Old Hall House, now the Main Building at The Harborside Inn, has had a variety of uses since it was built in the 1700s. In 1845, it was a dry goods store known as Oak Hall. Later it became a boarding house, called Hall House, a name it still had in the early 1900s.
Chappaquiddick House was for many years the quarters of the Home Club, a genteel social club for men of status in the early 1900s, being the original home of the Edgartown Yacht Club. It was built by Thomas Jernegan in 1819. His wife was the daughter of Rev. Thaxter and her mother lived across the street. Capt. Alexander P. Fisher, master of the ship General Scott, owned it for awhile. It became the Chappaquiddick House when it was bought by John J. Jeremiah, a pioneer Chappy summer resident, who used it as a gathering place for residents of that island, waiting to be picked up by their own boats.
Capt. Tristram P. Ripley House was the show place of its day when built about 1850, the year the captain married Eliza M. Mayhew, “the beauty of her day.” He was master of such famous whalers as Champion, Charles W. Morgan, Young Phoenix and Mercury. Eliza went with him on several voyages. When he retired, the captain went into the wood and coal business with his neighbor, Capt. Alexander Fisher. In the 1900s, the house was converted to an inn, being run under several names, one being the Studley House, Capt. George H. Studley, innkeeper.
Capt. Thomas Milton House was built by Thomas M. Coffin in 1840 for Capt. Milton, retired sea captain, who had become a successful businessman here. Milton was born in England and, it is said, came here first as a cabin boy on a whaler. Another story has him coming first on the privateer Yankee during the War of 1812. Records show that he was born in 1808, aged 21 years, and on March 17 of that year married an Edgartown girl, Jane Hammett Pratt. At the time of his marriage he listed his residence as Salem, Massachusetts. He made several voyages to the East Indies as ship’s master for the famed Boston ship owner, William Gray. Later, he was master of a packet running between Boston and Philadelphia.
Captain Milton continued his interest in shipping, investing in the ownership of many types of vessels, including whalers. He held part ownership in such well-known vessels as the Hero, the Five Sisters, the whale ships York and Splendid. He was sole owner of the bark Milton, named presumably for himself.
He retired from the sea about 1837 and became a prosperous businessman in Edgartown, investing wisely in prime pieces of real estate, including a store on Main Street which he rented out as a dry-goods emporium. In 1840, he paid Thomas Coffin $900 to build this house, with the stipulation that the material was to be furnished and hauled to the site by himself.
Better known than the house is the Pagoda Tree, said to have been brought from the Orient in a pot by the captain on one of his East Indies voyages. It is said he planted it about 1833 on this lot that he had bought for his future home. The tree is called the Flame Tree in the Orient. Its horticulture name is Sophra Japonica.
Captain Milton died November 25, 1862 at the age of 54, after many years in failing health. His wife died only a few days before.