Did you know that Brooklyn used to have a diagonal street that ran through downtown through Fulton and Pearl to Boerum Place and Livingstone Street? This is Red Hook Lane, a path that existed even before the first Dutch and British settlers in colonial New York. Red Hook Lane’s origin dates back to the Canarsie native American tribe, who used this road as a trail between East River and Jamaica.

After the settlers, Red Hook Lane turned out to be beneficial for both the British and Colonial Armies during the Revolutionary War and even more favorable to General George Washington in his defense of Brooklyn Heights in 1776. British General Admiral William Howe defeated Washington’s troops on the trail pushing back the colonists in the beginning of the War of Independence. However, Red Hook Lane would eventually be a strategic place for colonial troops. Forgotten NY spoke with local historian John Burkard who writes that colonial armies would “position themselves on Red Hook Lane and take potshots at incoming British soldiers.”

Into the mid-19th century and until present day, Red Hook Lane developed an identity crisis with the construction of new brownstones and eventually commercial real estate. Into the 20th century, the former trail became the southern tip of Pearl Street, coming in from the East River. Soon after the 1970s, the Red Hook Lane received its name back until Fulton Street was cut into two areas with the establishment of Cadman Plaza.

Robert Moses is known to have contributed to the vanishment of Red Hook Lane with his completion of Gowanus Expressway, which created a barrier between Carroll Gardens and Red Hook. If you look northeast at anywhere in Red Hook, you will see the canal on its way to the Brooklyn-Queens Expressway and Brooklyn-Battery Tunnel.

Today, Red Hook Lane is cut into pieces that can be found on several avenues and streets in Downtown Brooklyn. This historical account of this area depicts the transformation of New York’s unique streets from the pre-colonial age to modern times. Looking back at the few current diagonal streets in New York City, we see admiration for uniqueness. But the story of Red Hook Lane seems to be somewhat unfortunate given the commercial changes to one of the city’s most historic areas.

Read more about the New York’s old grid here.