In 1714, John Twitchell (c. 1699-1739) built a small one-story with attic dwelling at what is now 90 Oxford Road in Oxford. Around 1741 the Washband (or Washburn) family purchased the property and enlarged the house to serve as a tavern. In 1784, coinciding with the opening of the Oxford Turnpike, the family enlarged the building again, adding what amounted to a new house attached to the old one. The Washband family operated the tavern for several generations. Before the Civil War, the tavern was a stop on the Underground Railroad. Hiding places are said to exist in the cellar. The former tavern is now home to Daoud & Associates.
At the corner of Old Colony Road and Westford Road in Eastford (one of the buildings at 245 Old Colony Road near Eastford Green) is a former inn. The earliest part of the building is the rear ell, erected c. 1790-1800. The front section was built c. 1820–1835–1843. The building served as an inn, originally called the Eastford House. For a time, starting in the 1840s, the inn was called the Temperance House. In 1918 the property was acquired by Waldo and Beatrice Kennedy, who renamed it the General Lyon Inn in honor of Gen. Nathaniel Lyon, an Eastford native who was the first Union general killed during the Civil War. He died at the Battle of Wilson’s Creek in Missouri on August 10, 1861. Many of those who attended Gen. Lyon’s funeral in Eastford stayed at the inn. Beatrice E. Kennedy continued to operate the inn and restaurant until 1975. The Inn finally closed in 1979 and is now the Gen. Lyon Apartments.
The house at 439 Simsbury Road in Bloomfield was built in 1750 by a member of the Cadwell family. The site was once headquarters of the Hartford to Wesfield stage line. In 1830, the house was purchased by James Prosser, who remodeled it to become the Prosser Inn. James’ son, Levi Prosser, later lived in Massachusetts. In 1900 he left one sixth of his estate ($16,255.85) to the Town of Bloomfield to establish what is now the Prosser Public Library.
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.