Built around 1836, the J. Shipman House, on Main Street in Old Saybrook, has bold Greek Revival detailing and a later side bay window and enclosed side porch. The building now houses Old Saybrook Youth & Family Services.
The J. Shipman House (1836)
Humphrey Pratt Tavern (1785)
Built around 1785, the Humphrey Pratt Tavern in Old Saybrook was a stage stop between New York and Boston and housed Saybrook’s first post office. There is also an attached ell containing a ballroom. The Marquis de Lafayette stayed at the Tavern in 1824. Humphrey Pratt, who also built a house in 1785 for Saybrook’s minister, Frederick William Hotchkiss, was a brother of Deacon Timothy Pratt, whose house stands nearby, and the Tavern remained in the family until 1943. The building also had an adjacent general store, built in 1790, which was later moved down the street and is now the James Pharmacy and Soda Fountain.
The Ambrose Whittlesey House (1799)
Ambrose Whittlesey was a sea captain who built his house in 1799 on Main Street in Old Saybrook. The ell of the house is earlier, dating to around 1765. The Whittleseys were civil leaders in Old Saybrook and founded the town library. In 1919, the house was acquired Grace Pratt, last surviving member of Ambrose Whittlesey’s family. In 1977, the house’s current owners bought it to become a home furnishings store, which has since grown into a shopping complex called Saybrook Country Barn.
Some readers of this site may be aware of the Connecticut town history links page I created. Each town has a page with links to relevant websites and online books. I have recently been working on a similar page for Massachusetts. So far, it only has a few towns (mostly ones where I’ve taken pictures of buildings). Some of the towns, like Cambridge, Springfield, Salem, Lexington and Concord have many links. Unsurprisingly, Boston has a massive number of links and a huge collection of online books on many different topics, which I have made easier to navigate with a number of internal links, listed at the top of the page. Please check out both the Massachusetts and Connecticut town link pages!
Ingham Octagon House (1890)
Located on Main Street in Old Saybrook is an octagon-shaped house known as the Ingham House. It was a prefab building, said to have been purchased from the Sears and Roebuck Catalogue around 1890. The attribution to Sears and Roebuck is open to question, because a number of online sources indicate that the company only began offering kit houses in 1908, and apparently such homes were only available in the United States starting around 1906. So the origins of the house must be considered as still undetermined. The building, which is not a completely symmetrical octagon, has been extensively remodeled to become a dentist’s office.
William Hart House (1767)
Located next to the First Congregational Church in Old Saybrook is the 1767 house of General William Hart, which is now the headquarters of the Old Saybrook Historical Society. Hart was a merchant engaged in the West Indies trade with his brother, Joseph. During the Revolutionary War, he outfitted privateers and led the First Regiment of Connecticut Light Horse Militia to Danbury, when that town was raided by the Brittish under Brig. Gen. William Tryon in 1777.
Old Buckingham House (1671)
The owners of the Joseph Buckingham House, long known as the Old Buckingham House, located on Main Street in Old Saybrook, believe the house was built in the late seventeenth century. The plaque on the front has the date of 1671. It is a saltbox house with later additions. It was once the home of Rev. Thomas Buckingham, one of Yale’s original founders and trustees, and it is believed to be the site of the first Yale commencement in 1702.
The Deacon Timothy Pratt House (1746)
On Main Street in Old Saybrook is a bed & breakfast called the Deacon Timothy Pratt House. The house was built around 1746 for Timothy Pratt, Sr. and was later occupied by his son Timothy, born in 1748, who was a carpenter and a deacon in the Congregational Church. The house may have served as a private school in the 1790s. It was later known as the Treadway House.
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