Generally, those who are interested in the history of the town will be drawn to the relics of the past which are in abundance here: the old houses and buildings. The architectural styles are varied: however, there are more 18th Century colonial and l9th Century federal buildings than you will find in many New England towns.

The tour draws attention to what is left of the old buildings on Main Street. It also focuses on sites of selected historic buildings which have been replaced. Some buildings which have an obviously early date are not included because we lack sufficient detail at this time.

There are at least four 17th Century "saltbox" houses in Old Saybrook. Distinguishing features are the large center chimney, the lean-to rear addition, five window and center door facade.

Since Saybrook was originally settled in the 17th Century, it is natural to see these survivors of its beginnings.

Many of the houses have shingle exteriors. Shingles for siding probably started with the Dutch on Long Island in the mid-17th Century. Wood siding such as shingles were American features because of the bounty of wood in the colonies and the excellence of wood as an insulator.

Rough dates for these houses are from the mid-1600's to the early 1700's.

There are three noticeable center chimney "Georgian" houses on Main Street. Examples are at the corner of Route 1 and Main Street, at the corner of Maple Avenue and Main Street and at the corner of Pennywise Lane and Main Street. There are others throughout the town. Generally, they were built after the "saltbox" and spanned the period of the English Kings named George.

Of more generous proportions than the "saltbox," these houses were built with the center chimney still acting as a central heating unit. The fireplaces in practically every room are part of the chimney. The facade has 9 windows and a center doorway. The exterior is covered with clapboards, the descendant of the medieval European weatherboards, but again providing protection from the harsh New England winters. These houses were built during the 18th and early l9th Century.

The three double chimney "Georgian" houses on Main Street are evidence of early prosperity in Old Saybrook. With the same nine-window facade, center doorway and clapboard exterior, the double chimney provided for a center hallway, a stairway with access to each second floor room and better air circulation. Also the center hall provided for more formality in the reception of guests and strangers. In general the double chimney house was larger and more comfortable for its 18th Century inhabitants than the center chimney type. These houses were built during the 18th and early l9th Century.

"Federal" houses abound in Old Saybrook. The birth of the nation and its government modeled on Greek Democracy created an interest in Greek temple architectural forms. Columns, fan lights, fireplaces, and corner cupboards were rendered classical by American carpenters. Many of the "Federal" houses moved the facade to the gable end of the house as shown in the picture. Corner pilasters became more evident and in many cases were added to earlier houses. Churches and public buildings became Greek temples. "Federal" and "Greek Revival" seem to be two phrases describing the same architectural movement in the United States. These houses in Old Saybrook date from shortly after the Revolutionary War to about 1850.

By the late 1840's, enthusiasm for all things Greek declined in the United States. In Old Saybrook, eclectic, a composite of styles in one house abounds. This is sometimes called Victorian for the age when Queen Victoria ruled England. Bay windows, vertical board exteriors and intricate carpentry were popular. These and other innovations manifested themselves in the porches, under the eaves, and in the roof peaks as shown in this house. A large number and variety of Victorian houses may be found in Old Saybrook. From the seashore eclectic of Fenwick to the mansard "modernizing" of a house on Main Street to the Gothic Revival of the Grace Episcopal parsonage the word is variety. Variety best describes the architecture of the Victorian age here. These styles date from about 1836 to 1900.

Come and enjoy your stroll.

2. Upper Cemetery.
This cemetery was laid out in 1787 by the proprietors of the town commons. In the 19th Century, the common area was an important meeting place for the townspeople.

3. Edward Stanford House - 15 North Main St.
C. 1815 shows unusually fine Greek Revival features. Doric pilaster are formed over the corner posts and dentil work is on the cornice and over the front door. There is a delicate fan window in the front pediment. The builder was a descendent of Zacharia Sanford, witness when Indian Sachem Uncas deeded the land to the town's early settlers.

4. Coulter House - Route 1 and Main St.
A 1853 map shows this building as the house of H. Kirkland. The estate was sold to James Coulter in 1864. All indications are that the building has been used as an inn since 1859.

5. Ambrose Whittlesey House - 14 Main Street
Built in 1799 by Capt. Ambrose Whittlesey, a sea captain. The Georgian proportions are typical of the center chimney and double chimney houses of the 18th Centuty. The Whittlesey family was responsible for founding the library and other town institutions. In 1919 the house came into the possession of Miss Grace Pratt; the last surviving member of the Ambrose Whittlesey family.

6. George W. Walker House - 33 Main Street
This house is an architectural puzzle. It has the general appearance of the early 19th century, but the proportions are not true for such an early date. There is a distinct possibility of two houses being joined, and it is difficult to tell which house is the original.

7. Burns and Young - 50 Main Street
Constructed in 1905 where the Burns and Young market was located. This was one of the major stops for the New London/New Haven Trolley.

8. Ingham House - 56 Main Street
An octagonal (8 sided) prefab building purchased and constructed c. 1890 from the Sears and Roebuck Catalogue. The only one of its kind in the area.

9. Azariah Mather House - 166 Main Street
From 1728 to 1928 the Azariah Mather house stood on this site. He was the forth minister of the Congregational Church; direct descend of Cotton and Increase Mather from the Massachusetts Bay Colony. Mather's tombstone is one of the most interesting in Cypress Cemetary. A motion picture theater was built on the site in 1937.

10. Dr. Elisha Ely House - 163 Main Street
This c. 1783 house is one of the few gambrel roof center chimney homes of the 18th century left in Old Saybrook. The entrance porch is a later addition, but the frame is probably close to the original. The center window on the second floor is an original 6 over 9. Dr Ely had a hospital for a "communicating the smallpox" inoculation in 1781.

11. Strokes' Bros. Building - 274 and 276 Main St.
c. 1900. Originally this brick building housed Strokes Brother's Store. They ran their business for 33 years, it was one of the original department stores of the area.

12. 286 Main St.
It is believed the building dates back to pre-revolutionary times because of the beautiful chestnut pegged beams. Originally it was a school with a blacksmith shop in the rear. During the early 1900's it was known as the Gilt Edge, had a gas pump, pool room, hamburger and soda shop. It was the only place from New Haven to New London open 24 hours daily.

13. Town Hall - 302 Main St.
The Old Saybrook Town Hall was built in 1905 and originally used as a theatre. The stage area can be seen on the third floor. In 1963 it was remodeled into the present Town Hall.

14. Main Street School - Main Street
The present school is built around the earlier building that was built in the late 1800's. The original section, the peak roofed section facing Main Street, was bricked up in 1936 when the two large wings were built around it

15. Gad Baldwin House - 223 Main St.
Built, c. 1888, the front of the house has Greek Revival features which are contradicted by the shingle wall exterior. The whole structure conforms to the revival of classical interest while conforming to pride in wood construction.

16. J. Shipman House - 322 Main Street
c. 1836 The proportions are Greek Revival, especially characteristic is the slope of the roof, which is more gradual than the earlier colonial architecture. Further evidence of the early 19th century is the square attic window and the porticos framing the front door. The front porch was a later addition.

17. Humphrey Pratt Tavern - 287 Main St.
This structure, c. 1785 remained in the same family until 1943. It was a stage stop on the run between New Haven and Boston and served as the first Post Office. Notable architectural features include the ballroom housed in the ell which has a spring floor to facilitate dancing and accommodates a graceful blending of the gambrel roofed ell with the double chimney of the main building.

18. Samuel H. Pratt House 334 Main St.
Though not as ornate as some houses of this 1874 era, the ornamental detail under the eaves, on the porch and the large windows help establish visual contact with nature; yet the house retains the hint of Greek Revival which was common to 19th century architecture.

19. James Ingraham House - 305 Main St.
This c. 1811 house appears to be a Georgian half house. The window proportions and placement and the slope of the roof are Georgian while the other half appears to be a classic through hall double chimney house.

20. Grace Episcopal Church . 338 Main St.
The present church was constructed in 1872 find is best described as English Country style. The arches and flying buttresses are examples of Gothic characteristics which lend the look of a miniature medieval cathedral.

21. Rectory For Grace Episcopal Church - 338 Main
The c. 1873 home is a copy of a house seen in England by Rev. Jesse Heald. The exterior details are unusual to this area and perhaps to this country. Most notable are the Gothic windows in the front dormer underneath on the second floor The front porch has unusual woodwork to adorn the rail and columns.

22. Gen. William Hart House - 348 Main St. (Old Saybrook Historical Society)
William Hart, Jr. built this home for his bride, Esther Buckingham, in 1767. Hart served in the Revolutionary War and reached the rank of General. Later he was a candidate for Governor of Connecticut. The house has typical twelve over twelve windows, center hallway and twin chimneys, unique that they are also corner chimneys. The interior has wide floor boards, old wainscoting, and paneling. The house has been restored to its original authenticity by the Old Saybrook Historical Society, which uses it as a headquarters and museum.

23. Congregational Church - 366 Main St.
This is the fourth church building of the Saybrook Congregation. The first two were at Saybrook Point and the third opposite. The present building was constructed in 1840 and the architecture reflects that of Greek Revival. The Columns, the fluted pilaster, the general proportions all are of classic style. The sides were built flat on the ground and then lifted by a team of 20 oxen and placed in deep troughs uprighting the entire side. It was one of the first prefab churches in the country.

24. Humphrey Pratt Tavern Store - Pennywise Lane at Main St.
A 19th Century construction date can be assumed by the twelve over twelve windows. Tradition says that Gen. Lafayette made a purchase at the store when it was at the corner of Old Boston Post Rd. and Main St. By 1874 the building was moved to its present location. The building is probably the most well known as the pharmacy owned by Miss Anne L. James, the first black woman pharmacist in Connecticut.

25. Deacon Timothy Pratt House - 325 Main St.
c. 1746. The center chimney, clapboards, and real gambrel roof all reflect its colonial origin. For many years this house was known as the Treadway Place.

26. P.L. Shephard House - 341 Main St.
The low ceilings and through hall arrangement inside the house as well as the geometric arrangement of the front windows indicate colonial architecture. The mansard roof and ornate eyebrow dormers indicate later alterations, probably about the time the structure was used as the Seabury Institute (1875).

27. John Shipman House - 404 Main St.
The architecture exclusive of the dormer remodeling indicates, c. 1687, construction. The Cheesebrough map shows a house in this area in 1755 and the name John Shipman.

28. Joseph Buckingham House - 412 Main St.
The owners believe it was built in the late 17th Century supported by the architectural style. It has the general proportions of a lean-to saltbox, but the windows are of an 18th Century colonial.

29. W.E. Clark House - 363 Main St.
This house was built between 1859 and 1874. The bay windows emphasize the utility of space. The overhang of the roof and the exposed rafters in the overhang are a decided trademark of the stick style construction of that period.

30. William J. Clark House - 369 Main St.
Built c. 1838, shows Greek revival characteristics in the arrangement of the windows, the slope of the roof and the placement of the front door. The shingles were a later addition. The sunrise attic window seems characteristic of homes along the Connecticut shoreline. This is the same house where the remains of Lady Fenwick were taken in 1870 after being exhumed at Saybrook Point to make room for the railroad.

31. Justin B. Holman House - 381 Main St.
An early deed shows this property on the 1874 map. Evidence shows the projecting rafters under the overhanging roof and in general the proportionately high wall to width indicates the high ceilings of the late 19th century.

32. Gregory W. Denison House - 385 Main St.
This house incorporates some of the essential features of the stick style characteristic of the late 19th century. The overhanging roof has some intricate carpentry work that blends the house with the landscape. Other features which were departures from earlier homes are the complex detail around the roof porch and vertical battens in the outside walls.

33. Samuel Hart House - 395 Main St.
Built c. 1773 by Samuel Hart, brother of Gen. William Hart, Elisha Hart and Amelia Hart Hotchkiss, all children of Rev. William Hart. The center chimney construction is typical of the colonial era. Some interior rooms have the original paneled walls.

34. S. Kirkland House - 425 Main Street
Built in the late 18th Century, the architectural features indicate a Georgian half house: The slope of the roof and the regularity of the windows are two such features. The front porch and chimney are later additions.

35. William B. Tully House - 488 Main St.
The aspect of this home shows what Vincent Scully described as "poignant American longing to recall its 18th Century past." The exception to that longing reflects in the regular arrangement of windows and door with its overhanging eaves. This is a characteristic of the stick style.

36. Samuel Eliot House - 500 Main St.
Built c. 1737 by Samuel Eliot. In the mid-18th Century it was occupied by Capt. Stowe. The next occupant was a prosperous trader who is said to have engaged in slave trade. Capt. Newell married to Stowe's daughter was killed by slaves in the Cape Verde Islands in 1819. This is a good example of double chimney colonial architecture.

37. The Millstones
The Millstones are the last relics of the windmill built by the early settlers under the direction of Lion Gardiner in 1636. It stood here for 175 years.

George Offerjost
Project Chairman