Spend some time hanging out in the country's oldest park. The 50-acre Boston Common is the anchor for the Emerald Necklace park system and is the starting place of the famous Freedom Trail. There are quite a few monuments throughout the park, and several outdoor events take place in the Common throughout the year.
Show off your pool playing skills at Flat Top Johnny's, one of Boston's favorite places to shoot pool. In addition to pool, Flat Top Johnny's features pinball machines, dart boards, and more. While you're there, toss back a few beers or order a tasty bite to eat from the extensive menu.
Step into the opulence of yesteryear and tour the Otis House Museum. The house is the last surviving mansion in what used to be Boston's most affluent neighborhood in the 18th century; the man who owned the home, Harrison Gray Otis, was a lawyer who served in Congress and was mayor of the city at one time. The Otis House is still decorated with furnishings that were the best of their time period, including fine furniture pieces and art work.
Hang out at one of the nation's oldest bars. The Warren Tavern has been serving beer since 1780 and was a favorite watering hole for historical figures like George Washington and Paul Revere. Now days, this nightlife venue doubles as a restaurant that serves up brunch, lunch, and dinner, including favorites like burgers, shepard’s pie, steak, and, of course, New England clam chowder.