Once again, start by lighting the bonfire here before moving on to grab the large soul off to the side of the path. From here just find your way down to the lowest level where some enemies are waiting. Defeat them and check behind the overturned carriage to the north for an Alluring Skull.
A little further ahead is a group of something, one of which is asking you to grant him death. Seek out the source of the voice and talk to him. Accept Yoel of Londor's services then check amongst the group of undead for some Homeward Bone
Run all the way back to the other end of the path and pull the lever to open the gate. Moving on, you'll find another bonfire, light it and rest if you want. Or you can go back to the Firelink Shrine and look for Yoel. He can level up your character as well as sell you items. He'll also hand you a Beckon the first time you speak to him at the shrine.
Anyway, back to the Undead Settlement, continue onward into the house where you can cut down one of the hanging things for a Small Leather Shield. And further below is corpse carrying some Charcoal Pine Bundle. Exit to the balcony and cut down another one of those hanging things, before circling around to the end of the balcony for some Repair Powder. Leave this house through the exit at the lowest floor. Push forward, grab the Loretta's Bone nearby before going further and taking a right into the stables at the end of the bridge. Beyond it is a door you can open to score a Caduceus Round Shield. Now if you remember Greirat did ask you to find Loretta, and you did only she's no longer alive. This completes Greirat's quest and he'll let you keep the ring as well.
Cross the white stone bridge and explore the area beyond to pick up some loot including some souls and an Ember. Search the bottom level for a ladder that leads into the sewer. The giant rat enemy here drops a Bloodbite Ring so try killing some when you get the chance. Climb the ladder at the end of the path and open the nearby gate to exit.
Cross the bridge here and light the bonfire so you can rest, or even warp back to Firelink Shrine if you like. While you're here, a message pops up stating that Holy Knight Hodrick is invading. This enemy is AI-controlled and not another player. He can cast healing spells in addition to his powerful sword attacks. Try to cut him off from the healing orb that he summons while keeping close to it yourself. Defend and counter as usual until Hodrick is defeated. You'll receive a Vertebra Shackle for winning, which will come into play later. Proceed up the path opposite of where the invader came from, and you should see a house in distance teeming with bad guys. You'll want to wait a while until some projectiles drop in from somewhere. This will kill some of the enemies, clear out the shack, go upstairs and back outside.
There is a closed door next to you that can be opened where a big powerful enemy is waiting. This is where the game starts getting real nasty and you can expect to die a few times. Although sometimes she doesn't spawn so good for you if you get lucky here. Otherwise if you see her near a pit to the side of the path, throw projectiles like knives to push her off for an instant kill. Explore this area for a bit if you want, just to get some loot and stuff. I just don't recommend venturing out too far though because the bad guys can give you quite a beating at this point. So leave that out for later. Instead turn around out of that door you opened and head for the big open area at the other side to fight the Curse-rotted Greatwood. Make sure you have a good supply of Firebombs before you fight this boss though.
Boss Battle - Curse-rotted Greatwood
This boss is undoubtedly huge but its arsenal is also quite limited and the range is poor, so it won't have much to hit with from a distance. What you need to do is target those sack-like things all over the tree's body. The first cluster of these should be easy enough to hit so attack them until they pop; keep an eye out for the tree's attacks while you're this close though, as they do a lot of damage. The acid will chip your health when you're standing on it too. Anyway, once the first cluster of sacks are gone, look at its arms/legs for the next fewtargets low enough for you to hit. That should get the tree down to about a quarter of its health. At this point, you'll see the final cluster of sacks at his back. Burn off the branches blocking these with Firebombs and destroy the sacks.
You'll get some items for beating this boss along with the Curse-rotted Greatwood trophy. Now it's time to head back through that door opposite of the boss arena, and if you've explored this area before, you would have found a guy warning you about entering the church. Head there and use the lift in the building to go down (or up if you want to meet a giant friend that gives you a Young White Branch). You can also roll off the lift when its about halfway down to reach another area. You'll find an ally here that warns you about the giant fire creature below. If you head down there and trigger the fight, your new friend will assist you. Defeat this monster and you'll a Fire Gem along with 5000 souls. Hopefully you do without letting your new friend die.
There is a treasure chest somewhere in the shack overlooking the battle area that houses some Human Pine Resin too. Take the lift down to the lowest level.
Defeat the mighty sword-wielding ice monster here. It doesn't have that much but does deal ton of damage, especially if the combos land. It's impossible to successfully block all of this enemy's attacks so employ a block and dodge tactic. Wait for the combos to complete before countering. You'll receive an Irithyll Straight Sword for beating him. Open the door to the Road of Sacrifices up ahead.