|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 and aligning each letter in order at the 12:00 position.|
|Speak to Desdemona.|
|Reward: 300 XP|
|Leads to: Tradecraft|
There are multiple places to acquire the quest, specifically in Diamond City and Goodneighbor, from holotapes lying around, from overhearing conversations such from two residents of Diamond City near Valentine Detective Agency, from talking to Diamond City Security inside Diamond City couple of times, 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.
- 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, 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 likes 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 by just going to the Old North Church first. The quest will act normally after you input the password and the rewards will be granted, however no completion mark will show up at the end and the Pip-boy will not show Road to Freedom in the discovered/completed quest lists.
- Prior to completing this quest, you can find Deacon disguised in various places throughout the wasteland. Examples of this include the Memory Den in Goodneighbor, as a guard in Diamond city, or as a caravan worker in Bunker Hill.
- Prior to completing this quest, Desdemora, Glory, and Deacon are not marked as essential nor protected, so one can fire at the three and kill them before they turn on the light. This will result in quest failure.
- When answering Desdemona's question whether the Sole Survivor is willing to risk his/her own life to save a synth positively, the male and female Sole Survivor will respond with different lines, with the male Sole Survivor mentioning the Oath of Enlistment he made when joining the army.
- When responding positively to Desdemona's question, and pointing out how synths are slaves, Valentine will love and like these selected dialogue options, respectively.
- If you try to leave when answering Desdemona's question, she will order the Railroad to kill you, making you the enemy of the Railroad.
- When Deacon vouches for you, he will reference various events throughout the game that the player has completed, including helping rebuild the Minutemen, joining the Brotherhood, killing Kellogg, or saving Stockton's "daughter" from the Compound. However, he will only do so if you tracked down the Railroad on your own initiative.
- If you encounter them 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.
- If Kellogg is dead but the mission is not turned in Deacon will not mention his death.
- If doing this quest in order to have the Railroad decode the Courser chip, and are planning on having another faction help you with building the relay, make sure you complete this quest first by speaking to Desdemona. Otherwise, this quest will fail if you progress on Inside Job or Outside the Wire by uploading the network data for the Minutemen or the Brotherhood of Steel.
- If you arrive at the site already having the courser chip, Desdemona will allow you right away into the 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.
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 either, so open the console, click on them and type <Template error> No command specified..
- Xbox One 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.[verification overdue]