Reward: Son of Chesty, 100,000 gold, Diamond of Sorrow
Before starting this you need to have around 230,000 gold, give or take 5000. When you collect the required amount of gold travel to the tower where you will face some enemies and a Spire Shard, the shard is easy to kill if you use magic and keep your distance. After you fight them off, go up and buy the Bloodstone Tower. Go to the stop, you'll pass by the Cullis Gate that is supposed to be wrecked, and go to bed.
You'll dream of being a child again, walk up and open the chest ahead of you. Read the note and follow the trail another chest, open the second chest and read the note. Kill off the group of monsters it spawns. Make your way back and open the third chest, the Hobbes you'll face seem big and strong, but only seems that way because you're a child again. After you kill them follow the quest path to another chest and open it.
After you've killed the Hollow Men follow the trail again, to your right after the gate is a statue, mimick its expression and go to the next chest. A banshee will appear, kill it as you normally would by defeating the minions then slashing at it. Keep going after you're done that. If you go off trail to your right there is a house with a chest (the good kind) in it. Continue and open up the next chest, fight the Balverines. Open the chest again to receive your prize and go back to the bed.
Welcome back to reality.