The Dragon's Pit dungeon and boss are the key to a brutal boss fight and area, and are a necessary step towards something great. The boss also drops a fantastic DLC weapon that can help you on your journey through the Lands of Shadow. Here's how to beat them.
Elden Ring Shadow of the Erdtree – Walkthrough Part 1: Gravesite Plains
To reach the Dragon's Pit dungeon you need to teleport to the Castle Front Grace and immediately go right. Follow the path to the large Pillar that should appear on your screen. Once you reach the Pillar Path Waypoint Grace just before the large structure, do not go up. Instead, go right where an annoying, angry NPC will be yelling. Talk to them for the great voice acting and writing and continue straight on your path.
Before the dungeon you should be invaded by the Ancient Dragon-Man. Fight him, this is not the real boss! Keep moving forward after you defeat him and enter the dungeon which should be on your left.
The dungeon itself is very short, but filled with formidable enemies that can knock you out with a single blow, even with 10 Scadutree Blessings.