First, think about where the players currently are, what they could do there, and where you want them to go next. Let’s say they are currently in a city and have to find a dwarven hermit in the dreadful mountains, they might need a guide or maybe they want to buy climbing gear. It would be cool if they met a dwarf living in the city that tells them about the hermit, some interesting backstory of why he is not with his clan. It will help the characters look forward to the hermit, Trekor Rockslide is no longer a name they have heard from the last NPC they met. It’s now a name that has been mentioned twice, the hermit will feel more real, he is something that exists in this world.

So the session starts in the city, having lots of NPCs talking with the players. Then they should go to the mountain range, is there a forest between the mountains and the city? Are there monsters inside it? Think about what would make this traveling part interesting. The players just talked for the last 30-60 minutes, what would bring a nice change of pace? Let’s say they are ambushed by wood elves who want to defend their forest from intruders, they are not hostile but appear to be ready to release ten arrows into the players at the first sign of aggression. The players can decide to fight them, or convince them that they mean no harm. The elves should not be an invincible force. Always prepare that the players will at least think about fighting every encounter you throw at them.

After they dealt with the elves they arrive at the base of the mountains. They will have to climb at some points, make them roll a few checks to see if they succeed without problems. Make it easier for them if they bought climbing gear in the city. You could plan an alternative encounter with some mountain bandits or monsters if the players resolved the wood elves encounter peacefully (some groups will yearn for at least one combat per session). And finally, maybe after a night’s rest in a cave, they meet Trekor Rockslide, the hermit that can help them finish their quest.

Usually, I want my session to end on a hook for the next session, I want to give them something to think about. Otherwise, you might have disoriented players at the start of the next session. In my example the players could have finished the rest just to have Trekor appear in the morning, mysteriously standing in front of them as the first sunshine begins to light up the cave. Or if you still want to play a little longer you could have him talk to them, explain that their quest is more than they think, they have to stop a great evil before it’s too late, you could reveal something big. And before the players spike Trekor with questions you end the session. But be aware, using cliffhangers every single session will be exhausting, if you use them too frequently the players won’t care about them anymore.

Written out Example

Here’s an example of the session I would have prepared in this blog post. As you can see there is a lot of space between the notes for improvisation. I roughly estimate this notes to last for about 4-6 hours of actual play time.

Last session the party arrived in the city of Timbershield (farmlands around, lots of trading with food, many lower class citizens). They want to search Trekor Rockslide (Dwarven Hermit, 276y old, bald, braided grey beard, harsh exterior but good of hearth), a dwarf that fought the red dragon Chaldrus 100 years ago. He can tell them about the dragon’s lair and his weaknesses.

In the city they can buy climbing gear, there is a potion shop with potions (only rarities common-uncommon). They meet a dwarf named Umnan Oakbeard (Farmer, 120y old, filled with bitterness and pessimism) he tells them that he met Trekor a few times and the hermit has gone insane, he talks about a prophecy, the dragons will unite and destroy the world. Trekor was a respectable member of dwarven society, he was chosen to defeat Chaldrus the dragon but left the clan afterward, seemingly the encounter changed him a lot.

There are a lot of thieves and beggars in the city, maybe someone tries to steal something from the players if the moment is right (>16 Passive Perception check to notice).

A few hours walk outside the city an elven forest begins, the wood elves are skeptical of outsiders and will ambush them, asking what they want, trying to get rid of intruders as soon as possible. They got orders to first try to talk peacefully (DC 15 Persuasion Check to convince the elves to let them pass), but they won’t hesitate to attack if any player talks about damaging the forest or harming animals inside (even if it’s said jokingly). Up to 8 elven archers (Scout stat block) attack, if at least 2 are slain, the elves retreat and leave the party alone.

If the party fights the elves, they will retaliate as soon as the party rests inside or just outside the forest. If they resolved it peacefully, the elves help them get to the mountain range quicker and share their food with them.

To climb the mountain the players will have to succeed on three climbing checks (they have Advantage on the rolls with climbing gear). DC 13 Athletics Check => 2d4 bludgeoning damage on a fail DC 16 Athletics Check => 5d4 bludgeoning damage + 1 exhaustion level on a fail DC 14 Athletics Check => 3d4 bludgeoning damage on a fail

If they make a lot of noise, they could attract bandits (1x Bandit Captain, 1x Archer, 5 Bandits).

At the end of the day they should meet Trekor Rockslide, he either comes to them or they have to find him, depending on where and when they rest.

Trekor Rockslide will tell them about a prophecy. After fighting Chaldrus 100 years ago, he nearly got burned alive. He managed to jump into a river and survive. His wounds were really bad, thus he was in a mixed state of sleep and being awake, after a day he started to have a weird vision about more dragons, about burning cities. He saw a volcano, which contained the heart of fire, a legendary artifact that allows one to take control of red dragons, they have to take every command from the wielder of the artifact. Trekor wants the characters to travel to the volcano and save the world.

Below you can see example notes for a dungeon I prepared which allowed for about 7 hours of playtime.