The Barley Neck Inn had its beginnings in 1848, when Isaac and Mary Doane purchased the property which it now sits from Hannah Sparrow, widow of Josiah. Isaac Doane was one of four owners of the Cove Salt Works. By 1857, he and Mary had built a two room, two story Greek Revival house on their Barley Neck property. It extended to the pillar in the window seat of the current Doane Room. In 1868, Mary Doane, a widow at this time, sold the house to Captain Joseph Taylor, who had retired from the sea in 1866 as a partner in the Boston ship-owning firm of Seacomb and Taylor.

A 47 year-old Orleans native, born in 1821, who had attended Rock Harbor Academy and Andover, he was a pure Cape Codder, descended from the Taylor-Hopkins-Doane-Higgins families. Seacomb and Taylor commissioned the building of the clipper ship The Red Jacket, which in 1854 set a transatlantic record that would stand for twenty years, sailing from New York to Liverpool in 13 days, one hour and 25 minutes. It remains the record for a clipper ship.

It was Captain Taylor who built the south side of the current building, marked by the mansard roof. The Second Empire style of that and Taylor’s other additions reflects the strong French influence the pervaded Orleans from the time of its founding. The name of the town itself is French, and when Taylor was in residence, it was home to a population of French workers, constructing the telegraph there, that would operate between the U.S. and France.

At the Packet Landing on the other side of Barley Neck Road, on property still owned at the time by the Sparrow family, stood a gristmill, call the Old East Mill. The mill, which can be seen today at the Heritage Plantation in Sandwich, had been used originally to grind salt, and had been built of leftover timber when the Congregational Meeting House (now the Federated Church) rebuilt their porch in 1797. In 1819 it was moved to the hill overlooking Meeting House Pond to be near the grain producing areas of Barley Neck and Pochet. From the packet landing, produce was shipped by packet ship to Connecticut and New York.