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Wine connoisseurs, get your tickets to Chef Daniel Bruce's Boston Wine Festival, one of the nation's longest-running wine events. This isn't your typical, two-day festival; the festival spans three and a half months and hosts a few events each week. The 23-year-old event features wine tastings, paired with signature dishes created by Chef Bruce. Throughout the history of the Boston Wine Festival, the menu has never been repeated.

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.

The Old State House is where The Declaration of Independence was born – the stand for American freedom began here. This important civic building was used as the first state house for the Commonwealth of Massachusetts after the American Revolution was won, and was later utilized as the home for a number of other services like city hall and post office. The Old State House has been a museum dedicated to early Boston and American history since 1881.

The Boston Harbor Islands offer some perfect destinations for boating and kayaking. Along with playing on the water, fishing, hiking, camping and swimming are popular for this park, too. There are dozens of recreational pathways and trails to explore throughout the islands.