|Railroad main quest: Road to Freedom|
|(Optional) Acquire the quest in Goodneighbor or Diamond City.|
|Travel to Boston Common.|
Speak to the Tour Bot.
|Follow the red trail on the ground.|
Inspect the markers as you go along.
|Travel to the Old North Church.|
|Head to the basement.|
Find your way to the end where there is circular landmark on the wall.
|Spell RAILROAD by spinning the ring to align each letter in to the 12:00 position and pressing the button.|
|Speak to Desdemona.|
|Reward: 300 XP|
|Leads to: Tradecraft|
There are multiple places to acquire the quest, specifically in Diamond City and Goodneighbor, either from the Join the Railroad holotape that can be found lying around, overhearing between two residents of Diamond City near Valentine Detective Agency, talking to Diamond City security inside Diamond City, or from NPCs who mention the Railroad in the course of the main story, such as Piper and Amari. When the objective to 'Follow the Freedom Trail' is added, proceed to Boston Common to find the beginning of the trail. Talking to the tour bot will provide additional information but is ultimately unnecessary.
Follow the distinctive red trail of bricks in the ground from location to location. The red line on the ground is largely unbroken but there are a few stretches that are obscured by debris. In these places the trail is "improvised" using trails of red paint across the street or along wreckage of buses and walls. The trail will take you past several Bostonian landmarks and historical sites, each with a "Freedom Trail" seal outside in the sidewalk, with a letter circled and a number added in red paint. The first seal ("7A") is at Boston Common right near the tour bot. The second seal ("4L") is in front of the Massachusetts State House. The third seal ("2A") is at the entrance to the Old Granary burying ground. The fourth seal ("6O") is near the entrance to Goodneighbor (the Old State House from pre-War Boston's perspective). The fifth seal ("3I") is in front of the Old Corner Bookstore. The sixth seal ("5R") is at Faneuil Hall. The seventh seal ("8D") can be found in front of the Paul Revere house. The eighth and final seal ("1R") can be found at the Old North Church, the end of the trail.
- Alternatively, if players have already discovered it, they can simply travel to the Old North Church and skip the trail entirely.
Inside the Old North Church, kill a handful of ghouls and follow the lantern painting to find a way into the catacombs. At the end of the catacombs, there's another Freedom Trail marker with a ring that spins, similar in appearance to the eight seals on the trail. Rotate the outer wheel clockwise and counterpoise to align the letters with the arrow and press in the center to input the letter. Spell the word "RAILROAD" one letter at a time to open the secret door. If you make a mistake you must start spelling again from the beginning.
Once the door opens, go inside and the leader of the Railroad, Desdemona, shines a spotlight on you while two agents, Glory and Drummer Boy, train their guns on you. Speak however you want to them initially, it has no effect on your future relationship with them. Eventually Deacon will enter and list two of your major accomplishments in the Commonwealth, vouching for you. Desdemona will ask why you've come to the Railroad, if you know what a synth is, and most importantly, if you would risk your life to save them from their plight. Regardless of choices, the quest completes and Tradecraft starts immediately.
Companions react to three dialogues with Desdemona: When she asks why you have sought out the Railroad (only when selecting "Fight Institute," the other choices lead to no reactions and is not available if coming to the Railroad with the Courser chip); when she explains how the Institute treats synths ("as tools"); and ultimately, if you would risk your life to save a synth.
- Fighting the Institute
- Every companion, with the exception of Curie and Danse, like saying you want to make them pay for what they've done to your family ("Avenge my family"). Curie dislikes it, and Danse has no reaction.
- Nearly everyone will like saying you want to "protect others" from the same fate you've suffered. Curie loves this choice, while Cait, MacCready, and Strong have no reaction to it.
- Hancock and Curie love saying "Slavery is wrong." Preston and Strong like this choice.
- Most companions dislike saying "Synths are machines," while Danse and Strong like this choice. Cait and MacCready have no reaction.
- Codsworth has no reactions to either choice.
- "Would you risk your life for your fellow man? Even if that man is a synth?"
- Curie and Nick love saying you would. Most others like it, including Strong. Cait and MacCready dislike this choice, while Danse hates it.
- Even though Desdemona says there's "no shame in that," Nick, Piper, Preston, and Strong dislike you saying you wouldn't. Cait, Danse, and MacCready like this choice.
- Codsworth has no reactions to either choice.
- It is possible to complete the quest without picking it up in Diamond City or Goodneighbor by just going to the Old North Church first. The quest will act normally after inputting the password, albeit with alternative dialogue. Once the conversation ends, the quest will be skipped entirely and the reward will still be granted.
- Prior to completing this quest, one can find Deacon disguised in various places throughout the Commonwealth. Examples of this include the Memory Den in Goodneighbor, as a guard in Diamond City, or as a caravan worker in Bunker Hill.
- It is possible to kill any of the named Railroad members before they turn on the light. Doing this will result in quest failure and will flag the Sole Survivor as an enemy of the Railroad.
- When answering Desdemona's question whether the Sole Survivor is willing to risk their own life to save a synth positively, the Survivor will respond with different lines dependant on their gender, with the male Survivor mentioning the Oath of Enlistment he made when joining the United States Armed Forces before the Great War.
- When responding positively to Desdemona's question, and pointing out how synths are slaves, Valentine will love and like these selected dialogue options, respectively.
- Attempting to leave while answering Desdemona's question will cause her to order that the Railroad will kill the Sole Survivor, thus failing this quest and flagging the Sole Survivor as an enemy of the Railroad.
- When Deacon vouches for the Survivor, he will reference various events throughout the game that the player character has completed, including helping rebuild the Minutemen, joining the Brotherhood of Steel, clearing the Castle, clearing Fort Strong, killing Sinjin, killing Conrad Kellogg, helping Billy Peabody, helping Ironsides, being the champion of the Combat Zone, bailing out Nick Valentine from Vault 114, or saving Stockton's "daughter" from the Compound. However, he will only do so if the Survivor tracked down the Railroad on their own initiative.
- If Conrad Kellogg is dead, but if Reunions was not turned in, Deacon will not mention his death.
- If the Sole Survivor hasn't completed any event that can be cited by Deacon, Deacon will still vouch for the Survivor, saying that the Survivor is either smart or tough enough to have made it to the secret door, that the Railroad need friends more than ever, and that he has a really good feeling about the Survivor.
- If the Sole Survivor encounters the Railroad after having finished Hunter/Hunted, the entire conversation between Deacon and Desdemona will revolve around the Sole Survivor having killed a courser instead, without any reference to previous deeds whatsoever. In this case, Desdemona will allow the Sole Survivor right away into the Railroad HQ. However, she will then go back outside along with Deacon and the other agents and wait there to complete the conversation and give you the Tradecraft quest. This may be confusing as the player might expect to find them inside the HQ after having been allowed to enter.
- Starting the quest Institutionalized will fail this quest if not completed first.
Behind the scenes
The Freedom Trail, including the red (both painted and brick) paths, as well as the embedded seals, exists in the real world as well.
- PC In some cases, the game will freeze when attempting to enter certain buildings in Boston Common, including Old North Church, making this quest impossible to complete. The console command coc OldNorthChurch01 will teleport the player into Old North Church, past the entrance to the Railroad. The console command tcl must be used to go through and open the door to the Railroad properly. Exiting through the front entrance should work afterwards.[verified]
- PC When first approaching the Railroad HQ, Desdemona and the other guards may instantly become hostile, making the quest impossible to complete, and making you enemies with the Railroad. They become hostile right after unlocking the door, making it impossible to start a conversation even if you approach slowly or use a Stealth Boy.[verified]
- They are not susceptible to the Intimidation perk.
- PC After opening the door and entering, the conversation options will not be shown at all, and it is impossible to answer Desdemona's question or otherwise interact. In this case there is no option but to kill them all to gain access to Railroad HQ.[verified]