Iron Town Diner

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.

Unconventionality at its finest is showcased at the Museum of Bad Art. Just like the name states, the museum is dedicated to the display and preservation of “art too bad to be ignored.” The MOBA is the only museum of its kind and holds a collection of nearly 600 pieces, and exhibits between 50 and 70 works at a time. See bad art in all forms, from paintings to sculpture, photography and more.