State Street is surely the smallest street in length compared against the other streets in this list (roughly half a mile), but its importance and historical meaning make up for it. As one of the main streets of Boston's Financial District, State Street sees financial business men and women tackle business matters every day. Numerous headquarters for various law firms, mutual fund companies, and banks are all squeezed onto this half-mile strip. At the end of State Street, you will come to the waterfront where ships sail to and from transporting people and items to various places. Business by day, at night and on weekends State Street turns into a hotbed of locals searching for fun nightlife at one of the many bars. Historically, State Street is home to the first Puritan settlers back in 1630 where they built houses all along the road.