Old Saybrook’s location on a point at the mile-wide mouth of the Connecticut River was arguably the most geographically desirable location in Colonial Connecticut. And its possession was a constant source of contention in its early days. the Dutch, who set up a trading post here in 1623 and the British, who followed a few years later, jockeyed for its ownership until a show of force by new governor John Winthrop in 1635 discouraged Dutch interests forever. And of course, the Indians who were living here were not anxious to leave, instigating the Pequot Wars. Even after Denmark surrendered New York to the English, Old Saybrook was the target of a take-over attempt by its British governor, Sir Edmund Andros.

Through it all, Old Saybrook emerged as the fourth oldest town in Connecticut and as the settlers spread out the towns of Lyme, Old Lyme, Westbrook, Chester, Essex and Deep River evolved form the mother town. Yale University was founded in Old Saybrook as the Collegiate School for the education of ministers in 1700.  The Saybrook College of Yale University Seal is used as the Town logo on its letterhead and town-owned vehicles.

Because of its location at the mouth of the river, Saybrook became an important center for coastal trade and for trans-shipment from river boats to ocean ships.  In the 1700’s and 1800’s along the shore of North Cove, and even extending out onto the river shore near the cove’s mouth, were built many warehouses and wharf’s to handle the ships and their cargoes. But otherwise industry never gained an enthusiastic foothold in town.

Instead the seaside location lured the tourist trade early on. The first resort development was recorded in 1870 when a company was formed to build cottages and hotels at Lynde’s Farm, known as Light House Point where it was said the temperature seldom rose above 84 degrees and “sea breezes blew from three points on the compass.” This development set a new standard for seaside resorts by restricting building specifications and prohibiting amusement concessions. One of the new breed of leisure class to seek out those sea breezes was Dr. Thomas Hepburn who brought his family to the Fenwick area of Old Saybrook in 1912. His daughter Katharine, was not yet five at the time.  

Our walking tour of Old Saybrook, up and down Main Street, won’t actually see the historic waters but won’t be so far away as to miss the salt air when the breezes are up...

Memorial Green
300 Block of Main Street

Memorial Green is a 2-acre square open space where Korean War and World War monuments are grouped. The gazebo that was donated by the Old Saybrook Rotary Club in 1975. Ornamental plantings have been placed throughout the green, giving it the appearance of a park.


Grace Episcopal Church  
336 Main Street

This is the second church for the Episcopal congregation on this site, constructed in the English Gothic style in 1871. The first church meetings began in 1825 and the cornerstone for the initial church was laid in 1830. When it was replaced it was moved, minus its spire, around the corner on the Boston Post Road. The Victorian rectory to the south was constructed in 1892; the white frame house to the north, the Chapman House, was acquired by Grace Church in 1972. 


William Hart House
350 Main Street

William Hart was equally adept on horseback and at the helm of a sailing ship. During the American Revolution he led the First Regiment of Connecticut Light Horse Militia to join a force of 500 militia and 100 Continentals to Danbury against a raid by deposed New York governor William Tryon. Hart and his brothers also armed their merchant ships in privateering forays against the British. Hart and his first wife, Ester Buckingham were noted in Colonial Connecticut for their lavish parties in this handsome Georgian house that dares to 1767. The small Greek Revival entrance came along in the mid-1800s. The house is now headquarters of the Old Saybrook Historical Society. Behind the house is a replicated carriage shed that contains the Frank Stevenson Archive.

First Church of Christ 
366 Main Street

This is the fourth meetinghouse for the congregation that was organized in 1646. The Greek Revival building features a square, two-stage tower that surmounts an impressive portico of fluted Doric columns. One of the windows from the previous meetinghouse that was built on the Church Green across the way in 1726, a casement leaded sash with imported English glass, is on exhibit in the treasure cabinets inside.

John Shipman House
404 Main Street

The core of this house stretches back into the 17th century; inside it still has four fireplaces and a beehive oven.  

Buckingham House
412 Main Street

This is another house with roots extending back into the 17th century, owned by the Buckingham family, perhaps as early as 1671. Thomas Buckingham was an early minister of First Church and in on the founding of the school that became Yale University. The sloping rear gives the Colonial house a saltbox appearance.


Timothy Pratt House
325 Main Street

Timothy Pratt built this house in 1746 where his son, Timothy Pratt, Jr. was born two years later. Paratt the younger became a carpenter and served as a deacon in First Church across the street. Before the 18th century was out, the building served as a co-educational school. Today the Pratt house is a bed-and-breakfast that retains many fine original details including original wide-board floors, hand-hewn beams, wainscoting, a corner cupboard, beehive oven and 12 working fireplaces.

James Gallery & Soda Fountain
2 Pennywise Lane

Built in 1790, the core of this building was the general store for the Humphrey Pratt Tavern. It is said that the Marquis de Lafayette stopped at the store in 1824 to make a purchase. Tradition maintains that French hero of the American Revolution left with either a pair of socks or a bar of saddle soap. 

The store was originally located adjacent to the tavern but was moved here in 1877 where it became a pharmacy. Peter Lane added the soda fountain in 1896. When he went to fight in World War I he left his sister-in-law, Anna Louise James in charge of the pharmacy. And so she would remain for the next 50 years, until 1967. Miss James was the first black woman to graduate from the Brooklyn College of Pharmacy and the first female African American pharmacist in the state of Connecticut.

Humphrey Pratt Tavern
287 Main Street

Built around 1785, the Humphrey Pratt Tavern was a well-known stage stop between New York and Boston. The town’s first post office was housed here. The gambrel-roofed ell extending to the back was featured a ballroom on the second floor. The building was only owned by two families for more than 200 years. 

St. John Church
161 Main Street 

The Norwich Diocese established a presence in Old Saybrook when the Catholics bought an abandoned skate factory and converted into a church. In 1884 the building was renovated and a steeple and organ loft added.


old advertising sign
276 Main Street  

America has a long history of painting advertising signs on buildings; barns in rural areas and brick walls in town. Here is a painted sign for a real estate broker that still endures.

The Katharine Hepburn Cultural Arts Center
300 Main Street

Old Saybrook’s most famous resident was Katharine Hepburn, born in Hartford to an heiress to the Corning Glass fortune and a urologist father. In 1911 Dr. Thomas Hepburn bought a summer home in Fenwick, Old Saybrook in 1911. In 1997, after retiring from the most honored career in American movie history, Katharine Hepburn moved from her New York City home to live in the family retreat full time. She died here in 2003 at the age of 96. Old Town Hall was constructed in 1908 in the Colonial Revival style as a performance house for the old Saybrook Musical and Dramatic Club. The Town Hall also screened the first movies in Old Saybrook as the center of the town’s entertainment for more than 40 years. In the 1950s the Town of Old Saybrook brought the theater to an end, dividing the audience chamber into town offices and turning the stage into a conference room. In 2003, with the town offices removed into more expansive quarters, the building was restored to its original use as a theater. Two years later, the Hepburn family approved the naming of the Katharine Hepburn Cultural Arts Center.  

Town Hall
302 Main Street

The Main Street School was built in the Colonial Revival style in 1936. It landed on the Connecticut Trust’s “Most Important Threatened Historic Places” in the early 2000s, just before money was appropriated to spruce up the brick building for the new Town Hall.