Located at 1531 Southford Road in the village of Southford in Southbury, the Hurd-Osborn-Oatman House was built in 1806 by George Thompson as a hotel. As explained by John L. Rockey in the second volume of his History of New Haven County, Connecticut (1892):
In the period of time when the turnpike was the great thoroughfare between New Haven and Litchfield, Southford being 20 miles from the former place and 25 miles from the latter, hotels were here kept and were well patronized. [. . . ] The hotel known as the Oatman House for 35 years, was built by George Thompson in 1806, and first kept by him and then by his brother-in-law, Benjamin S. Hurd, followed by John Peck. Enos Foot was the landlord in 1845.
George Thompson and Benjamin Smith Hurd married two sisters, Clarissa and Esther, daughters of Adin Wheeler, who helped to fund construction of the hotel. The hotel had many owners over the years. Benjamin Blagg Osborn, son of merchant and Revolutionary War patriot Shadrach Osborn, was tavern-keeper in the 1820s. Charles R. Oatman (1827-1904), under whose name the hotel was long known, acquired the property in 1870. Oatman married Orinda T. Hurd, daughter of Benjamin R. Hurd, in 1850. The Oatman family owned the hotel until 1899 and even under later owners it was still known for many years as the C. R. Oatman Hotel. It later became the Fennbrock Dairy.
Travelers along the Old Post Road could once find accommodations at Josiah Fowler’s Tavern in Northford (current address 1710 Middletown Avenue). Fowler, who came to Northford in North Branford from Durham, built his tavern in 1776. The front entrance’s original five-pane colonial overlight survives as part of a later Federal doorway. Josiah Fowler‘s son, Maltby Fowler started Northford’s first industrial enterprise when he built a Button Shop in 1830.
Little is known about the origins of the house at 4 Southbury Road in Roxbury, which originally served as a tavern and stage-coah stop. It is said to have been built in 1785 by a man named Burwell. He may be identified with one of several men named Brothwell (a variant spelling of the same surname) who lived in Roxbury at the time [refer to Roxbury Place-Name Stories (2010) by Jeannine Green, p. 17 for more details]. In 1839 the building was purchased by the Thomas family who owned it for over a century. The most well known member of the family was Harvey Thomas (died 1894). He raised and sold horses. A nineteenth-century barn that survives on the property almost certainly served as his horse barn.
Located at 175 North Cove Road on Saybrook Point in Old Saybrook is a building erected around 1712 by John Burrows. Known as the Black Horse Tavern, it served travelers as an inn for many years and was a customs house during the brief period Saybrook was a port of entry on the Connecticut River. In the eighteenth and nineteenth centuries the area was a commercial district with a busy wharf. Ambrose Kirtland acquired the tavern in 1771 and deeded it to his son, Daniel Kirtland, in 1794. It may have been Daniel Kirtland who updated the building in the Federal style. From 1871 to 1924 the Valley Shore Railroad went right by the former tavern, which revived the tavern’s buiseness in the nineteenth century. The building was acquired by Henry Potter in 1866. He built a dock for trading vessels and a store on the site (since demolished) which he operated with his son until 1890, leaving it to his clerks, Robert Burns and Frank Young. In 1910 they moved the store, called Burns and Young, to Main Street in Old Saybrook. This marked the end of the North Cove neighborhood as a maritime commercial district. The house is now a private residence. The original Black Horse Tavern sign is now at the Connecticut Historical Society.
The oldest section of the building at 22 Knowles Road at Knowles Landing in Middle Haddam is possibly a house built on the site c. 1732-1735 by Jonathan Yeoman. For ten years (1735-1745), Yeoman ran a ferry across the Connecticut River. In 1747 the ferry licence was granted to Capt. Cornelius Knowles, for whom Knowles Landing is named. Jeremiah Taylor bought the Yeoman property in 1804, remodeling and expanding it in 1805 to serve as a tavern with a second-floor ballroom spanning the length of the building. The original one-and-a-half story, gambrel-roofed house became a two-and-a-half gable roofed structure. Taylor owned the building until 1826. The Italianate side veranda is a later addition. Jeremiah Taylor’s son, James Brainerd Taylor, was a minister during the Second Great Awakening whose life was a frequently used example of evangelical Protestant spirituality.
Located at the west end of the Willington Green is the Daniel Glazier Tavern. Built around 1815, the first recorded tavern keeper was Daniel’s son Isaac Glazier. The last tavern-keeper was Fielder Heath, who bought the property in 1839. The second-floor ballroom was used for town meetings in cold weather until 1840. The Tavern is thought to have been a station on the Underground Railroad. Charles T. Preston, a lawyer and Civil War veteran, bought the former tavern in 1881. His life is described in The Judicial and Civil History of Connecticut (1895):
Born in Willington, Conn., August 7, 1834. He was educated at the Connecticut Literary Institute at Suffield. He studied law with Hon. Richard Hubbard at Hartford, and was graduated at the Albany Law School. Admitted to the bar in Hartford county in March, 1858. He settled in practice in Hartford, serving during a portion of the war in the Twelfth Regiment of Conn. Volunteers. In 1867 he removed to Willington, where he is chiefly engaged in literary pursuits.
January 15, 1869, he married Mary E. Marsh, of New York city; she died May 2, 1871, and October 8, 1874, he married Carrie A. Preston.
At the northwest corner of the Boston Turnpike at 21 Bread & Milk Street in Coventry is a house built circa 1735 by John Wilson (1702-1773). After his death in 1773, the house passed to his son William (1729-1819), who married Sarah Rust, and his grandson Jacob (1749-1826), who married Hannah Dimmock in 1771. Jacob Wilson operated a tavern at the house from 1773 until 1817, when he sold the property to Joshua Frink.