Margaret Hamilton House – Witch’s House // 1852

Photo by Paul VanDerWerf

This house sits alone on Cape Island off the southern tip of Southport, Maine and has been known as the “Witch’s House” for decades. The island was purchased by actress Margaret Hamilton and her son, Hamilton “Ham” Meserve in 1961. The 20-acre island is about 900 feet from the mainland and includes this adapted farmhouse, originally built in 1852. Margaret Hamilton, best-known for her role as the Wicked Witch of the West in the 1939 movie, The Wizard of Oz, spent her summers in this house until her death in 1985. The island to this day is lovingly referred to as the Witch’s Island, a nod to a great actress and woman, Margaret Hamilton.

Southport General Store and Barn // 1895

In 1882, Edward Everett Pinkham, known as Everett, opened a new store in one side of his house on Hendrick Hill in the island community of Southport, Maine. The store was known for years as E. E. Pinkham and Son. Everett soon built a proper store adjacent to his house. He served the Town of Southport in many capacities: Postmaster, Town Clerk (1887-1905) Treasurer (1883), and Selectman (1888-1893). Sadly, on May 21, 1895, the store and house burned along with all of the old town records inside. The community helped Everett rebuild the present general store before the busy summer season. Edward’s son “Charlie”, would take over the business and the building has served as the town’s social center ever since. Year-round and summer residents bump into eachother at the store, catch up, and share local news, like every general store should be! Sadly, in so many communities, the “general store” has been replaced by big box retailers or convenience stores, removing the sense of community or place, so these businesses are more important than ever!

Southport United Methodist Church // 1904

The Southport United Methodist Church of Southport sits cross the street from the Town Hall of Southport, Maine, and is one of the best examples of a Shingle style church in the state. The modestly sized church was built in 1904, shortly after a fire destroyed the local Methodist congregation’s former church building. Members hired the great Maine architect, John Calvin Stevens, who had just joined in a professional partnership with his son, John Howard Stevens, to design the new church. It remains as one of the more notable architectural landmarks in the town of roughly 600 year-round residents.

Southport Congregational Church // 1875

Southport was and still is a part of Fairfield, Connecticut, but it has long been very different from the geographic center of town. Largely due to distance, Fairfield Congregationalists in the Southport area of town sought to establish a new parish to worship closer to home. By the 1840s, their request was granted and a small wood-frame Greek Revival house of worship was built in 1843. By 1871, the increase in population and wealth in the village necessitated a new, larger church. The congregation hired the architectural team of Lambert and Bunnell who made a huge statement here! It is constructed of granite ashlar masonry with a steeply pitched roof and soaring spires.

William W. Wakeman Mansion // c.1833

William Webb Wakeman was born in Southport, Connecticut on June 19, 1799, the son of Jesup Wakeman, an eminent citizen of the community. As a young man, William worked with his father in his commercial and trade enterprises. He acquired his own vessel early in his career, and gradually accumulated a line of trade vessels, sailing to New York, Savannah, Georgia and Galveston, Texas. By mid-century he was involved in the East Indian and China trade under the firm name of Wakeman, Dimon & Co. He built and owned a line of steamships during the late 50s, and was commissioned by the Federal government during the Civil War to transport troops and equipment. His massive Greek Revival mansion was built around 1833 on one of the largest house lots in the village, perched high on a hill overlooking the harbor. The three-bayed facade is framed by a two-story portico. Supported by four fluted columns, the capitals and entablature are similar to the “composed” order of Minard Lafever and the “composite” order of Asher Benjamin, popularized in the 1830s and 40s in their pattern books for architects and builders. After William died in 1869, it was likely his widow, Mary Catherine (who lived to be 99 years old, outliving all of her six children) who enlarged the home with massive two-story ells.

Trinity Parish Chapel, Southport // 1872

The Trinity Episcopal Church in the Southport section of Fairfield, Connecticut was established in 1725. As the parish and town grew, a large and architecturally stunning church was erected in 1862, and housed services for some of the wealthiest and well-connected residents of Connecticut. During Rev. Edward Wells’ rectorship, it was decided that a parish school was needed, and as an ardent believer in religious training, he started planning for a new chapel for use as a school. The Trinity Parish Chapel was designed by Southport architects Disbrow & Taylor and erected 1871-72. This Gothic Revival building is an excellent example of the rural church architecture which enjoyed widespread popularity throughout the country during the mid 19th century. Designed on a simple rectangular and decorative wooden bell cote, the small chapel’s board-and-batten siding and modest though strong Gothic details create a composition which compliments the more grand church just steps away. The chapel was originally built as a free-standing building, but was connected by a large, brick addition in the 20th century.

Chidsey-Dimon House // c.1850

Located on Harbor Road in Southport, CT, this stunning Italianate residence is properly sited on a small bluff overlooking the village’s harbor. According to historic maps, the house was owned by an “I. Chidsey” who appears to be Isaac Chidsey (1793-1865). The large Italianate style home is boxy in form and stands three full stories with two original one-story side wings. Sleeping porches were added in the early 20th century; those along with the rooftop belvedere, would allow for sweeping views of ships entering and exiting the harbor here. The house was recently restored by the architectural firm of Fairfax & Sammons and it looks amazing!

Oliver Perry House // 1843

This imposing Greek Revival house is located in Southport and is one of a handful of the stunning Classically designed mansions near the waterfront. The house was built in 1843 for Oliver Perry a Yale Law School graduate who did not work in law, but became a successful merchant and businessman instead. Oliver H. Perry established his fortune as a shipowner and a merchant and was Treasurer and Director of the Southport National Bank. He was active in civic affairs and served as speaker of the house of the Connecticut General Assembly and commissioner to survey and settle the border dispute between Connecticut and New York. His Southport house is a stunning example of the Greek Revival style in the temple form with a two-story projecting pedimented portico supported by four Doric columns.

Charles Gilman House // 1871

Southport, the coastal village in Fairfield, Connecticut is an old house lover’s dream! Case-in-point, the Charles Gilman House. Charles Gilman, a Bridgeport lawyer, constructed this house on the ridge parallel to Main Street in Southport between 1871-1874. The building is a fine example of the Stick style of architecture, in which the decoration on facades and gable ends reflects the building’s internal structure. Gilman used the services of two New York architects, J. Cleaveland Cady and William H. Beers, to design the house and the later (1900) library addition, respectively. In the 20th century, the house was owned by Richard Joyce Smith, an attorney who was hired to guide the New Haven Railroad through a long and tricky bankruptcy reorganization ending it it being acquired by the Penn Central in 1975.

Samuel Bradley House // 1715

Welcome to Southport, one of the most walkable and charming seaside villages in all of Connecticut, and it’s also in Fairfield! Southport became a leading coastal port on Long Island Sound, its ships carrying produce and goods back and forth to New York City. Sea captains houses, historic banks, and stunning churches line the streets in the village and are all in a great state of preservation. This is because much of the old village area is part of a local historic district, first established in 1967, where buildings from three centuries are protected for future generations. This house was built in East Haven, Connecticut by Samuel Bradley in 1715. The saltbox house is evocative of many early Colonial homes of Connecticut built at the time with a large central chimney and symmetrical facade. The house remained in the family until the mid-1940s when it was purchased, disassembled, shipped and reconstructed on this site on Harbor Road in Southport.

John Hoyt Perry House // c.1875

John Hoyt Perry was born in Southport in 1848, and graduated at Yale in 1870. He received his professional education at Columbia Law School and was admitted to the bar in Bridgeport, CT in 1872. He had an active law career in Connecticut, later working as a judge. He served Southport in the House of Representatives throughout much of the end of the 19th century. In 1913 he was elected to the Connecticut Senate and served as the minority leader. He served as counsel for the United States in arbitration proceedings with Chile in 1902, and as counsel for the town of Fairfield. This home in Southport was constructed for him, likely around 1875 after he accepted his position as a head attorney at a major firm nearby. The home can be classified as a blending of Stick style and Queen Anne Victorian design with the asymmetrical form, tower, large porch with projecting porte-cochere, shingle siding, and bargeboards.

Southport Savings Bank // 1865

The Southport Savings Bank obtained a charter from the Connecticut General Assembly in May 1854, and was organized on September 25 of that year. Original incorporators included Paschal Sheffield, Austin Perry, Wakeman B. Meeker, Charles Perry, Prancis D. Perry, E.D. Sherwood, John Meeker, Frederick Marquand, and Andrew Bulkley. A new building, located at the foot of Main Street, was constructed to be accessible to shipowners, shop keepers, the farmer patronage, and commercial traders. This bank building was occupied in 1865, eventually merging with Bridgeport People’s Savings Bank on July 1, 1955, becoming the Southport Branch of the People’s Savings Bank – Bridgeport. It ceased to be a bank in the 2010s and is now occupied by the Southport School.

Moses Bulkley House // 1861

Constructed in 1861, this Victorian Gothic mansion in Southport, Connecticut, stands out amongst the many Classically inspired homes nearby. Designed by Bridgeport architects Lambert & Bunnell for Moses Bulkley (1796-1868), the house is designed on a cruciform plan, synonymous with the Gothic style. Expansive pointed gables trimmed with a gingerbread bargeboards, pointed arched windows, ogee arches trimmed with jigsaw tracery on the verandah, and a tall square tower topped with a steeply-pitched pyramidal roof are all seen in this beauty. If only it had a historically appropriate paint scheme to really make those details pop!

Wakeman Memorial Building // 1913

The Wakeman Memorial Building in Fairfield, CT, is one of a few buildings erected in the Southport area during the early twentieth century. The boldly proportioned central portico is supported by square Tuscan columns with an Ionic fretwork entablature and denticulated cornice, and topped by a spindled parapet and an elliptical shaped Palladian window on the second story. The red tiled gambrel roof, splaying beyond the exterior walls, is bracketed by decorative modillions. The building was constructed in 1913 through funds by Miss Frances Wakeman in memory of her grandfather, Jesup Wakeman, at a cost of fifty thousand dollars. The building was used by the Boys and Girls Club of Southport as a club house, offering sewing classes, a reading room, and offices. The building was converted to a home after the Boys and Girls Club moved to a larger facility.

Charles Perry House // c.1830

Charles C. Perry (1795-1870) was a wealthy nineteenth-century shipowner and sea captain and a prominent figure within Southport’s community. After his father’s death in 1814, when Charles was just 25, he inherited a large sum of money from his father’s will and followed his footsteps as a career. Miah Perry’s will stipulated that in order to keep the family together, members were to reside at the family home for five years from his death if neither of the daughters married; “but in case they remain unmarried at the expiration of five years…my estate shall not be divided until eight years from my decease unless one of the said daughters should marry…partition may be immediately thereafter made.” Talk about pressure to get married!

It is unclear if any daughters got married before, (Julia, one daughter died in 1821 at 22 years old). That same year, Charles Perry seemingly got his part of the inheritance and acquired the land upon which this house stands. He was then twenty-six years old and unmarried. He appears to have built it later as a blending of the Federal and Greek Revival styles, perfectly complimenting each other.