Location: Astos (Country-As-Dungeon)

 This is another experiment in overland travel procedure. Wise voices have remarked that in many ways we want the same sorts of things from an overland journey as we want from a dungeon-crawl. To get my head around this idea, I've designed a map for a country, as though it were a dungeon with twenty areas. The connections are more approximate than for a dungeon, and I'm sure there are many tweaks you'd have to make to the normal crawling procedure to make it work well. This is all untested, a quick mock-up to get my head around the idea, but it's already throwing up all sorts of questions for me. Adapting "empty" rooms, special areas, monsters, traps, and treasure really got my creative juices flowing.

I guess you'd want to say that characters don't heal any HP while they travel, as that rather deflates the danger when travel takes so long. On the other hand, if someone has a healing spell they can cast every day, I suppose that would really change up the math of HP attrition. It makes sense that the DM should set the scene of any encounters such that they can often spin off into further scenes at the normal, personal, minute-to-minute scale. That way, players won't get used to the idea that it's safe to use all their daily spells and abilites right away in every overland encounter. You'd also want to figure out how rationing, foraging, and other concerns are reckoned, which I have helpfully not done to leave it as an exercise for you.

Astos

The kingdom of Astos is a synthesis of post-LoTR fantasy doorstopper influences like Wheel of Time, the Inheritance Cycle, and the Kingkiller Chronicle. It's one of those nominally calm and cheerful lands that doesn't understand the peril it is slouching into, helped along by agents of a Shadow or Dark One or what have you. Like many dungeons, it has a few factions— the secretive conspirators against King Alerholt, the idealistic servants of the crown, and the elf-friends, ideologically aligned with the crown but disillusioned with the king and the nobility.

1 Turn represents about a week of travel, and covers a region or about five squares, assuming the party is moving carefully. Travel will be slower when they check out points of interest, get especially encumbered, brave the winter, or face inclement weather.  Travel will be faster when they ride fast mounts, rush heedlessly, or are aided by the terrain.

Little ford symbols and door markers represent natural connections between regions. If they are connected, a party can enter at any reasonable point; they don't need to first journey to the spot on the border that has a door symbol. Some regions don't have a natural connection. At the DM's discretion, entry can still occur, though it will take 1d4 Turns. If the party has guides to the area, they can roll the die first and then decide if they want to attempt it.

2d6 Random Encounters (1-in-6 every Turn)

2. 1d10 undead shadow-warriors. Their cursed swords prevent healing and drain 1 hp per day. Those slain rise a week later as shadows.

3. 2d10 2 HD monstrous humanoids who serve an even freakier 8 HD monster

4. 1d100 con artists, brigands, or pirates

5. Heavy rains slow travel. Roll another encounter check.

6. wildlife-- roll a d4: 1. 2d6 wild dogs, 2. herd of deer, 3. spying pigeons, 4. boar

7. Faction encounter: spies, knights, or weary elves

8. Corrupt or inept official

9. Peasant who offers help (on negative reaction, duplicitously)

10. Doomsaying prophet (high-level cleric, reaction roll determines alignment), 25% of a mob

11. 3d10 skeletons

12. Rotnem, a surly yet wise immortal dwarf wizard whose personality was mangled by a curse.

Areas

1. Morcanor (Elf-Friends): redoubt of elven scholars in a grand gully hidden in the heart of a forest, called by outsiders Morcanor's Woods. Their rugged custodians, called "Elf-Friends", tend to cordon them off from interlopers, as they are credulous and fragile. PCs will be intercepted by an Elf-Friend patrol (stats as brigands). On a negative reaction roll they will drive the PCs off with bows and pen-knives. On a more positive roll, they'll tell them to beat it more nicely. If you can actually get into Morcanor, the elves can tutor magic-users, identify magic items, or confer +1 arrows and polearms on those they charge with a solemn quest. These elves are distinguished by their pastel robes, wispy hair with sap-scented oils, maypoles, and love of dance. The captain of the Elf-Friends here is the aging surveyor Vortins.
2. Tewse Marsh (Elf-Friends): peat harvesting villages, dilapidated gallery roads, and spooky trees. Slows travel. A horrific meat-grinder of a battle from last generation's war hangs like a spectre over the people here, and wishful indigents sometimes dive for treasure that they know isn't really there. Cockscomb hats and falcata are in fashion here.
3. River Guimri (conspirator): a meandering, steep-banked river that slows travel unless you buy passage on a fast boat (30 gp/Turn). The fish here are inept, and "Guimri fish" is an insult across all of Astos.
4. Limondy (Crown): a woodcutting region, known for its vineyards and fine hounds. Of late, a strain of shaggy black hounds have escaped captivity and mingled with wolves to birth a race of murderous freak-shucks. PCs visiting Limondy can purchase un-freaked hounds, as well as expensive wines that function as potions of certain spells.
5. Orcarad (Crown): the lands overseen by the lady knight Orcarad, chapter master of the knights of St. Nilte. She shelters "true" allies of the crown who are increasingly out of place in the capital at Silat, as well as renovating the order's main chapterhouse. Fighters who swear an oath of loyalty, pass a few trials, and keep an overnight vigil can be inducted into the order here, receiving a horse and a unique coat of arms as well as the following blessings ot Saint Nilte: to heal another with a touch for [level]x2 HP once per day, at 3rd level to constantly be affected as by protection from evil, and at 5th level or higher cast cure disease once per day. If they seriously break their oaths they will lose these blessings, and upon their fellows learning this they will be barred from the order. The common people of Orcarad are mostly engaged in ranching, and known for colorful quilted cloaks as well as their tolerance of witches.
6. Liorlin Fields (none): wide, rustic spaces with small trade towns along the rivers. Renowned for their wool clothing and tobacco, which they sell at a suitable price. However, if you go even further into the remote hamlets where the tobacco is grown and sheep are shepherded, you will find the salt of the earth, an insular but straightforward folk descended from the demigod Addartas. Not only are their goods sold for a great deal, but any hirelings picked up here get +1 HD, proficiency with bows and clubs, and a [level]-in-6 chance of comprehending ancient languages, a fact that will surprise and concern even them when they discover it.
7. Fog Lake (Conspirators): crossed by ferries and barges (5 gp a head), but infested by freshwater sharks, servants of the Dark One.
8. Lake Vale (Elf-Friends): an ancient forest with overgrown paths, old stone pillars, and root-banked ponds. Slows travel. Legends claim that the first king of Astos, Lenregne,  lingers in these woods, promising to return in the realm's greatest need.
9. Caivret (Crown): a province ringing a town of banking and law, and the royal family's summer holdfast. There lingers Princess Margane, forced into a sort of semi-exile for attempting to reverse the evil law of her father's ministers. While loyalist forces attend her, she privately confides in her bodyguard, the half-elf Llad, that she has begun to wonder if the monarchy is worth keeping around at all. Unbeknownst to her, there are agents of the Shadow in her coterie, and at the first sign of her striking out against their master, such as if the PCs convince her to help them in some great quest, assassins will poison her and her guests at the next meal. The province is known for its many-colored fields of flowers and the propensity of its people to gamble on anything.
10. Barrow Hills (Elf-Friends): grassy, stony hills often studded with ancient barrows. One hill, called simply Elf Hill, is sometimes seen to have clouds of mist emerging from its elf-glyph-covered barrow mouths. This comes from a gateway at the center of the barrows in that hill that serves as a portal to Morcanor. The warm air of those woods combine with the barrow chill, and thus produce mist and fog. Those who walk through the gateway find themselves in a still grove near the heart of Morcanor. The elves will probably be pissed with them if they find out.
11. Laigal (Crown): semi-lawless series of towns, taverns, jealously guarded orchards, and military camps in the outlying lands around Silat. Locals are hostile to anyone who doesn't match their idea of a proper Astosian. -3 reaction unless you're a Laigali, cleric, brewer, horseman, or mother, and encounters are met on a 3-in-6. Despite everything, they are emphatic patriots. The closest thing to an authority in the region is the Cohort, an organization of professional firefighters/burglars. Their hideout conceals a vast treasury, including some cool spell scrolls and Matagot, a blackened +1 intelligent dagger with a tiger's eye in the hilt that can see through invisibility. It has a feline personality, which has led to some questions around the captain of the Cohort's sanity.
12. Silat (Conspirators): capital of Astos and the seat of King Alerholt. Unfortunately, a den of vipers managed by sycophants and liars only meaningfully opposed by street gangs that sometimes riot against the more draconian policies enacted in the king's name. Anything the PCs might do here that sets them out will be met with interrogations, extorted bribes, and/or surreptitious deportation into Laigal. Alerholt's chief advisor, Malise, is a rube, controlled by the palace's butler and spy for the Dark One, Teird.
13. River Black (Conspirators): wide, deep river that speeds travel if you can secure a barge (20 gp/Turn, rustic) or passage on a river boat (50 gp/Turn, ritzy, secure). Near the headwaters of the river are the ruins of the Black City, a walled series of cyclopean streets and leaning towers. Within is an ash-covered woman in a black robe who calls herself the Patroness (Stats as ghost). If she can get a rube to take something she gives them out of the Black City, it will cause their soul to fester. They'll get grouchy, refuse to part with their gift, and lose 1 wisdom per Turn. At 0, she will hatch from the victim reborn, with stats as a death knight and an eye to conquest.
14. Sorrow (Elf-Friends): abandoned gnome towns in scenic birch woods. It is said that they left when a compact forged with them was broken by the king of Astos. Hidden in each town's well is a secret tunnel that leads to their hideout, for their departure was feigned. They are suspicious of outsiders, but are lifelong friends. Once they played drums and sang, but now none dare. Remarkable for their pointed navy caps, coracles, and brandy.
15. Kevalrigme's Gap (Conspirators): rough climbing through the barest and narrowest mountain pass. Impassable for horses, but mules can just about manage it. In the winter months, the thick icicles that form hanging from ancient stone arches along the "path" render travel practically impossible. The wizard Kevalrigme's country starts on the eastern side of the mountain, and he knows how to conjure winter storms out of season.
16. Pello (Elf-Friends): windy, windy, windy plains. Did you think you could cross the flatlands without much hassle? Wrong! Much hassle! Travel is slow and loud, and unless you have a ranger or something in your party you might emerge from the plains 1d90 degrees off-course.
17. Danbrangoire (Conspirator): soybean farmers and gardeners, the descendants of the Cognomen survivors of Tadyffire. Hidden in attics and cellars are valuable mechanisms, strange weapons, and clockwork creatures. Unwholesome and poisonous gasses sometimes float down from the Cognomen ruins in the mountains (1-in-6 chance per Turn), and those who breath them in must save vs death, getting a mutation on a successful save. The ancient Cognowoman Langwain seeks to gather an expedition to retake Tadyffire.
18. Tadyffire Gate (Conspirators): the ruins of a city that ran under the mountains, a wonder of brass and fire. The Cognomen once facilitated trade between Astos and its neighbor across the mountains, Hest, but some great doom befell them and none have managed to solve the child-grade riddle on the gate to pick through the ashes. Someone who manages it will find a dungeon-type environment populated by salamanders who have repurposed the great machines to their own uses, but may find the route through to Hest, a region of free towns, renowned falconers, and gregarious river magicians.
19. Amber Coast (Crown): the last prosperous province of Astos, a breadbasket so fertile that its stiff-necked city-slicker ruler, Count Brover, can't mismanage it so badly that the gold doesn't come rolling in. As long as we get a spot of rain soon. The pub is the center of public life here.
20. Grand Port (Conspirators): once a great trade port, now much diminished by the slow worsening of the world. Very few ships come into the bay from foreign lands these days, and even fewer head out. Many of the remainder are unsuccessful second-generation buccaneers, and PCs are liable to encounter 1d20 of them soon enough. Grand Port sits between the coast and the southern extent of the mountains, and serves as a gateway to the Hestian hinterlands.