Macy's Herald Square in the context of "34th Street (Manhattan)"

Pennsylvania Station (also known as New York Penn Station or simply Penn Station) is the main intercity railroad station in New York City and the busiest transportation facility in the Western Hemisphere, serving more than 600,000 passengers per weekday as of 2019. The station is located beneath Madison Square Garden in the block bounded by Seventh and Eighth Avenues and 31st and 33rd Streets and in the James A. Farley Building, with additional exits to nearby streets, in Midtown Manhattan. It is close to several popular Manhattan locations, including Herald Square, the Empire State Building, Koreatown, and Macy's Herald Square.

Penn Station has 21 tracks fed by seven tunnels, including its two North River Tunnels, four East River Tunnels, and one Empire Connection tunnel. It is at the center of the Northeast Corridor, a passenger rail line that connects New York City with Boston to its north and Philadelphia, Baltimore, and Washington, D.C. to its south, along with various intermediate stations. Intercity trains are operated by Amtrak, which owns the station, while commuter rail services are operated by the Long Island Rail Road (LIRR) and NJ Transit (NJT). Connections are available within the complex to the New York City Subway and buses.

Midtown South is a macro-neighborhood of the borough of Manhattan in New York City, generally characterized as constituting the southern portion of Midtown Manhattan. Midtown Manhattan hosts over 700,000 daily employees as a busy hub for workers, residents, and tourists. The Empire State Building, the Flatiron Building, Pennsylvania Station, Madison Square Garden, the Macy's Herald Square flagship store, Koreatown, and NYU Langone Medical Center are all located in Midtown South.

Madison Square Garden, colloquially known as the Garden or by its initials MSG, is a multi-purpose indoor arena in New York City. It is located in Midtown Manhattan between Seventh and Eighth avenues from 31st to 33rd streets above Pennsylvania Station. It is the fourth venue to bear the name “Madison Square Garden”; the first two, opened in 1879 and 1890, were located on Madison Square, on East 26th Street and Madison Avenue, with the third Madison Square Garden (1925) farther uptown at Eighth Avenue and 50th Street.

The Garden hosts professional ice hockey, professional basketball, boxing, mixed martial arts, concerts, ice shows, circuses, professional wrestling and other forms of sports and entertainment. It is close to other midtown Manhattan landmarks, including the Empire State Building, Koreatown and Macy's at Herald Square. It is home to the New York Rangers of the National Hockey League (NHL), the New York Knicks of the National Basketball Association (NBA) and was home to the New York Liberty of the Women's National Basketball Association (WNBA) from 1997 to 2017.

Macy's is an American department store chain founded in 1858 by Rowland Hussey Macy. The first store was located in Manhattan on Sixth Avenue between 13th and 14th Streets, south of the present-day flagship store at Herald Square on West 34th Street that opened in 1902. It expanded beyond the New York metropolitan area by acquisitions and conversions of regional department stores, facilitated by the purchase of Macy's by Federated Department Stores in 1994. It achieved a national footprint with the acquisition of The May Department Stores Company by Federated in 2005, which resulted in the conversion of its department stores to Macy's in 2006 and the renaming of Federated to Macy's, Inc. in 2007. Macy's is also a sister brand to the upmarket Bloomingdale's department store chain and Bluemercury beauty store chain.

Macy's is the largest department store company by retail sales in the United States, with 94,000 employees and an annual revenue of $25.3 billion as of 2023. It operates 450 locations in the country and its territories Puerto Rico and Guam as of 2025. Macy's Herald Square is one of the largest department stores in the world, spanning approximately 1.1 million square feet (100,000 m) of selling space and covering nearly an entire New York City block; its value is estimated at $3 billion. Macy's has conducted the annual Macy's Thanksgiving Day Parade in New York City since 1924 and has sponsored the city's annual Macy's 4th of July Fireworks since 1976.

The J. L. Hudson Company (commonly known simply as Hudson's) was an upscale retail department store chain based in Detroit, Michigan. Hudson's flagship store, on Woodward Avenue in Downtown Detroit (demolished October 24, 1998), was the tallest department store in the world in 1961, and, at one time, claimed to be the second-largest department store, after Macy's, in the United States, by square footage.