Caroline Street (Key West)

At its southwesternmost point, Caroline Street begins on Whitehead Street at the Presidential Gates to the Truman Annex, the site of a former naval base that opened to the public in 1986. Caroline Street's terminus on Whitehead is two blocks away from the southern terminus of U.S. Route 1. Between Whitehead and Telegraph Lane just a few hundred feet to the northeast, Caroline is a quiet, shaded street, before its left (northern) side opens up to a strip of businesses and shops. The road reaches its first major junction at Duval Street, yielding a largely commercialized zone; The Bull and Whistle Bar and Fogarty's Restaurant and Flying Monkeys Bar are situated at this intersection. However, upon leaving Duval, Caroline Street returns almost immediately to a chiefly residential road. Homes along this stretch of Caroline are noted for their architectural significance, representing a late-19th century "conch style" that incorporates elements of several more prominent styles, including Victorian and Colonial. Although many of these houses were constructed quickly and cheaply, their builders employed the same techniques that were used at the time to craft boats, lending them resistance to extreme weather. The only interruption of this residential stretch is a minor junction with one-way Ann Street, which terminates at Caroline with little fanfare. Further northeast, Caroline intersects Simonton Street to a less commercial degree than Duval. Elizabeth serves as a sort of transition point for Caroline, which becomes lined with small shops as it meets Peacon Lane; Peacon is a one-way street that approaches from the south. As Caroline continues toward the northeast, it crosses William Street and offers an obscured view of the Gulf of Mexico side of the island and vessels at port. ==History and culture==

Caroline Street is situated along the northwestern side of the island, in a historic district known as Old Town Key West. Part of the district, roughly defined as the area between Caroline Street and Angela Streets (which run parallel about four blocks apart), harbors many old houses, some of which belonged to famous writers and other influential persons. Many of the houses in the area have been converted into inns; the Curry Mansion Inn at the corner of Caroline and Ann streets was originally built in 1855 for the Currys, a prominent local family. Caroline Street, along with Margaret, William, Thomas, and Emma streets, were named for siblings of John Whitehead, who—in 1819—became stranded on Key West after a shipwreck and took note of the island's strategic geography. Whitehead's brother, William, surveyed the city of Key West in 1829. The original map from William Whitehead's survey shows the northwestern corner of the island, bounded by present-day Angela Street, designated as "town plot". This plot was the only part of the island which had a grid-like pattern of streets: five running southwest to northeast, including the path of Caroline Street, at least a dozen oriented from southeast to northwest, and Front Street, which borders the extreme northwestern coast of the island. Therefore, Caroline was cleared by 1829 at the latest, making it among the oldest streets in either the city or the island of Key West. When it received its name, however, is unclear. Eventually, the street was excluded from the lot of the Truman Annex, and disconnected from the water at its northeastern terminus by the construction of the former City Electric Power Plant on new land. The dynamics of the project changed throughout its course; in early 2011, the city approved spending for specific updates to infrastructure along the corridor, including improved lighting and signs, a more extensive sidewalk system, and versatility with regard to bicycle and pedestrian traffic. As recently as February 2012, additional requests for improvements were lodged with $720,000 available for the project. ==In popular culture==

Early in his career, Jimmy Buffett co-wrote "Woman Goin' Crazy on Caroline Street" with Steve Goodman. Buffett released the song on his 1976 album, ''Havana Daydreamin'.'' == See also ==