
This post began life as an attempt to redesign the Ranger for 5e. I’m still going to do that, but it diverted to an explanation of my wilderness hexcrawl procedure, which I don’t believe I’ve ever shared online in full.
I am on record as saying “exploration” is everything the players do that isn’t talking to people or fighting monsters, but for the sake of this, we’re going to focus on wilderness “exploration” and parts of the game that use that.
So to do that, we need to talk about what this looks like in my game and at my table. All overland travel in a dangerous area is on a 6 mile hex grid, and we engage in the “gritty realism” rest variant when we use it. This means a short rest is 8 hours overnight, and a long rest is every 7 days/short rests or if the party spends 24 hours within the same hex (which also puts them back on “normal” resting; unless, of course, they travel outside that hex again). Again, this is a “dangerous area,” which is most of the parts of the world that adventure takes place in. If the players are travelling a long distance that isn’t the focus of the adventure (for example, they travel weeks from the city of Dawnharbour to the city of Steelhaven) then that can be handwaved; they’re sticking to roads and not worrying about it, because the Adventure is not The Travel.
When the party travels through hexes, we determine their planned route and weather. This determines how many hexes they can go through. The party can travel 24 miles per day through normal terrain, which equals 4 hexes; difficult terrain like swamps, deep forest or mountains may reduce this to 3 or even 2 hexes.
For each hex, the players roll what I call “Advancing d6s.” This means they roll, in order: 1d6, 2d6, 3d6, and finally 4d6. This produces several results, between 1-6, 2-12, 3-18 and finally 4-24. This corresponds with this simple table:

The d6 table is landmarks such as burial mounds, obelisks, etc. The d8 table is several encounters that are not necessarily combat related, such as a group of fake adventurers, a Peryton that attempts to capture a player, or a golden Fey steed appearing on the horizon. It also contains an entry called “Character Event,” which is a series of encounters built around the PCs. (I’ll go more into Character Events in a later post.) The d12 table is larger landmarks and mini-dungeons or lairs, including things like wild magic zones, dead magic zones, etc. Finally I have lists of combat encounters. Embphyrkhaksis is the BBEG of the campaign this particular table is taken from; an adult red dragon who can appear any time all four players roll 6s. (For each encounter with Embphyrkhaksis, I raise the threshold for him to abandon the encounter by 10hp; initially they just had to deal 10 damage to the dragon for him to flee, but after 4 or 5 encounters they need to do 40 or 50 damage for him to leave. Exciting!) I then arrange the encounters we rolled into the best narratively cohesive order, based on my judgement as a DM and my absolute, flawless, omniscient knowledge of what is Actually in the hexes ahead of them; I ignore results that are boring or have been used recently if there is a legitimate feature in a hex that I’ve previously determined.
At a later time, I’ll update this post with a formatted PDF of my table so you can alter it and make your own.
When the party spends the night in the wilderness, they need to set up watches. My rules assume a 4 person party using 2 hour watches. (Elves can take 2 watches and still gain the benefits of a short rest.) During a watch, they roll 1d6; on a 6, an encounter happens. The character makes a Perception check to see if they notice the encounter; this is contested against a DC equal to a passive stealth check made by the monster. (If there are multiple monsters, I use the monster with the highest bonus.) If they fail, they are Surprised, which can be really dangerous with ¾ of the party still sleeping, outside of their armour. If they pass, the party member has the opportunity to wake up the other players and put on their armour. (Realistically, this takes 10 minutes, but the start of the encounter is a little abstracted in this case.)
This is the core of my wilderness overland travel system. It’s easy to see, when it’s laid out like this, that there are several “hooks” by which the Ranger can key into to make them feel very useful in this style of campaign.