Haddam Gaol and Workhouse (1845)

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When Middlesex County was formed in 1785, the county seat was to be shared by Middletown and Haddam. As a “half-shire” town, Haddam was required to built a courthouse and jail. The first jail, constructed of wood, was built in 1786, followed by a brick structure in 1812. This was replaced by the gable-roofed section of the later Gaol (Jail) and County Workhouse, constructed in 1844-1845 with stone from the Arnold granite quarry in Shailerville. The workhouse and barn were added in 1855. The Mansard-roofed section, which more than doubled the size of the building, was added in 1874. The jail continued to hold prisoners until 1969 and the following year became the Correctional Academy for the state, since 1972 known as the Connecticut Justice Academy.

Jared Pratt House (1803)

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Jared Pratt built a house on Main Street in Essex around 1803, after his marriage to Polly Bull. In 1854, Captain Isaiah Pratt purchased the home from his father, although his parents were allowed life use. Isaiah, who later altered the house in the Second Empire style, sold it to his sister, Mary Pratt, in 1868. In 1922, the main section of the building was moved from Main Street to what is now called Pratt Street to make room for the construction of a new town office building (now the Post Office).

New London Ledge Lighthouse (1909)

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The New London Ledge Lighthouse was built in 1909, on the Southwest Ledge at the mouth of the Thames River in New London Harbor. It was built after much lobbying to construct a new lighthouse, as the New London Harbor Light was deemed insufficient to direct ships around the dangerous ledges at the entrance to the harbor. The red brick New London Ledge Light is to have been built in the French Second Empire style at to the request of wealthy homeowners on the nearby shore, who wanted the new lighthouse to match the elegance of their own residences. The Coast Guard took over manning the lighthouse in 1939 and it was automated in 1987. New London Ledge Light is also famous as a haunted lighthouse (There are YouTube Videos here and here).

Goodspeed Opera House (1876)

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The Goodspeed Opera House is a notable historic landmark along the Connecticut River in East Haddam. It was built in 1876 by William Goodspeed, a merchant and banker. Originally serving as a store, office and steamship docking point, as well as having a theater on its top two floors, the Goodspeed was built in the distinctive Second Empire style (with a mansard roof) to attract the attention of traffic along the river. The first performance at the Opera House was on October 24, 1877. After Goodspeed’s death in 1926, the building was used for various purposes, including being a World War I militia base, a general store and a storage facility for the Highway Department. Having fallen into disrepair, it was restored in 1959 by Goodspeed Musicals, a non-profit organization dedicated to musical theater. Rededicated in 1963, the Goodspeed Opera House has continued since then to be the home for performances of musicals and is one of several facilities currently owned by Goodspeed Musicals.