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About the Apollo Theater: Harlem's acclaimed Apollo Theater is important not only because it honors and promotes the contributions of black performers but also because it is a living example of progress: the building was originally a burlesque theater that did not allow black patrons or performers. The theater shut down in 1933 after future New York City mayor Fiorello La Guardia launched an anti-burlesque campaign. Reopened under new management in 1934, the Apollo began to direct programming toward Harlem's burgeoning African-American community. That same year, Ella Fitzgerald made her singing debut and won one of the first Amateur Night contests. The spot earned landmark status in 1983 and—with its plush red curtains, stellar sight lines and oft-shouted mantra/TV spinoff, "It's Showtime at the Apollo!"—has become one of the most beloved and respected music halls in the United States.

While you're in the neighborhood: Legendary Harlem eateries and music clubs are within walking distance of the neighborhood's biggest symbol, the Apollo Theater. Sarah Vaughan and Duke Ellington have graced the stage at Showmans Jazz Club; jazz and blues veterans like Jerry Weldon and Lonnie Youngblood are frequent performers there these days. Billie's Black, a soul food joint, has an intimate bar, cozy tables and live music—ideal for date night. Sylvia's offers plates like Carolina-style catfish and waffles with fried chicken (a Harlem staple); finish with the banana pudding. Amy Ruth's, another local favorite, serves up comfort food for breakfast, lunch and dinner. Menu items include chicken and dumplings, baked macaroni and cheese, and waffles with chicken, steak, bacon or pork sausage. Or taste chef Marcus Samuelsson's interpretation of some of the neighborhood flavors mentioned above at his latest venture (and legend-in-the-making), Red Rooster. Meanwhile, Chez Lucienne is ideal for those hungry for French classics like escargots and boeuf bourguignon. Mediterranean- and Italian-food lovers should head to Ristorante Settepani for house-made pastas, such as ravioli, linguine, rigatoni and lasagna.

A short walk south are a few worthy places for an after-dinner (or show) drink. For an impressive brew list that lives up to the name, Bier International is a stellar pick. And anyone in the mood for a killer cocktail should stop at 67 Orange Street. Its name—and speakeasy ambience—harks back to Almack's Dance Hall, which occupied said address (Orange Street is today's Baxter Street). Almack's was opened in the 1840s by Pete Williams, one of the first black bar owners in NYC.