Start at Georgetown Cupcake, 3301 M Street NW, to beat the line that sometimes forms there for the gooey-sweet goodies. The stars of TLC’s DC Cupcakes TV show, sisters Katherine Kallinis Berman and Sophie Kallinis LaMontagne, founded it in 2008.

       Walk south on 33rd Street NW and turn right onto the brick and granite cobblestones of Cady’s Alley, where you’ll find food, furniture, and fashion boutiques in reinvented industrial buildings.

       Turn right on 34th Street NW and then left on M Street NW, Georgetown’s main drag, with oodles of restaurants, bars, and retail therapy in historic row homes and commercial buildings. Turn right past Georgetown University’s Car Barn building to climb the 75 Exorcist Steps. This steep outdoor staircase became famous in the 1973 horror flick The Exorcist when Father Karras tumbled down it. The Exorcist’s author and screenwriter is Georgetown alumnus William Peter Blatty.

       Follow the steps to 36th Street NW. Pass the Tombs restaurant and bar on the left, the Georgetown University hangout that inspired the movie St. Elmo’s Fire. Turn left on N Street NW and follow it across 37th Street NW to climb 48 stairs into Georgetown University, the nation’s oldest Catholic and Jesuit university. At the top, turn left into the Mark Lauinger Memorial Library. The granite-flecked concrete structure was designed in 1970 by John Carl Warnecke, who also designed President Kennedy’s grave at Arlington National Cemetery. The library’s vast collections, which are accessible to researchers, include the Russell J. Bowen Collection on Intelligence, Security and Covert Activities. CIA technical analyst Col. Russell J. Bowen donated most of this unparalleled collection in 1993. CIA directors William E. Colby and Richard Helms, who both lived in Georgetown, later donated papers. Exit the library and stay right on the diagonal brick sidewalk toward the O Street exit gate. On the left is Georgetown’s flagship building, Healy Hall. The massive granite building with a steeple-like clock tower was built in 1877.

       Walk east on O Street NW to 34th Street NW. On the northwest corner is the four-story brick house where then-Congressman John F. Kennedy lived with his sister, Eunice, from 1949 to 1951, says Paul Kelsey Williams’ book, The Historic Homes of J.F.K. Henry Addison also lived there. He was mayor of Georgetown before it became part of Washington, D.C. On the northeast corner is the rambling, two-story brick mansion that Under Armour sports clothing founder Kevin Plank bought in 2013, Washingtonian magazine says. In 1996, Plank started his Baltimore-based company a block away in his grandmother’s three-story town house. His “new” eight-bedroom house, with a 34-foot ballroom and a heated lap pool, was also home to longtime ambassador David K. E. Bruce, who once worked for the OSS, America’s first modern-day spy agency.

       Continue walking east on the cobblestone street with metal tracks from the defunct DC Transit streetcar system, which stopped running in 1962. On the right is the Bodisco House, famous as a federal period brick home and because Baron Alexandre de Bodisco, the 54-year-old Russian ambassador who owned it, married a 16-year-old, the Library of Congress says. Now it’s home to Secretary of State and former Democratic presidential candidate John Kerry and his Mozambique-born wife, Maria Teresa Thierstein Simões-Ferreira Heinz Kerry, heir to the ketchup fortune of her late husband, Republican Sen. Henry John Heinz III.

       Turn right on 33rd Street NW and right again on N Street NW for the Kennedys’ former home one door down on the right. They lived in this three-story brick home with green shutters with Caroline and little “John-John” right before moving into the White House. (JFK’s pal Ben Bradlee moved next door after working as press attaché for the American Embassy in Paris and then for Newsweek, says Gregg Herken’s 2014 book, The Georgetown Set.)

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