Caroline Street (Key West)
| Maintained by | City of Key West |
|---|---|
| Length | 0.5 mi (0.8 km) |
| West end | Whitehead Street in Key West |
| East end | Grinnell Street in Key West |
Caroline Street is an iconic and historically significant local road on the island of Key West, Florida. It extends approximately 0.5 miles (0.80 km) northeastward to Grinnell Street from Whitehead Street at its southwest end. One of the oldest roads on the island, Caroline Street is surrounded by many old houses, inns, and historic landmarks, which are known for their seclusion from the street by dense landscaping. From its mostly residential origins between Whitehead and Elizabeth streets, Caroline becomes more commercial, punctuated by numerous businesses. Situated within the historic "Old Town" district, Caroline Street was part of the original infrastructural layout of the island at the time of its 1829 mapping by William Whitehead. Other than changes to both its termini, the majority of its route has remained unaltered since then. Caroline Street was named for a sibling of Whitehead; his brother, John, became interested in the island after a shipwreck left him stranded in 1819. The street and some of its surrounding area have been subject to long-term improvement and beautification efforts, beginning chiefly in 1996.
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 is 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. Described as "stately", their lots are heavily landscaped, leaving several secluded.
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