All teams travelled to the Old Burke School in search of their first clue for the leg. Everyone followed Boston natives Team Southie Boys except Team Air Force and Team Brown Family. Team Fogal Family called Team Geniuses, who misdirected them. Team Air Force arrived at the school first and discovered a sign reading "Look until you can see no more." In a classroom, they discovered a chalk board with Revolutionary War facts and decided to go to the location of the "shot heard 'round the world." All other teams except Team Fogal Family and Team Brown Family arrived at the school and discovered the sign. Josh Hanlon noticed light switches in the chalk board and flipped them. This caused the main lights to go out and black lights to come on, revealing two hidden messages. One read "Go to the Old Newgate Prison and search the darkness to find the way to the light." The other read "Go to the Wentworth House in Strawberry Banke and find what the Minutemen left behind." All teams present were instructed to pair off, with one team from each pair going to each destination. Messages hidden at each destination would when combined reveal the next destination. As the five teams were departing, Team Fogal Family again called Team Geniuses, who again misdirected them. Team Brown Family arrived at the school shortly thereafter and joined with the other five teams. Team Ex-CIA, Team Southie Boys and Team Wild Hanlons went to Wentworth House and Team Brown Family, Team Miss USA and Team Geniuses went to the prison. Team Wild Hanlons were partnered with Team Brown Family, but when the Browns called the Hanlons for a status update the Hanlons pretended they had bad cell reception, tried to mislead the Browns and finally hung up on them.