As Broadway marches north and west across Manhattan it forms a series of squares beginning with Union Square at 14th Street. The Union Square neighborhood is a thriving cultural, business, educational and health care hub. Throughout Manhattan and beyond, the vibrant community is known as the Heart of Off-Broadway and is celebrated for its top-notch restaurants, diverse retailers, excellent universities and hospitals, and one of the city’s most popular parks.

In this neighborhood are some of the city's trendiest restaurants lining Park Avenue South up to 23rd Street. Madison Square, the site of the original Madison Square Garden, is dominated by the Metropolitan Life Insurance Tower and the Flatiron Building (20-stories and triangular). To its east is Gramercy Park, a small, fenced park acessible only to residents of its surrounding townhouses. Theodore Roosevelt was born in this neighborhood.