Samantha takes to the Charles River joining the Boston University Women's Lightweight Rowing team and gets a taste of this celebrated sport. The Union Oyster House is considered America's oldest working restaurant. Here, Samantha learns the craft of shucking oysters with a master shucker, then speaks with owner Joseph Milano about the Union Oyster House's history and its legacy. Finding her roots, Samantha visits the New England Historic Genealogical Society to investigate her lineage and meets with the VP of Research, who has done advanced research into Samantha's family surprising history. Along the Freedom Trail, Samantha visits the Old South Meeting House and learns about the importance of the building and its American Revolutionary roots as the planning place for the Boston Tea Party. Continuing on the Freedom Trail, Samantha visits Boston's North End and meets its local "Mayor" Frank DePasquale, who shows her around the neighborhood, which includes a visit to an authentic Italian Salumeria where they see how mozzarella is made. Roxbury is the heart of Boston's African American community and is also home to Hispanic, Caribbean, and Asian families. Samantha joins tour guide, Collin Knight, on a tour through the neighborhood where they discuss Dr. Martin Luther King, Jr.'s connection to Boston, then visit Frugal Bookstore, the only African American owned bookstore in Boston. At the Blossom Bar at Sichuan Garden, Samantha joins renown mixologist Ran Duan and his parents, who talk about their family moving to America from China when Ran was 3 then giving up their opera singing aspirations to instead open a Chinese Restaurant and how Ran elevated the businesses with his unique twist on it.