There are several faction you meet during your Main Quest journey. The railroad is one of them and this guide will provide you detail on how to get the tail to the Railroad and their Essential Quest which will lead us to one of the Ending of Fallout 4.
The Road to Freedom is the first Essential quest of the Faction Railroad. You need to Follow the tail which will take you to Desdemona and then continue with them by gaining their loyalty.
Objective
Walkthrough
There are various ways to contact Railroad:
Starting with the Freedom's tail from the fountain near Boston Common which says "At Journey's End Follow Freedom's Lantern". You need to tail the red brick path which will keep the Signs that says 'A7','L4' at Massachusetts State House, 'A2' at Old Granary Burying Ground, 'O6' at Old State House then at Old Corner Bookstore with sign '3I' you will encounter few assorted enemies.
Again continue with the sign/mark tail from Faneuil Hall with '1R' to Paul Revere House with mark '8D', but make sure you are ready to take on the bunch of Raiders and Super Mutants in these areas. After Eliminating all the enemies walk inside the park and continue with the final tail of Freedom which ends at Old North Church with mark '1R'.
You will notice that you have reached your destination as the Church's door is painted with a lantern. Make your way inside the church and keep following the lantern which will take you to Freedom tail ring. Rearrange the Word Railroad and then Speak to Desdemona(Leader of Railroad) and agree to join the Faction and help them with their cause. Thus, the mission will come to an end and you have successfully joined the Railroad.
Now that you have decided to join Railroad and Fight for their cause you must complete the Faction's Essential Quest. Deacon will brief you with the Quest.
Objective
Walkthrough
After you decided with Desdemona to stay with Railroad, go ahead and speak to Deacon, he will send you to Lexington with the help of the Escape Tunnel. Here you need to unchain the door in order to reel back the same route. Once you reach Lexington, speak to Deacon where he will ask you to get some info on someone called 'Tourist'(Ricky Dalton).
Meet the guy and give him the Railroad's password. Later Dalton will provide you the information of the old base called the Switchboard which is ruled by the Synth enemies. Now you have two options to enter the Old base:
We prefer the Sewers as it is easy and quick to get to the Switchboard. Once you reach there Deacon will open the doors for you and help you with accessing the security door in order to grab the Carrington's Prototype. Now head back to the Old North Church and let Desdemona know about your mission progress. She will be happy and ask you to get a codename if you don't have any she will refer you as "The Wanderer". Thus ending the mission and several side quest will be unlocked for Railroad.
You have started working with Railroad and now it's time to stay Loyal to Fight against the Foes like The Institute and the Brotherhood of Steel. You need to get access to the Institute in order to Get the password for Code Defender.
Objective
Walkthrough
During the Main Quest 'The Molecular Level', Desdemona handovers you a holotape that can be used inside the Institute's terminal and contact Patriot. Now speak with Tinker Tom to get the Network Scanner and head inside the Institute, access a terminal, insert the tape and Read all the messages from Patriot.
Once you done with Patriot, head towards the Maintenance Room(Advanced Systems) and speak with Liam Binet. She will introduce you to Synth Z1-14, now get back and inform Desdemona about the same. She will send you to PAM who will advise on you with entering the C.I.T. security system(Defender). After you get inside the you come to know that Wilfred Bergman has the login info at Cambridge Polymer Labs, here go and have a word with Molly(a Robot).
Now you need to get inside the Lab C3, by accessing Lab C4 and then from C5 you can pass across the hole in the wall. From there Climb the ramp of Debris and drop down to the third floor or else you can directly try hack and access the Lab C3 expert Terminal and get the Bergman's terminal password. Get back to Desdemona to get the updated plans for the future.
Head back in the Institute to talk to Liam Benet and Z1-14 which will take 24 hours to respond. Once he does respond he will ask you to get some weapons for the volunteers who are ready to stand for the same. From here you need to head to the storage area and take the elevator down where some Synths are waiting to fight. Then return to Z1-14 and inform him about your success and then speak with Father to continue with the Institute Quest: Mankind Redefined and Mass Fusion.
After gaining Father's trust, Z1-14 will inform you with about the Brotherhood of Steel's upcoming plans. Get back to Church to speak with Desdemona and inform her about your success. Thus ending the Mission and Desdemona will provide you with Railway Rifle and Railway Spike ammo to get ready with the Next Essential Quest Precipice of War.