Samantha starts off her trip to historic Dutchess County on the "Walkway Over the Hudson," taking in dramatic views over the Hudson River and surrounding Hudson Valley. She then visits Essie's Restaurant owned by Executive Chef Brandon Walker, sampling some of his Caribbean/Southern dishes. Heading to McEnroe Organic Farm, Samantha learns how this revolutionary farm converted itself into one of New York's first fully organic farms and market. At Sandanona Shooting Resort, Samantha takes aim at shooting sporting clays, one of the fastest growing sports in the country. Samantha then visits one of her personal favorite tea shops, Harney & Sons in nearby Millerton, and talks with its master tea blender. Visiting Hyde Park, Samantha discusses the accomplishments of Eleanor Roosevelt with a National Park Ranger at Val-Kill, a National Historic Site, and only National Historic Site dedicated to a First Lady. Continuing on, Samantha visits the Barrett Art Center and talks with accomplished artist, Ransome, about his art influence and the importance of his work. Finishing off her trip she visits Innisfree Garden, one of the top 10 gardens in the world and takes in the beautiful views.