think I did rivers in blue; the browns are elevation markers - light brown hills, dark brown mountains; pink are political borders; green are major roads. Red dots are cities. Scale is roughly - 400 miles from Bayport to Waynesburg (the red dot by the lake on the eastern river) and from Bayport to Sidney (the dot straight west of Bayport, behind the little neck on the coast. Waynesburg's location relative to Lenay seems about right - but where Bayport should be between them, how big that water should be, etc., has always been something I've left to figure out. Everything between Lenay and Waynesburg is something of a blank.



Looking at this - I think Bayport should be closer to Lenay, probably - that extra bay looks a bit too big. I think I forgot the scale I was using when I drew it; I think I was using 20 mile blocks and thought I was using 10. But that's as may be.

Lenay

Lenay is a kingdom, located on a big peninsular, west of Bayport, a couple hundred miles away by water. It's a good sized country, divided roughly into two geographical regions. The northern 2/3 or so are highlands - the southern third called lowlands, though it is more mixed, with coastal plains separated by hills and moors in the middle. The north though is really highland: a very high mountain range runs through the middle of the country, dividing the highlands from the lowlands. Around these high mountains are foothills running to the sea on all sides. The far north, almost an island, is a wild place, its people fiercely independent, clan based, fond of their greatswords, pipes and haggis. South of this is the main bulk of the country, dominated by the mountains, though with good land and forests by the sea, especially on the west coast (where the rain and snow tends to fall.) Both east and west of the mountains, there are peninsulas, hilly places, wooded, cut up by rivers and little lakes, and so on. The coasts all around support decent farmland, and a rich maritime life. The only major city north of the mountains is Lenay City, the capital, located at the end of Lenay Sound, a long, deep bay separating the western peninsular from the mainland. It is a major port - a center of shipping to the far south (the Kingdom and beyond), to Oceanside, to Storm Island, and so on. In the last decade, or so, Bayport has begun to rival it, thanks to the increased trade from Waynesburg. There are no other major cities north of the mountains - there are plenty of towns and estates, especially along the coasts, but no areas that have developed into a real city.

The lowlands lay south of the mountains. (The Lenay Mountains, as they are called.) This area is lower, and in many places, a good deal less dramatic than the north. The west coast in particular is a pleasant land, a coastal plain giving way to rolling hills, that extends 30-50 miles inland, before rising into higher hills. (That are well short of being called mountains.) The west here is also wetter and more fertile than the east - it is good farmland along the water, and well into the hills, which also tend to be fairly heavily wooded on the west side. The east coast is a bit less inviting. Drier, the land less fertile - it tends to be moorland and heather on the east. The highlands run in long flat ridges almost to the sea, separated by low valleys, marshes and fens, as well as grassy and mossy plains. On both coasts (and in the interior) the land falls away to real lowlands in the south and east - much of the borderland of the country is plain swamp. There are 3 large cities in the lowlands. Newport is on the west coast, across Wickham's Bay from Oceanside. It is a port city - second to Lenay City (at least before the Bayport trade exploded), with strong ties to Oceanside and parts south. On the east coast is Sidney - another port city (located inside another big inlet, Sidney Gut, with Sidney Neck on the seaward side) - that has grown in importance with the increase in Bayport traffic. Finally, in the far south, is the city of Cinevia - it lies in the marshy lowlands where the inland countries like Regar and Troy meet Lenay and Oceanside. It is something of an anomaly in the land - the most recently conquered part of the country, and sometimes rather hard to fit in.

That is Lenay. Politically it is a kingdom, and has been for 150 odd years. Before that it owed fealty to the King in Norwich, due to some long ago conquest by the southerners - that had long ceased to be anything but a word by the time they put a king on their throne and declared themselves as good as anyone. Their location, on the sea, and protected by those mountains from land powers, has made them fairly impervious to outside trouble - but they tend to make up for it with domestic difficulties. They are in such a state now. There is a king - Nikolai II - who had the appearance of a fine king - a soldier, a hero, a would be conquerer - which got him in trouble. A couple years back he headed south to interfere in the affairs of some relatives - and got himself taken prisoner and held hostage. His brother Rudolfo is serving as his regent - and the story goes that Rudolfo has no intention of bringing his brother back any time soon. But he is meanwhile taxing the country to bankruptcy, in the name of paying the king's ransom. And this has brought about a terrible crisis. Rudolfo's men have been going around raising money; they have managed to alienate many of the barons (though others have joined in, hoping to use Rudolfo against their rivals), breaking up the country as they did; central authority has broken down - most power lies in the hands of factions, very little in the hands of the government. The main effect of this is that the navy - an almost completely national institution - has gone to seed: which has dire consequences on any efforts against piracy. (And of course, the result is that local authorities - merchant guilds and barons and the like - commission privateers to fight the pirates - though privateers are basically pirates with licenses.)

For all its troubles, Lenay is still fairly powerful and prosperous place. Though it is also a wild place - the highlands are often howling wilderness; the lowlands is fairly settled on the west coast, but the hills in the middle are still quite wild. The east coast is much less populated, and though perhaps not as likely to shelter dragons and giants as the mountains, there is plenty of cover for monsters and troublemakers of all kinds. The east is also plagued by piracy, all the way up the coast. This coast faces the waterways leading to Bayport, and, in the north, the high Oceanteeth mountains - it is a tempting place to hide. In the highlands, there are many deep, secret harbors, plenty of hiding places, and all of it not that far, by sea, from the barbarian coastlines of the Oceanteeth. The lowlands are a bit less inviting, especially for the big ships. The sea is shallower in this area, and tends to be very treacherous - there are only a few good, deep harbors, and even those tend to require pilots to get in and out. This area is also a bit out of the main shipping lanes, that run further north. Still - this is an almost open coastline for smugglers, and not that far from Bayport and the Waynesburg roads overland - there is a good deal of traffic back and forth, not much of it honest.

Piracy and Smuggling

Life on the water is a dangerous affair at the best of times, but the added test of protecting yourself and your goods from pirates and smugglers raises the danger level significantly.

There is an unspoken understanding amongst most of the river men and dockworkers that a certain percentage of goods and wares evaporates on any river passage. As long as the losses are minimal, they all look the other way. Occasionally, too much goes missing, or a particularly valuable or important bit of cargo disappears, and action is expected against the culprits. Generally, this is a tolerated interruption of activity, and quickly calms down to business as usual within a matter of weeks.

But how is it done? Such activity requires organization, far-reaching organization. This is the territory of the Thieves' Guild. They have chapters in most large towns, and tendrils in every town. They have developed a system where goods are siphoned off most transports and redistributed for their own gain. This is a sophisticated system that is highly structured centrally, but dispensed to loosely associated groups in every town or area. In this way, the system is protected when individual bodies get greedy or careless and overstep their mandate, drawing the attention of the law.

It is also a protection against an unraveling of the entire operation by the capture or exposure of any individual cell. As such, these river pirates tend to operate fairly openly, blending in with the normal citizenry of the town. They take care to conceal their nefarious activity, working late at night or early in the pre-dawn hours to avoid exposure. They generally tend to utilize fords and bridge landings to swap cargo between land and sea routes, and a rotating dock assignment to randomize the losses to traders in port. The goods are often stored in secret areas of abandoned or overstocked warehouses to avoid detection.

Open sea piracy tends to be carried out by organized gangs of well-trained and disciplined groups holding no ties to a greater organization. There are always those pirates powerful enough to command more than one ship, but even that is rare, as it requires too great a strain to maintain control over too many individuals. It is far easier to bind one ship and crew to their will than many, and likewise easier to manage dissent. These pirates tend to operate out of well guarded, heavily concealed harbors and cave locations on the many islands and coves around the bay. A popular area are the natural caves along the Shore Road leading east out of Bayport. These are popular because they allow the pirates to connect with networks of smugglers and bandits operating on land throughout the countryside. These groups work independently of each other, but in cooperation so as to properly fence stolen merchandise.

These groups are more direct in their thefts, as well as more apt to take everything they can get their hands on. They store goods in secret and fence them as wholesalers or any way they can. As a result, they tend to sit on greater stores of goods at any time.

Bayport

There are few things like a port town for variety. Bayport features a busy waterfront with a row of warehouses on shore mirroring a row of docks and wharves on the water. These handle many boats of trade coming from upriver and across the bay. The warehouses also deal with the many wagon trains running overland from town to town, connecting land routes with sea routes.
Centrally located, Bayport has become a hub for activity of all kind, drawing in traders from every compass point, by land or sea, as well as every race and class across the social strata. There are merchant stalls with a wide variety of goods from the entire surrounding countryside, as well as guild halls to cater to the needs and interests of the separate classes.
In addition to its healthy core of merchants and goods, the town has also become a gathering point and launch off for adventurers of all ilk. The easy access to any other part of the map is one drawing point, as are the promise of risk and reward offered by the forbidding mountains that tower over the low river valleys. Much gold has been found in those hills, as well as gems and other precious metals. And much of it has been retrieved at great cost, with vile monsters drawn equally to it, along with outlaws and bandits of all sorts.
The town is fed by two main waterways flowing into the bay, the Willow River and the Northflood. The Northflood is a strong, swift flowing river that crashes down out of the northern and eastern hills, rushing to the sea. The Willow River, on the other hand, winds lazily through the flat pastures and swamps south of the town. It is a broad, slow moving stream at this point, but its origins stretch far up  through Pleasantville into the high mountain valleys, and it claims many branches for its head, some as wild as the mouth is calm.
The Northflood rises quickly into the hills above the town, across the moors to Dassal and Waynesburg, the Golden Lake and beyond to Hillsburg in the far north.