Benjamin Bosworth House // 1800

One of the most unique houses in Connecticut is this massive Federal style residence located in the small town of Eastford. Built next to the Congregational Church of Eastford (1829-2023), which burned down in 2023 by arson, the massive house has been known as both the Benjamin Bosworth House and Squire Bosworth’s Castle due to its first owner, Benjamin Bosworth (1762-1850). According to the Bosworth Family, the house was built in 1800 by Bosworth was a wealthy merchant, who hired Vini Goodell, a local carpenter to design and build the large Federal home. The house was completed by 1801 when the local Masonic group met in the building. As Bosworth was also a merchant, he used the basement as a storeroom. The house is also unusual for its monitor roof, a rarity in Federal period construction, which reads like a second structure on the house, due to the building’s size. After Bosworth’s death, the house was occupied by his niece, and was later purchased by Elisha Grant Trowbridge in 1897. Trowbridge was a grand-nephew of General Nathaniel Lyon (1818-1861), a local hero who was the first Union general killed during the Civil War. Trowbridge, an engineer, lived here until he died in 1963 at the age of 96. Later owners have had the monumental task of restoring and maintaining this behemoth of a house, to great success.

Sumner-Carpenter House // 1806

I don’t think any state does the Federal style as well as Connecticut (Massachusetts is a close second)! This is the Sumner-Carpenter House, a high-style example of a Federal residence that is located on the backroads of the small town of Eastford, Connecticut. The house was built in 1806 for John Newman Sumner (1775-1831) who resided here until just before his death. The elaborate Federal period house was sold out of the family. After trading hands a half-dozen times, the property was purchased by David and Harriet Carpenter in 1881. The property remained in the Carpenter family for generations, and remained as such after Orlo Carpenter (1865-1938) was killed in the collapse of a barn during the hurricane of 1938. Architecturally, the house has all of the hallmarks of the Federal style, with the symmetrical main facade five bays wide, with a center entrance flanked by wide sidelights, and topped by a fanlight transom and corniced entablature. The window above the entrance is in the Palladian style, with a rounded center window flanked by narrower sashes. The house is very well preserved and was listed on the National Register of Historic Places for its architectural quality and preservation.

Michael Richmond House // c.1814

When the town of Ashford laid out a road across the land of Abner Richmond, he saw it as an opportunity to gift the newly organized plot across the road to his eldest son, Michael and his new wife, Polly as a wedding gift. Michael Richmond (1786-1881) built this Federal style house across the street from his father (see last post), likely employing the same builder, who employed similar design elements for both homes. In early life Michael learned saddle-making and afterward engaged in the manufacture of cloth, also axes. He was also engaged in staging and turnpike building, and in the mercantile business, until he retired at 60 years of age. He was a man of all trades! The house is now home to BOTL Farm, a pasture-based, sustainability-focused livestock farm that raises pigs, lambs, goats, and chickens ethically. Gotta love seeing farming coming back to Connecticut’s “Quiet Corner”!

Abner Richmond House // c.1803

This high-style Federal house sits across from the former Westford Baptist Church in Ashford, Connecticut. The house was built around 1803 for Abner Richmond (1761-1834) and his wife Eunice, who purchased 92-acres of land here one year earlier. Abner descended from John Richmond (1594-1664), one of the original white settlers of Taunton, Massachusetts in 1637. About ten years after he built his farmhouse, the town of Ashford paid the Richmond’s money for hardship caused by laying out a road right in front of the homestead. This 1812 occurrence possibly allowed the couple to invest further into the property, where they converted some of the rooms into a tavern, which was later accessible by the new Boston and Hartford Turnpike. The turnpike began in East Hartford and made its way through Ashford before winding its way to Boston. The house was documented as having 19th century stenciling on the walls, which survived underneath wallpaper (go figure). The new owners have clearly given the Richmond House some love and care, down to the perfect paint color.

Mixer Tavern // 1710

Photo from real estate listing.

One of the most historic houses in Ashford, Connecticut was listed for sale! The house at 14 Westford Road dates to 1710, when John Mixer purchased the property which at the time totaled 100 acres, and applied for a license to operate a tavern. John Mixer was born in 1668 in Watertown, Massachusetts and married Abigail Fiske in 1695. Mixer worked as a tanner in Watertown before moving to Connecticut, becoming the first settler of Ashford in 1710. Mixer became Ashford’s first Town Clerk, Treasurer, Tavern Keeper, Select Man, and Deacon. Mixer and his family would eventually move to Suffield, Connecticut, but the old tavern remains in impeccable condition, largely due to its later owners and preservation as an inn and restoration in the 1920s.

Haven Avenue Cottages // c.1877

When Andrews Point in northern Rockport, Massachusetts, was opened for development by speculators Eben B. Phillips and George Babson, they envisioned the colony, “Ocean View” as a rival to other nearby summer colonies of Beverly Farms, Gloucester, and Magnolia. Roads were laid out and house lots were plotted with larger lots for big summer cottages along the coast and smaller cottage lots at the interior of the development. The rocky coast and more limited access compared to its rivals, caused Ocean View to lack in sales, but there are still some great remaining cottages to be found here. These two early cottages are great surviving examples of the modest, middle-class homes for summer residents. These two charming Victorian cottages sit side-by-side and were owned by an L. Brigham and Benjamin Lewis and both are in a great state of preservation 150 years later.

Bailey Cottage // 1896

In 1896, Edward L. Bailey, a carpenter and housebuilder, erected this cottage on Haven Avenue in Rockport, Massachusetts. Bailey resided in the house, likely year-round and ran a store on the nearby main street. His cottage served as both a residence and an advertisement for his skilled carpentry, which likely offered him commissions for other cottages nearby. Bailey was also selected as the builder for the town’s Carnegie Library in 1907. The cottage blends Queen Anne and Shingle styles effectively under one roof.

Eben Phillips Cottage // c.1877

In the mid-1800s, Rockport, Massachusetts was best-known as one of the main ports for the quarrying and shipping of fine granite up and down the east coast of the United States. While the rocky coastline made granite a prime industry, the natural scenery also made the coastal areas desirable for residential development. While many of the coastal developments here never took-off as they did in nearby Gloucester, Magnolia, and Beverly, there are some notable summer colonies that sprouted up! In 1855, Eben B. Phillips an oil dealer in Boston, purchased undeveloped wooded lots and pastures, and slowly began to lay out roads and survey for developable lots for summer cottages on a peninsula near Pigeon Cove. The development was named “Oceanview” and it was marketed as the extreme point of Cape Ann. Development was very slow to materialize, and started in earnest in the 1870s. Eben Phillips built this summer cottage before 1877 (possibly as early as 1850), where he would spend summers until his death in 1879. The cottage retains much of its original character and is a rare survivor of the rustic style cottages which were built before the phase of larger Shingle and Queen Anne residences were built in later decades.

Rockridge Cottage // c.1830

Few houses in Rockport, Massachusetts showcase the town’s history as a granite exporter as well as this large residence on the appropriately named Granite Street. The history of this dwelling goes back to 1828 when a young Samuel Parker (1801-1878) married Jane Boyd Rowe that year. From this marriage, Samuel and Jane inherited her family’s farmland here, which worked well for her new husband’s ambitions. Samuel Parker was engaged in granite quarries in Quincy, Massachusetts before moving to Rockport to establish a business here. In Pigeon Cove, Samuel worked as a foreman for the Pigeon Hill Granite Company and clearly used some of the granite quarried on the site to erect this stately home by around 1830. Samuel would later leave his wife for about 10 years to participate in the California Gold Rush from 1850-1860, but returned due to his older age. Their granite home became known as Rockridge Cottage through the subsequent generations of owners, all descendants of Samuel and Jane. The dormers and Victorian-era portico at the entrance were likely added in the latter decades of the 19th century.

“The Old Castle” // c.1712

Located in Pigeon Cove, the northern section of Rockport, Massachusetts, the “Old Castle” is an iconic landmark in the charming coastal town. The exact year it was built is not known, but it is believed to have been built in 1712 by Jethro Wheeler (1692-1755), a shoemaker who settled here from nearby Rowley. In 1724, Jethro deeded the property to his son Benjamin, and he moved out of town. Benjamin, is turn sold the property to his son Benjamin in 1769. Benjamin Jr.’s son, John D. Wheeler in 1792 inherited the property and added the lean-to/kitchen room to the rear to create the present saltbox roof form. Various Wheelers continued to own the Old Castle for another hundred years. The property was gifted in 1929 to the Pigeon Cove Village Improvement Society, and is presently under ownership of the Sandy Bay Historical Society, who manage the property as a house museum. The house with its overhanging second story reads like a garrison, a common element in First Period houses in Essex County.