The house at 404 Main Street in Old Saybrook has been dated back to 1697 or even 1687. By the mid-eighteenth century, the house was owned by John Shipman. This Cape-style house has been altered over the years, but still has four fireplaces and a beehive oven in the kitchen.
Located right next to Grace Episcopal Church in Old Saybrook is the Rectory, built in 1892, which replaced an earlier rectory, which had been lost in a fire. The design of the building was influenced by a house seen by the church’s rector in England. The Rectory is currently being leased out, with the rector and his wife live elsewhere.
For Easter, we’re featuring here an English Gothic-style church in Old Saybrook. Regular Episcopal services began to be held in Old Saybrook in 1825, meeting in the Center Schoolhouse. The first Grace Episcopal Church was constructed in 1830-1831, later replaced by the current church building, built in 1871-1872. The second church used the cornerstone of the first church, which was subsequently moved around the corner to the Old Boston Post Road.
Old Saybrook‘s Main Street School was built in 1936. In 1999, voters approved a referendum to convert it to serve as the new town hall. At the same time, restoration of the former town hall of 1911 was also approved and it has been restored as the Katharine Hepburn Cultural Arts Center.
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.
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.
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!