Road to Freedom Road to Freedom is a Railroad main quest in " Fallout 4 " . Detailed walkthrough . 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 . 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 . Companion reactions . 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 . 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 .