Procedural Generation of a Hex Crawl Region.
Each region in your "game world" needs two things for it's inception: a starting settlement and a starting dungeon. OSR has produced a great deal of dungeons so you can just search for one someone has already written. You can either make your own settlement or use one of the Towns, Cities, or Villages I've made.
Once you have your first settlement, you add a road that goes through 2d6 hexes leading elsewhere. This road will serve as the backbone for the region. You can use the What direction does this Road go in table and the 1d6 hex direction table to make the road.
What direction does this Road go in? (2d6)
2  It abruptly ends (It's missing in this hex, but continues on past it) 
3  It exits the nearest clockwise edge from entrance 
45  It exits the 2nd nearest clockwise edge from entrance 
68  It exits through the Opposite Edge 
910  It exits the 2nd nearest counterclockwise edge from entrance 
11  It exits the nearest counterclockwise edge from entrance 
12  It forks (roll again for branch distance and what the branch ends in) 
Author's Notes: Roads are mechanically favored to continue in straight lines and shouldn't end up making loops within themselves. Personally, I really like the idea of roads having meaningful things on both sides and this way you also start with another known location and a way to reach it from the starting settlement. 
Now for what populates the end of the road you roll on the Road Destination table below.
Road Destination Table (1d10)
13  Village 
45  Town 
67  Natural Landmark 
89  Fortified Keep 
10  City 
Populating Hexes
So at this point you'll have One Settlement, One Road, and One Road Destination. You'll also have 2d6 hexes which need to be populated as well. The content of these hexes is determined by first classifying them as a Polite Land's hex or as a Wilderness hex. Polite Lands Hexes are the 6 hexes surrounding a city or the hex occupied by a town. All other hexes are Wilderness Hexes. You fill each hex by rolling 3 1d6's and then consulting the Tables below to determine their contents.
Polite Lands Hex Conent (1d6)
Wilderness Hex Content (1d6)
Populated Hex Filling (1d10)
Ruined Hex Filling (1d8)
Desolate Hex Filling (1d6)
Wet Hex Filling (1d4)
1. Consult the Table below to determine what kind of church it is
Church Alignment Table
2. Roads are 2d4 hexes long. After rolling for the number of hexes, roll 1d(Road Length) to determine which portion of the road this is. Then roll for what destination lies at each end of the road, and what direction the road travels in.
3. Rivers are 1d10 hexes long and are otherwise generated as roads without destination.
At this point you'll have a few roads leading to villages, towns, and possibly even a road to a different city. Now simply fill in any gaps around the roads hexes and add a border of single hexes around the entire region. For the border hexes do not roll for the length of any roads and rivers, these simply leads away and to another region
Now that we have a geographic hexmap, we need to add terrain for each.
Starting at the first hex you populated with your starting settlement, roll a 1d6 and go that many columns across the Hex Terrain Table to determine the starting terrain. For every other hex, use the Table to determine the adjacent terrain.
Hex Terrain Table (1d20)
Now that we have determined the terrain of each hex, we are able to add natural landmarks and monster lairs.
At this point you have a decently sized hex map filled with intractable items but you are limited with informing your players about it. There are a further four final things necessary for your HexMap to be completed.
1. Naming every road, river, and uniform unit of terrain
2. Drawing a map for your players
3. Adding Dungeons
4. Constructing a rumor table
While the first three are straightforward, here are my procedures for constructing a rumor table.
1. Each city gets 4 rumors, each town gets 3 rumors, each village and keep gets 1 rumor
2. Every named terrain region gets a rumor of what monsters remain inside
3. Each monster lair gets a rumor, half are vague the other explicit
4. Each Natural Landmark gets a rumor
5. Each Road towards a settlement in a different region gets a rumor
This should give you a decently sized region to hexcrawl through full of a variety of things for players to interact with and a way for them to become informed about the contents of the area.
Here is an example of a hexcrawl constructed using these rules.
13

Populated

4

Ruined

5

Desolate

6

Wet

Wilderness Hex Content (1d6)
1

Populated

24

Ruined

5

Desolate

6

Wet

Populated Hex Filling (1d10)
1

Lumberyard

2

Hunting Camp

3

Trading Post

4

Mine

5

Farmland

6

Village

7

Estate

8

Church ^{1}

9
 Bridge 
10

Roadside Inn

Ruined Hex Filling (1d8)
1

Lumberyard

2

Hunting Camp

1

Trading Post

2

Mine

5

Farmland

6

Village

7

Estate

8

Church ^{1}

9
 Bridge 
10

Roadside Inn

Desolate Hex Filling (1d6)
1

Road ^{2}

2

Sign/RouteMarker

3

Campsite

4

Fountain

5

Idol of Favor

6

Well

Wet Hex Filling (1d4)
1

Waterfall

2

River ^{3}

3

Stream

4

Pond

1. Consult the Table below to determine what kind of church it is
Church Alignment Table
13

Lawful Church

45

Neutral Temple

6

Chaotic Altar

2. Roads are 2d4 hexes long. After rolling for the number of hexes, roll 1d(Road Length) to determine which portion of the road this is. Then roll for what destination lies at each end of the road, and what direction the road travels in.
3. Rivers are 1d10 hexes long and are otherwise generated as roads without destination.
At this point you'll have a few roads leading to villages, towns, and possibly even a road to a different city. Now simply fill in any gaps around the roads hexes and add a border of single hexes around the entire region. For the border hexes do not roll for the length of any roads and rivers, these simply leads away and to another region
Now that we have a geographic hexmap, we need to add terrain for each.
Hex Terrain
Starting at the first hex you populated with your starting settlement, roll a 1d6 and go that many columns across the Hex Terrain Table to determine the starting terrain. For every other hex, use the Table to determine the adjacent terrain.
Hex Terrain Table (1d20)
Roll  Plains  Forest  Hills  Mountains  Swamp  Water 
19  Plains  Forest  Hills  Mountains  Swamp  Water 
1014  Forest  Plains  Mountains  Hills  Water  Swamp 
1517  Hills  Swamp  Plains  Forest  Plains  Plains 
18  Mountains  Hills  Forest  Plains  Hills  Hills 
19  Swamp  Mountains  Swamp  Swamp  Mountains  Mountains 
20  Water  Water  Water  Water  Forest  Forest 
Author's Notes: Assume water terrain hexes to mean coasts, deltas, and lagoons rather than open sea. Seas and Oceans are only added by Towns and Cities with ports. 
Example of how the table works:
After fill a Hex with the Plains terrain, you would want to fill the the terrain of the surrounding hexes. Going clockwise starting at the flat top of the hex you assign each surrounding hex a terrain type. Lets say you go From Hex 0,0 to Hex 0,2 You would roll a d20 five times and what ever terrain is rolled is the terrain of that hex. Let's say we rolled the following 11,7,15,6, and 2. This means that around this hex are hills, forest, and more plains.
Now that we have determined the terrain of each hex, we are able to add natural landmarks and monster lairs.
Natural Landmarks
Count the number of hexes total in your region. Roll a 1d12 until you have a sum equal or greater than that number, that is how many natural landmarks are present in the region. For example if you have 21 hexes in your region, you would roll a 1d12 a number of times until the sum of your roll equals or is greater than 21. Lets assume that you had rolled the following: 10, 4, 3, 2, and 5. That's 5 rolls which means there are 5 natural landmarks in this region. Place them where you feel is appropriate.Monster Lairs
Each wilderness hex has a 1 in 6 chance of having a monster lair within it. Polite lands are free from monster lairs.
Final Touches
At this point you have a decently sized hex map filled with intractable items but you are limited with informing your players about it. There are a further four final things necessary for your HexMap to be completed.1. Naming every road, river, and uniform unit of terrain
2. Drawing a map for your players
3. Adding Dungeons
4. Constructing a rumor table
While the first three are straightforward, here are my procedures for constructing a rumor table.
1. Each city gets 4 rumors, each town gets 3 rumors, each village and keep gets 1 rumor
2. Every named terrain region gets a rumor of what monsters remain inside
3. Each monster lair gets a rumor, half are vague the other explicit
4. Each Natural Landmark gets a rumor
5. Each Road towards a settlement in a different region gets a rumor
This should give you a decently sized region to hexcrawl through full of a variety of things for players to interact with and a way for them to become informed about the contents of the area.
Here is an example of a hexcrawl constructed using these rules.