| Question | Answer | Letter |
| While he lived in DC, he was the coach that led the Boston Celtics to 9 NBA titles in the 1960s. | |
| This bar on Beacon Street was the inspiration for the TV show Cheers. | |
| The iconic neon advertising sign visible over the Green Monster in Fenway Park advertizes this oil company. | |
| This location in Boston Harbor was the site of a prison from 1896 to 1991, and is now home to the city's largest wastewater treatment plant. | |
| This chain of small parks around the city, including Boston Common, Arnold Arboretum and the Public Gardens, was designed by Frederick Law Olmstead. | |
| Boston's only zoo is located in and named for this 527 acre area. | |
| The costliest art heist in American history took place at this museum on The Fenway, a palazzo-style building that was home to its namesake, who also donated her collection. | |
| This Chief Justice of the Supreme Court was born and practiced law in Boston, and is best known for writing the 'clear and present danger' majority opinion in Schenck v US. | |
| The North End neighborhood is traditionally home to people who came from (or whose forebears came from) this country. | |
| This neighborhood shares a name with what was once called the Great Pond. It is home to the Forest Hills MBTA stop and the Boston Beer Company, makers of Sam Adams. | |
| Commonwealth Avenue, Beacon Street and Brookline Avenue all cross at this location, which also gives its name to the MBTA Green Line stop located below it. | |
| Boston's airport is named for this general who served in the Spanish-American War. | |
| He is the first Italian-American to serve as mayor of Boston, and the city's only five-time mayor. | |
| | Question | Answer | Letter |
| This Hockey Hall of Famer has had his number 8 retired by the Bruins. He is (unofficially) the last NHL player to score 50 goals in 50 games. | |
| The Central Artery tunnel that runs under downtown Boston is named for this former Speaker of the US House of Representatives, whose district included much of Boston. | |
| This historic downtown hotel, now owned by the Omni group, is known for creating the Boston cream pie and a namesake roll. Ho Chi Minh was a baker there in the 1910s. | |
| This popular dining and shopping location behind Faneiul Hall is named for the Boston mayor who oversaw its construction in the 1820s. | |
| This NFL franchise played in Boston from 1932 to 1936, after which owner George Marshall chose to move the team to its present location. | |
| These pedal-powered vehicles give cruises on the small lake in the Public Garden. | |
| This major street gets its name from the three hills that used to define Boston's geography. | |
| This downtown eatery is the oldest restaurant in the United States | |
| This scenic road named to honor those who fought abroad starts by the Arnold Arboretum and runs through Roslindale and West Roxbury before entering Dedham. | |
| Citi is now the lead name sponsor of this historic theater, formerly named for this computer magnate of the 1970s and '80s. | |
| This civil rights figure spent seven years in prison while living in Boston, during which time he learned of and embraced the Nation of Islam. | |
| This street that runs alongside Fenway Park is closed to traffic on game days to provide an outside entertainment area. | |
| The new cable-stayed bridge that carries Routes 93 and 1 is named for Bunker Hill and for this religious and civil rights leader who died of cancer in 1999. | |
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