Cummings-Abbott House // c.1735

Samuel Cummings (1709-1772) married Prudence Lawrence (1715-1796) and moved to Hollis, NH from Groton, MA. The couple had a home built in town and raised at least four children, Samuel Jr., Mary, Sibbel, and Prudence. The original house built by Cummings was a single-story, four room, center chimney type. After his death in 1772, the property passed to Cummings’ son, Samuel Cummings, Jr., an acknowledged Tory. Interestingly, Samuel’s sister Prudence was an ardent patriot, who moved to Pepperell, MA and married a militia man, David Wright. While the Revolutionary War was raging, Prudence visited her brother in the old family home, when she overheard her brother Samuel talk to his friend, a British army officer about passing information to the British. Prudence returned to Pepperell and gathered the women of the town. Then a 35-year-old mother of five, she organized 30 or 40 of them into a militia called ‘Mrs. David Wright’s Guard.’ The women dressed in their husbands’ clothes and carried whatever they could for weapons. As the men had probably taken muskets with them, the women probably used farm implements such as pitchforks. The women patrolled the roads leading into town. The group eventually captured two British soldiers on horseback and let them go only once they agreed to never come back to the colony. Due to this event, Prudence never spoke to her loyalist brother again.

In the 1850s, the house was owned by Superintendent of Schools, Levi Abbott and his wife, Matilda. It was the Abbotts who reportedly added a second story to the house with a hip roof, cornice and corner pilasters, giving it the appearance we see today.

William Bulkley House // 1767

The William Bulkley house was built circa 1767 and is one of the few extant pre-Revolution houses in Southport. In 1779, during the Revolutionary War, Fairfield and vicinity were burned and ravaged by Tory Loyalists. Only eleven houses throughout the region survived the burning; one of four in Southport was the Bulkley residence.

Osborn House // 1772

This homestead in Fairfield, Connecticut is situated on the edge of what was formerly called Pequot Swamp, and was originally built by Stephen Osborn in 1772. It is said to be the third Colonial dwelling erected in this part of the town and was left undisturbed by the British when they burned Fairfield in 1779 and raided various sections of the country along the shore. The home was originally located a few blocks away, but was moved in the 1950s when the highway (I-95) was routed through this part of Fairfield. The saltbox Georgian home was documented prior to the move by the Historic American Buildings Survey (HABS).

David Ogden House // c.1750

This saltbox house was built by 1750 for David Ogden at the time of his marriage to Jane Sturges. For the next 125 years it was home for the Ogden family in the farming and coastal shipping town of Fairfield. The home was sold out of the family in 1839 to Henry W. Banks, who continued to farm on the nearly 75 acres of farmland. By the 1920s, the home was suffering from deferred maintenance and was at risk of demolition. Luckily, Annie Burr Jennings (1855-1939), a philanthropist who was born into a wealthy family, sought to give back to her town. Jennings was instrumental in establishing and supporting a number of important community institutions, including the Fairfield Historical Society (now the Fairfield Museum) and the Fairfield Public Library. In 1931, she purchased the old Ogden Farmhouse from absentee owners and helped fund its restoration. The early saltbox vernacular Georgian home today is maintained by the Fairfield Museum and the Greenfield Hill Village Improvement Society.

Captain John Maltbie House // 1766

On July 7-8, 1779, the Red Coats marched through Fairfield torching houses to punish the locals for seeking independence. They killed locals, destroying anything they could find on their way out, setting fires to homes and civic buildings around the Green. This home was built by Isaac Tucker, later sold to Jonathan Maltbie, sea captain involved with East Indies trade. He later would fight against the British during the Revolution, and after the war, was hired as captain on one of the first cutter ships built, the Argus. During the British invasion of Fairfield, they attempted to set fire to this home three times, but it seemed to never go up in flames when they returned. The tradition holds that an elderly servant, hiding upstairs, put out the flames and saved the house from destruction, after the British Troops torched it. Burn marks apparently remain inside to this day. Since the home was built, the front door facing the street was relocated to the side, and a large multi-pane bay window was installed in its place.

Old Fairfield County Courthouse // 1794

Located at the Fairfield Town Green, the Georgian-style Fairfield County Courthouse stands as a reminder on the town of Fairfield’s Colonial-era history. The first courthouse at the site was built in 1720. After a fire destroyed the first (which housed the jail as well), a second structure was built in 1767. That second courthouse was the center of a thriving, wealthy village with a port just blocks away. In July 1779, the British landed in Fairfield and destroyed much of the town, harming its prosperity for decades to come (though it has clearly recovered since). In 1794, a new courthouse was built, also housing town offices. In 1870, it became solely a town hall (the County Court moved to Bridgeport years before) modified and altered in the Second Empire style to ‘modernize’ the building. As Colonial Revival resurged in popularity in the late 19th and early 20th- centuries, the town sought to bring back the Georgian style Town Hall building, in 1936 hiring architect Cameron Clark, to restore the building.

Sleepy Hollow Farm // c.1780

Without question, this property is the most photographed site in the tiny town of Pomfret, Vermont, if not the state. The property dates to the late 18th century when John and Samuel Doten moved to the newly settled town of Pomfret Vermont, overlooking the growing town of Woodstock in the valley below. The two brothers acquired vast farmland on the hills of Pomfret and each built farmhouses adjacent to eachother, with Samuel getting elevated land and John developing the land sunken off what is now known as Cloudland Road into this stunning property. Sleepy Hollow Farm remained in the Doten family for centuries until the 1950s, when the owners sold the property to move to Woodstock and work for Laurance Rockefeller, the famous philanthropist and conservationist, who later donated his Summer home in Woodstock to the National Park Service. The property sold numerous times in the late 20th century, and is presently owned by Aerosmith guitarist Joe Perry and his wife, Billie. They are clearly great stewards to the property’s rich history and various outbuildings, and must not care too much to have swarms of photographers at the end of their driveway year-round!

Brethren’s East Shop // 1819

This 1819 building was originally located next to the first dwelling house on the present location of the Great Stone Dwelling in Enfield Shaker Village. The Shakers moved this structure to its current location in 1834 to make room for their new stone dwelling house. The building was primarily used as a school building for the Shaker children, but was soon converted to a tailor’s shop after the boy’s and girl’s schools were joined into one room. In Shaker communities throughout the United States, it was customary for Shaker tailors to create the clothing for the men of the community. A brother’s standard uniform consisted of a great coat, dress coat, waistcoat, and trousers.

White-Heaton House // 1795

This transitional Federal house in Thetford was built around 1795 for an Isaac White. The house was later owned by Orange Heaton (who’s name perfectly fits the color of the leaves in the photo). The design is refined, yet stately with the enclosed, gabled, projecting entrance porch. Louvered panels and an elliptical louvered fan frame the door.

Staples-Crafts Farm // 1750

In 1688, John Staples, settled in the untouched landscape seven miles west of Boston, now known as Waban Village in the town of Newton. John was a weaver by trade but he ended up as the first public school teacher, the town clerk, a policeman, and an alderman. John married and lived in a modest farmhouse for decades here, witnessing the birth of a new nation nearby. The couple had no children of their own but raised some of Mary’s relatives including Moses Crafts, who would eventually take over the home. Craft rebuilt the house on the original foundation around 1750, constructing a colonial farmhouse two and a half stories high with five windows and two rooms across, one room wide.

Joseph Crafts died in 1821 at the age of 85, leaving no will and considerable
debts owed. The Judge of Probate ordered the property to be auctioned, and
Joseph’s son, Moses Crafts II, made the winning bid of $5.50 for the house,
barn, and a large tract of land! In 1824, Moses Craft II sold the property to his cousin William Wiswall, who gave the house a Federal period remodeling.

By the late 19th century, the home and ample farm land were acquired by William Strong and his wife Mary. William, President of the Massachusetts Horticultural Society, used the property for some time as a nursery, with apple orchards and rose gardens. After his petitioning for a train station in Waban, he parceled up the farmland into large house lots for sale, seeing the neighborhood shifting to a suburban village. He soon after built the Strong Block, the first commercial building here.