Hilltop Colony, Virginia is a town that Paul Monroe acts as an ambassador for. The town is first mentioned in Issue 92 of The Walking Dead. Paul claims it is a farming community of 200 residents, led by a man named Gregory. The town is 20 miles from the Alexandria Safe-Zone. According to Paul, the town has no active weapons, which is why it has a trading network with two other communities. Paul says the town wants a trading network with the Alexandria Safe-Zone also. In Issue 94, Paul leads some of the survivors to the town.
Paul Monroe brings Rick Grimes and a group of survivors to the community for help, he and Gregory explain that they are under the control of The Saviors and their leader Negan, he goes on to say that they are forced to pay tribute to The Saviors, or they will be wiped out. However before Paul can finish, Ethan, a resident of Hilltop, comes back and informs the people that Negan has killed his group as they did not bring enough supplies. He then says that The Saviors asked him to deliver a message, which was to stab Gregory in order to kill him. After he stabs Gregory, Rick takes the opportunity to tackle Ethan and begin brawling with him, Rick uses Ethan's knife and cuts his throat open, killing him.
This stuns to residents and they begin to yell at Rick for his actions, Paul steps in and says that what Rick did was right and that Ethan was a coward. After escorting Rick and his group back inside the Hilltop's mansion, he returns to explaining that he called Rick here to ask for his help against The Saviors and that if Rick does rid them of the group, Hilltop will give Alexandria half their supplies. Rick accepts this deal and leaves, eager to deal with The Saviors.
After Negan executes Glenn, a furious Rick returns to the Hilltop and punches Gregory in the face, accusing him of not telling him and his group more about The Saviors. Gregory states that the Hilltop knew virtually nothing about The Saviors and that they did not even know Negan was a real person.
Sick of living with Rick, Maggie and Sophia move to the Hilltop for a chance at a better life. Maggie quickly bonds with Brianna. They have many conversations about their life in and before the apocalypse, they both agree that Gregory is a creep and make very crude comments about him.
Paul and Rick with the help of Ezekiel, devise a plan by using people from all three of their communities to fight off The Saviors. Much to the leader of Hilltop Gregory's displeasure of the idea Paul still goes through with it.
Sometime after The Savior hold up of the Alexandria Safe-Zone, The Saviors pay a visit to the Hilltop Colony and captures Gregory for use as a bargaining chip against the allied forces of Alexandria, the Hilltop and The Kingdom. Gregory cowardly sides with The Saviors, threatening to banish everyone who believes otherwise. When he and the Hilltop soldiers arrive back, they are met by Maggie Greene, who angrily punches him in the face after hearing that "Negan is quite reasonable", she then proceeds to make a speech about the war, and how Rick wants to make everything better for them, and begs them to join the cause.
Later, it is revealed the majority of the survivors agreed to fight, most of them leaving the colony to Alexandria, where they repel a Savior attack. As of now, Maggie Greene is the de facto leader of Hilltop. In Issue 121, Rick decides to move all the Alexandrians to the Hilltop.
The Hilltop is the biggest known survivor community of The Walking Dead universe, containing over 200 survivors.
This number increases significantly in Issue 121, in which Rick Grimes makes the decision to move himself, his family, and all the residents of the Alexandria Safe-Zone to the Hilltop Colony. Also, Ezekiel moves the residents from The Kingdom to the very same place.
Hilltop has had the least shown casualties in the All Out War storyarc.