This article was last updated on December 12th, 2023.

Five big tips about level 1-20 D&D

In 2022, I wrapped up a three-year Dungeons & Dragons campaign which saw characters go from level 1 to 20. At the end of three years of running an (almost) weekly D&D game, a few takeaways stand out.

1. Building around the characters creates a cohesive level-one-to-twenty experience.
2. Even though we are playing through an epic multi-year campaign, a focus on the next session helps keep the game’s pace sharp.
3. Regularly check in with the players about their feelings about the game.
4. Embrace deadly monsters. D&D characters are powerful, and in a 1-20 campaign we can dig deep into the Monster Manual and beyond to challenge players.
5. Keep a story log which documents the adventures of the level 1-20 experience.

1. Build around the characters

In a level 1-20 campaign, we as the DM face one central challenge: How do we keep the players interested in the same characters for years? A few things have helped me keep the players (mostly) hooked on the unfolding story and the same characters over three years: milk characters’ backstories, vary the villains, follow the players, and make interesting magic items.

1.1 Use character backstory

The good thing about witnessing the same characters for three years is, we have time to explore their backstories. We can dig deep into each player character’s background, their motivations, their rivalries and alliances.

Whether we’re running homebrewed adventures or follow a published campaign book, looking for ways to tailor the current content around the characters can help keep things interesting over a long-running campaign. While preparing for the game, we can take some time to think about ways in which the characters might be connected to the current adventure. Could someone know the villain? What if the stone giants in Storm King’s Thunder are actually enslaving the tribe of wood elves of one player character? Personalizing the adventure hooks for each arc of the campaign creates drama. It puts the characters front and center of the story, and keeps players interested in playing them.

1.2 Follow the players

Players do strange things. They decide to rescue NPCs which were born off of a list of random names just seconds earlier. They tunnel-vision onto locations which have nothing to do with the current adventure. But again, we have time in a level 1-20 D&D game, so we can afford to follow the players’ interests. If they want to save Gellert the fishing ogre, let them get a boat, throw an appropriate monster, such as a water elemental into the mix, and watch Gellert become a major NPC in your campaign.

Following the players’ interests is a constant balancing act between what we have prepared and what emerges during play. In my experience, erring on the side of what the players focus on sustains the interest in a long-term D&D game of both the players, and the DM.

1.3 Vary the villains

It’s tempting to come up with one epic villain, and have the characters oppose this villain for 20 levels. However, even fighting different types of minions, servants and cultists of the same villain becomes tiring. We can still foreshadow major high-level villains from the first levels on. But we should keep things vague enough to leave room for discovery later on. Instead, running different villains for every couple of levels, keeps the gaming experience fresh. A major villain every four to five levels can work well.

If you are looking for villains to include in your game, we have published a number of PDFs with NPC villains built on class archetypes. Check them out here: Illusory Script on DMsGuild.com.

1.4 Make interesting magic items

D&D characters get a lot of abilities over the course of 20 levels. But some of the core class or species features stay the same throughout the game. Making weapon attacks, casting cantrips, or channeling divinity all stay more or less the same from tier one (level 1-4) to tier four (level 17-20). Therefore, giving each player magic items that are tailored to enhance the character’s arsenal can be a way to inject new and unexpected mechanics into the game.

For a level 1-20 campaign, custom magic items which grow in power over time are a great way to keep tweaking the same core magic item of a character. The monk’s Arcstaff keeps unlocking more storm-based attacks, while the moon druid’s Mantle of the Oakwarden develops powers to both protect her allies, and punish her enemies. These items can grow with the character. And unlocking new powers can become part of the story of the campaign.

2. Focus on the next session

The larger stories we are telling in our level 1-20 D&D campaign can span months of real-world time. But the current adventure determines how your players experience the game. That’s why, whether it’s a one-shot or the 86th session in your level 1-20 campaign, when we focus on the game ahead, we focus on what’s most important for the gaming experience.

Mike Shea from slyflourish recommends thinking “two horizons out.” That means we firstly focus on what’s immediately ahead. For example, the characters’ crawl through a dungeon. So we think about the rooms, the monsters, the NPCs, and the lore of the place. Secondly, we think about what comes after this immediate horizon. The characters will learn about the dungeon’s connection to the court of the shadow fey, so we can think about what might await them there.

This is thinking two horizons out. And even in a campaign that spans months or years to complete, a focus on two horizons out keeps us thinking about what actually matters when we sit down to play.

Similarly, we can keep things fresh in a long-running campaign by running breather or filler sessions.

3. Check in with the players regularly

If we want to keep the same game with the same people going for years, we need to keep track of how everyone feels about the game. For me, asking players for stars and wishes at the end of a session to learn what they liked and what they want more of is an easy way to get short-term feedback. After longer campaign arcs, we can do a more in-depth survey to get a more detailed view of the player’s feelings about the campaign.

To keep everyone entertained, and wanting to come back week after week, we as the DM need to react to the desires of the players. Regular check-ins through conversation or more formal surveying helps us keep an eye on everyone’s mood concerning the game.

4. Embrace deadly monsters

Over the course of playing together with the same characters for months or even years, players develop strong synergies. They know how to play off of each other’s abilities, and become more powerful than their individual levels suggests. Therefore, if we want to challenge players in combat in a level 1-20 campaign, we need to embrace deadly encounters. On paper, an encounter might seem obviously deadly. For example, a CR 16 marilith has seven attacks and one reaction per turn. We might think this is obviously going to kill some of the level 7 player characters. But the players know that the sorcerer can dimension door them out of danger if necessary. The monk might stun the marilith, entirely depriving it of any of its attacks.

Players become better at using their characters in combat when they play together for weeks, months, or years. To keep challenging them, we can often push things past the flashing red “DEADLY” sign that lights up when we do our encounter balancing.

On way to do this, is to look to other monster books. Here are some of my favorite ones: My Favorite D&D Monster Books.

5. Keep a story log

If we’re running over a hundred sessions in a campaign, it’s easy to forget what happened. To keep the big picture in our DM head, we can write a short entry summarizing each session. This doesn’t need a lot of detail. One or two paragraphs for a three-hour session is enough. Here are a few tips for keeping a story log:

1. Write the entry quickly after the session, ideally within a day of running the game.
2. Give each entry a flavorful title, like the title of a TV show.
3. Note down the in-game dates of the events that took place in the session. (Write down the real-world date of the session as well if you want.)

We can use this running story log to refresh our memory before preparing for the next session. And at the end of the campaign, the log makes for an entertaining, nostalgic look at twenty levels of adventure and drama. For reference, the log for my level 1-20 campaign amounted to over 80 pages of written summaries.

Level 1-20: an epic D&D experience

Running a D&D campaign for three years, watching the characters grow, their bonds tighten, and the story unfold, has been an awesome experience. The emotional investment of DM and players required to complete a level 1-20 game, creates an intense sense of epic adventure. To keep things interesting for this long, build around the characters, focus on the next session, get player feedback, don’t be afraid to throw seemingly deadly encounters at the party, and keep a written log of the story.