During the late 1800s, Broadway between 8th and 23rd Streets was known as Ladies Mile because of the many fashionable department stores located there. The original stores themselves are long gone, but their elaborate cast-iron building facades remain.

Theodore Roosevelt’s Birthplace National Historic Site (28 E. 20th St., near Broadway, 212/260-1616, 9 a.m.–5 p.m. Tues.–Sat., admission $3, children under 16 free) is a handsome four-story brownstone and an exact replica of Theodore Roosevelt’s birthplace. It was rebuilt by Roosevelt’s family and friends just after his death in 1919 and only a few years after the original building was torn down. The museum is filled with thousands of engrossing photographs and the world’s largest collection of Roosevelt memorabilia, including TR’s christening dress and his parents’ wedding clothes.

Where 5th Avenue and the Ladies Mile meet at 23rd Street is one of Manhattan’s most famous and idiosyncratic landmarks. The Flatiron Building, more formally known as the Fuller Building, was designed by Chicago architect Daniel H. Burnham in 1902. Its nickname comes from its narrow triangular shape, only six feet wide at the northern end. H. G. Wells once described it as a “prow…ploughing up through the traffic of Broadway and 5th Avenue in the late-afternoon light.”