Old‑School Greyhawk, New‑School Thrills: A 5E Workshop

Old‑School Greyhawk, New‑School Thrills: A 5E Workshop

Mordenkainen and Tenser. Tasha and Vecna. You know the names, but have you ever experienced their world?

TYPE

One-Shot

SYSTEM

Game Master Workshop

LANGUAGE

English

EXPERIENCE

Open to all

AGE

18+
10 SEATS LEFT
$20.00

/ Session

Details

Once / Sunday - 9:00 PM UTC

Jun 28

Session Duration / 1–2 hours

2 / 12 Seats Filled

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Schedule

Sun, Jun 28 | 9:00 PM

Meet your party members

2/12

About the adventure

This is a webinar/class, not a game session! Greyhawk has always been a world of frontiers—wild borders, crumbling empires, and mysteries older than the maps that claim to contain them. In this workshop, we’ll explore how to bring that classic, dangerous energy to your 5E tables without rewriting the entire ruleset. You’ll learn how to capture the tension, scarcity, and player‑driven exploration that defined early Greyhawk play, while still giving modern players the clarity, pacing, and spotlight balance they expect from 5E. Together, we’ll break down the core pillars of old‑school Greyhawk—factions, friction, and the unknown—and translate them into practical tools you can use immediately. From reaction rolls and morale checks to rumor webs, wilderness clocks, and consequence‑driven worldbuilding, you’ll see how small mechanical shifts can completely transform the feel of your campaign. We’ll also look at how to adapt classic modules and regions of the Flanaess for today’s players, preserving the danger and weirdness that made them iconic while avoiding the pitfalls of outdated design. You’ll watch a live encounter conversion, walk through a case study of updating a classic Greyhawk adventure, and learn how to create a living world where factions remember what your players do—and what they fail to do. Whether you’re a veteran GM looking to deepen your craft or a newer DM curious about old‑school playstyles, this workshop will give you the tools to run Greyhawk with confidence, clarity, and a sense of wonder. If you’ve ever wanted your 5E games to feel more dangerous, more mysterious, and more alive, this is your invitation to step into the Flanaess and rediscover what made Greyhawk legendary.

Meet the Game Master

5.0

(4)

Teacher/Educator

Less than a year on StartPlaying

1 game hosted

Highly rated for: Storytelling, Creativity, Teacher

About me

I've been playing D&D since long before D&D was cool. I got my start in the late 70s with the Basic box set, which at that time included module B1, In Search of the Unknown. I prefer to DM and have run every version of D&D since Basic/AD&D. I mostly run 5E games but also enjoy ShadowDark. My longest-running D&D campaign, set in the World of Greyhawk, has been running for 10 years now and is still going strong. I try to combine the best of Old School and Modern in my games, from dungeon crawling to diversity and inclusion.

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Character creation

Creating your character

This is a webinar/class, not a game session! No character creation required.

What to expect

Preparing for the session

Although this is a webinar/class, not a game session, I plan to run the session on Roll20, as I will be using a number of interactive examples.

What Kyle brings to the table

I am officially an Old Greyhawk Grognard! I have been playing (and running) Greyhawk since 1E. I will bring both nostalgia and experience, as well as an openness and appreciation for the many benefits of "new school" styles of play. I'm also here to learn from YOU.

Homebrew rules

Although this session is focused on 5E, I have been playing (and running) Greyhawk since 1E. I will discuss a number of old school and other alternative rulesets to 5E, too. Mix and match to taste!

Equipment needed to play

Internet

Computer

Microphone

Safety

How Kyle creates a safe table

Although this is a webinar/class and not a game, I will be discussing the good, the bad, and the ugly of Greyhawk. As this session will be hosted on Roll20, we will have the advantage of built-in safety tools, such as X, N, and O Cards.

Content warnings

Seminar

Safety tools used

Frequently asked questions