Start by burning the Undead Bone Shard in the shrine’s bonfire to increase the potency of your Estus Flasks and turn in the Estus Shard to Andre the Blacksmith.
Hand over the umbral ash to the Shrine Handmaiden and make sure to purchase the Grave Key from her expanded inventory and then hand over Loretta’s Bone to Greirat, located to the left of Andre the Blacksmith.
Speak with Yoel, in the dead end past Greirat, to obtain the "Beckon" gesture and depending on the number of times you’ve died you may be able to use the "Draw Out True Strength" option for your first Dark Sigil.
WARNING: Obtaining 5 Dark Sigils by using Yoel’s "Draw Out True Strength" option is vital for obtaining one of the four endings.
Return to the Dilapidated Bridge bonfire and make your way across the dangerous graveyard to enter the building across the way, but be careful of the Peasant Hollows hiding just inside the buildings entrance.
Once inside, head up the stairs and turn around to jump across the gap and collect the Great Scythe . If you continue you’ll reach the boss arena, a large room filled with some peasants and flower, but ignore this for now and instead open the large double doors before returning to the bonfire.
Travel to the Undead Settlement bonfire and enter the building again to reach the courtyard with the burning tree, but this time head across the bridge.
Defeat the two Peasant Hollows and then head around the right side of the building. There are multiple Hollow Slaves on the rooftops across the way and some hidden around the corners, but these can be handled fairly easy with your bow due to their small health pool.
Collect the Fading Soul and check past the ladder for a Plank Shield before heading up the ladder for Homeward Bone x2 . Cross the rooftops to the left to find Firebomb x6 and then return up the ladder and drop off to the right.
There is a Hollow Manservant with a cage on his back that paces the area, but rather than kill him you’ll want to sneak up behind him and examine the cage.
This will teleport you to the Pit of Hollows, where Holy Knight Hodrick will hand over the Mound-makers covenant and a Homeward Bone . The altar behind Hodrick is where you can turn in the Vertebra Shackles for to the covenant, but you likely only have one at the moment.
You can now grab the Wargod Wooden Shield and return to the last bonfire with the Homeward Bone.
Return to the Hollow Manservant that teleported you to the Pit of Hollows and knock down the corpse at the back of the area for the Flame Stoneplate Ring , but don’t worry if it drops to the ground.
Head back to the bridge with the two Peasant Hollows, near the burning tree, and enter the barn to find some Peasant Hollows in the stalls to the right before grabbing the Large Soul of a Deserted Corpse .
The next building has a Hollow Slave hanging from the ceiling and outside is a Caduceus Round Shield that you can grab before crossing the bridge.
There are three firebomb tossing hollows on the top of the buildings who will become a nuisance as you check the area below, so use your bow to defeat them before moving forward.
There is a Soul of an Unknown Traveler on the torture device and collecting it will likely draw the attention of the Hollow Manservant with a large pot. Grab the Fire Clutch Ring on the wooden platform behind the torture device and then return to the bridge and drop to the ledge below with some more hollows and a Titanite Shard .
The ledge below leads to a bonfire and if you head out the other side of the building you can reach the roof with the three firefomb throwing hollows.
The cage behind the other side of the building has Cornyx of the Great Swamp , who will move to Firelink Shrine, and then collect the Hand Axe nearby.
As you backtrack toward the bonfire and head down the stairs, turn around and look toward the cage where Cornyx was to spot a corpse hanging from the rooftop that is holding a Partizan .
Drop off the other side of the rooftops, toward the Hollow Manservant, and take the stairs down until you reach the last set. Check around the back of the building to your left for a Large Soul of a Deserted Corpse and then quickly turn around to deal with the Hollow Slave that ambushes you from behind.
The large set of stairs with the Cathedral Evangelist leads to the boss arena again, but ignore it for now and head the opposite direction.
There are two Hollow Manservants across the bridge, which you’ll want to pull over individually, and then collect the Ember on the small bridge. Note the Hollow Manservant in the far corner overlooking the ledge, as it will try and perform a plunging attack on you later when you are below, and then head up the stairs nearby.
The lift ahead will rise as you approach and Siegward of Catarina will appear, confused as to why he can’t go up the lift. Go ahead and take the lift down, but be careful as you enter the next room since a dangerous Boreal Outrider Knight will stand guard in front of the doorway to Road of Sacrifices.
These enemies are rare, but are one-time spawns that offer some great fixed items when defeated. After obtaining the Irithyll Straight Sword by defeating the Boreal Knight, collect the Ember and exit the doors to activate the bonfire.
Enemy Info: Boreal Outrider Knights are savage enemies that do Frostbite with each of their attacks and should be taken very seriously. Keep your distance and use ranged combat, such as spells or arrows, or fight them at close range by taking a few strikes in between their sweeping attacks.
If you are having serious issues, strike them and then run so that they give up the chase and then catch them off guard as they return to their resting spot.