Derek Strahan

Aside from running the Lost New England blog, Derek Strahan is the author of two books: Lost Springfield, Massachusetts and New England Then and Now, along with being the host of the Western Mass History podcast. Derek is a graduate of Westfield State University, with degrees in English and Regional Planning, and he currently works as a land use and environment planner in Western Massachusetts. Derek also serves on the board of directors of the Springfield Preservation Trust, and he lives in Western Massachusetts with his wife Melissa and their two sons.

Aaron Bascom House, Chester, Massachusetts (2)

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The house across from the corner of Skyline Trail and Bromley Road in Chester, Massachusetts, in April 1938. Photo by Arthur C. Haskell, courtesy of the Library of Congress, Historic American Buildings Survey Collection.

The house in 2024:

As explained in more detail in the previous post, this house was built in 1769 as the home of the Reverend Aaron Bascom, the first pastor of the church in Chester. He lived here until his death in 1814, and then in 1832 it was purchased by Dr. Thaddeus DeWolf. It would remain in his family for over a century, and during this time several of his children went on to become prominent figures. His oldest son, Oscar DeWolf, became a physician and moved to Chicago, where he served as the city’s commissioner of health. Thaddeus’s youngest son, DeWitt C. DeWolf, was active in state politics during the early 20th century, including serving as executive secretary to Governor Joseph Ely in the early 1930s, and as the state commissioner of labor and industries.

DeWitt DeWolf died in 1935, and the top photo was taken three years later as part of the documentation of this house for the Historic American Buildings Survey. It was still owned by his family at the time, but a few months later the property was put up for auction. The house had several other owners during the 20th century, but it has been vacant for many years. All of the other outbuildings on the property are gone, and the land around the house is overgrown with trees. The historic house still has many of its original features, including the 12-over-8 windows on the second floor, but overall the house is in poor condition, as shown in the second photo.

Aaron Bascom House, Chester, Massachusetts

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The house across from the corner of Skyline Trail and Bromley Road in Chester, Massachusetts, in April 1938. Photo by Arthur C. Haskell, courtesy of the Library of Congress, Historic American Buildings Survey Collection.

The scene in 2024:

This house is one of the oldest surviving buildings in Chester, and it was built in 1769 as the home of the Reverend Aaron Bascom, the first pastor of the town’s church. The town had been incorporated several years earlier in 1765, but it was originally named Murrayfield, although it was later renamed Chester in 1783. At the time, this area on modern-day Skyline Trail was the town center. It was located along a ridgeline of rolling hills between the Middle Branch and West Branch of the Westfield River, and it was fairly close to the geographic center of the town. The center consisted of the meeting house, a schoolhouse, Rev. Bascom’s house, and several other nearby homes.

Aaron Bascom was originally from Warren, Massachusetts. He graduated from Harvard in 1768, and a year later he accepted the position as the pastor of the church here in Murrayfield. He was ordained on December 20, 1769, at the age of 23. According to the 1963 publication The First Congregational Church of Chester, his compensation included an initial settlement of 70 pounds, along with an annual salary of 40 pounds for three years, which would then increase five pounds per year until it reached 60 pounds. In addition, he was provided with firewood and, most significantly, a house, which is shown here in these two photos.

The house is typical for mid-18th century homes in Massachusetts. It features a front façade with four windows and a central door on the first floor, and five windows on the second floor. It originally had a large central chimney, but as was often the case, this chimney was later removed in order to create more space for a staircase and entry hall. Over the years, the exterior of the house also saw alterations and additions. The shutters in the top photo would not have been original to the house, and it seems likely that the Greek Revival style front entryway was probably a mid-19th century alteration.

Aaron Bascom lived here until his death in 1814, and the house was later purchased by Dr. Thaddeus Kingsley DeWolf in 1832. He was a noted local physician, and he lived here with his first wife Correlia Benham and their children Oscar, Homer, Sarah, and Martha. Correlia died of dysentery on August 7, 1847, and young Martha likewise died of dysentery five days later. However, Dr. DeWolf remarried rather quickly. Less than two months later, on September 28, the 46-year-old widower married 19-year-old Mary Phelps. They had two children together: Henry Clay DeWolf, who was born in 1850; and DeWitt Clinton DeWolf, who was born in 1864. DeWitt is known to have been born in this house, and the older children presumably were as well.

By the time the younger children were born, the town of Chester had undergone significant changes. In 1841 the Western Railroad was built along the West Branch of the Westfield River, in the southern and western part of the town. This spurred new developments in the valley, with the village of Chester Factories eventually becoming the town center, in place of the old town center here on Chester Hill, as it came to be called.

This shift was part of a broader trend in the rural hilltowns of Western Massachusetts. With more productive farmland available in the west, and new opportunities in the nation’s industrial cities, many towns and villages experienced population decline in the second half of the 19th century. Among those who left the area was Dr. DeWolf’s oldest son Oscar. He went to medical school, served as a surgeon in the U.S. Army during the Civil War, and then moved to Northampton before relocating to Chicago in 1873. There he became the city’s commissioner of health, a position that he held for 14 years.

During that time, Oscar’s younger half brother DeWitt joined him in Chicago, moving to the city around the late 1870s when he was 15. Rather than pursuing medicine like his father and brother, DeWitt went into business. He first worked for a shoe company, but then became involved in the coal industry, eventually serving as president of one coal company and vice president of another.

However, both brothers would eventually return home to Chester in their later years. Oscar left Chicago in 1891 and moved to London, where he practiced medicine for 12 years before retiring and moving back across the Atlantic to his old hometown. He had inherited the family home after his father’s death in 1890, and the 1894 county atlas indicated that he owned several other nearby homes. When he returned to Chester in 1903, he appears to have moved into the neighboring home at 346 Skyline Trail, which still stands just to the left of the old house, out of view in these photos.

Oscar DeWolf died in 1910, and then in 1915 his brother DeWitt moved back to Chester. Because DeWitt owned multiple properties, none of which had street numbers at the time, it is difficult to trace exactly where he lived, but it was apparently either his birthplace house here in these photos, or in the house next door that his brother had lived in. It seems that, over the course of his 20 years in Chester, he may have lived in both houses at different times.

The 1920 census does not indicate which house DeWitt DeWolf was living in, but it shows him in Chester with his wife Harriet and their daughters Elsie, Louise, and Virginia. Their household also included James H. Ellis, who was listed as a lodger. He later married their oldest daughter Elsie in 1926.

Shortly after his return to Chester, DeWitt DeWolf became involved in politics. He served in a variety of town offices, but he was also active in the state’s Democratic Party. He was a delegate at the Democratic National Convention in 1924 and again in 1928, and both times he was a strong advocate for New York Governor Al Smith, who earned the party’s nomination in 1928 but ultimately lost to Herbert Hoover in the general election. During the 1930 state gubernatorial election, DeWitt campaigned on behalf of his friend Joseph B. Ely of Westfield. Ely won the election, and he served as governor from 1931 to 1935. Upon taking office, Ely appointed DeWitt as his executive secretary, and DeWitt later became the state commissioner of labor and industries.

Despite working on Beacon Hill, DeWitt DeWolf continued to live here in Chester. His wife Harriet had died in 1922, and by 1930 he was living alone, probably in the house next door to this one. A 1930 article in the Springfield Republican, written after his appointment as executive secretary to Governor-elect Ely, indicated that his daughter Elsie was living in the old house, and also implied that DeWitt was not living in it at the time. However, DeWitt died in 1935, and the newspaper coverage stated that he died in the house where he was born, suggesting that at some point before his death he moved back into the old house.

The top photo was taken in April 1938, a few years after DeWitt’s death. The family still owned the house at this point, and the outbuilding on the left even had a sign that said “DeWitt C. DeWolf.” The building was photographed as part of the Historic American Buildings Survey, a Depression-era federal program that documented historic resources across the country.

The property was evidently sold a few months after the photo was taken, based on an auction notice that was published in the Republican in September 1938. The house would subsequently change hands several more times over the course of the 20th century, and in 1988 it was added to the National Register of Historic Places as a contributing property in the Chester Center Historic District. This historic district is comprised of several other historic 18th and early 19th century buildings that all date back to when this small village was the town center.

The photographs that accompanied the National Register nomination form in the 1980s show the exterior of the house in reasonably good repair. However, the house has since been vacant for many years. All of the barns and other outbuildings are now gone, the property is overgrown, and the house itself is badly deteriorated. As shown in the second photo, the ground floor windows and doors are boarded up, and there is a sign next to the front door from the board of health, stating that it is unfit for human habitation. It is an important historic house, but in its current condition it is in danger of being permanently lost.

John C. Lee House, Salem, Massachusetts

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The house at 14 Chestnut Street in Salem, probably around 1890-1910. Image courtesy of the Phillips Library at the Peabody Essex Museum, Frank Cousins Glass Plate Negatives Collection.

The house in 2023:

These two photos show the house at 14 Chestnut Street in Salem, which was built in 1834-1835 as the home of John Clarke Lee. It is one of the newer houses on Chestnut Street, as most of the other homes were built in the first few decades of the 19th century. As a result, it is architecturally different from most of the other homes. While the rest of the street consists primarily of symmetrical, three-story Federal-style homes with hipped roofs, this house is an early example of Greek Revival architecture. It features a gabled roof, and the front façade is decorated with four pilasters that give the house something of the appearance of an ancient Greek temple.

John Clarke Lee was a prominent merchant and banker who later became a partner in the Boston-based investment banking firm of Lee, Higginson & Co. He was about 30 years old when he moved into this house, and by this point he and his wife Harriet already had a large and growing family, with five young children. They subsequently had five more children, and in total all but one of their children lived to adulthood. Among their children was George Cabot Lee, whose daughter Alice Hathaway Lee became the first wife of Theodore Roosevelt.

The house remained in the Lee family for nearly a century. John died in 1877 and Harriet in 1885, but their son Francis inherited the house. He was living here when the top photo was taken around the turn of the 20th century, and he was responsible for adding the porch at the front door, as shown in the two photos. He died in 1913, and his widow Sophia subsequently sold the house in 1924.

The next owner of the house was Frank W. Benson, a prominent Impressionist painter from Salem. He was in his early 60s when he purchased the house, and by this point he had established himself as one of the leading American painters of the early 20th century. Benson was known for his portraits, along with en plein air landscapes of the seacoasts and mountains of New England. He lived here in this house until his death in 1951, at the age of 89.

Today, the house is still standing, with few exterior changes since the top photo was taken more than a century ago. Even the tree on the far right side of the scene appears to be the same one in both photos. Along with the rest of the street, the house is now part of the Chestnut Street District, which was added to the National Register of Historic Places in 1973.

James B. Bott House, Salem, Massachusetts

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The house at 18 Chestnut Street, at the corner of Bott Street in Salem, probably around 1890-1910. Image courtesy of the Phillips Library at the Peabody Essex Museum, Frank Cousins Glass Plate Negatives Collection.

The house in 2023:

These two photos show the house at 18 Chestnut Street, which was built around 1800 or possibly earlier. It was originally owned by saddler James B. Bott, and according to the building’s Massachusetts Cultural Resource Information System (MACRIS) form, it was likely used as a multi-family residence. It had a number of occupants throughout the first half of the 19th century, but the most famous was author Nathaniel Hawthorne, who lived here with his family in 1846 and 1847 while serving as Surveyor of the the Port of Salem at the Custom House on Derby Street. This house was too small for the Hawthornes, though, and in 1847 they moved to a house on Mall Street, where Nathaniel would later write The Scarlet Letter.

The house was eventually converted into a single-family residence in the late 19th century, and the top photo was taken sometime around the turn of the 20th century. It was taken by photographer Frank Cousins, who extensively documented the historic houses of Salem and other towns in the region. As the bottom photo shows, very little has changed about this scene since then. The house is still standing, as are the other surrounding homes, and Chestnut Street as a whole survives as one of the best-preserved historic streets in New England. The Bott House, along with the other homes on Chestnut Street, is part of the Chestnut Street District, which was added to the National Register of Historic Places in 1973.

Chestnut Street, Salem, Massachusetts (2)

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The view looking east on Chestnut Street from near Pickering Street in Salem, around 1890-1910. Image courtesy of the Phillips Library at the Peabody Essex Museum, Frank Cousins Glass Plate Negatives Collection.

The scene in 2023:

These two photos were taken from near the same spot as the ones in the previous post, but facing the opposite direction. This view of Chestnut Street, looking east toward Cambridge Street, features a number of early 19th century homes. Starting in the foreground on the right side is a double house at 21-23 Chestnut Street, which was built in 1814-15 for John and Henry Pickering. They were the sons of Timothy Pickering, a prominent politician who served in several different Cabinet positions, including as Secretary of State under George Washington and John Adams.

Although built for the Pickering brothers, they evidently did not own these houses for long, because each properly changed hands several times over the next few decades. By the 1830s, the house closest to the foreground, at 23 Chestnut, was owned by Robert Stone, while the adjoining house at 21 Chestnut was owned by Elisha Mack. In 1833, during President Andrew Jackson’s visit to Salem, Robert Stone hosted a reception here at his house, which Jackson attended along with Vice President Martin Van Buren, several Cabinet secretaries, and other dignitaries.

Further in the distance on the right side of the street is 19 Chestnut, which is visible in the center of both photos. This three-story, wood-frame house was built around 1805, and it was originally the home of merchant Israel Williams. Later in the 19th century it was owned by another merchant, Henry W. Peabody, and then in the early 20th century it was owned by architect William G. Rantoul.

Today, more than a century after the top photo was taken, these houses are still standing, as are the other ones further in the distance on both sides of the street. Chestnut Street survives as a well-preserved example of Federal-style architecture, and it is the centerpiece of the Chestnut Street District on the National Register of Historic Places. However, this scene is also notable because of the elm tree that still stands in the foreground. During the 19th and early 20th centuries, the street was lined with elms. Most of these were subsequently lost, likely due to hurricanes and Dutch Elm Disease, but this tree has survived, and it is still easily recognizable from its appearance in the top photo.

Chestnut Street, Salem, Massachusetts

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The view looking west on Chestnut Street from the corner of Pickering Street, around 1906. Image courtesy of the Library of Congress, Detroit Publishing Company Collection.

The scene in 2023:

During the late 18th and early 19th centuries, Salem was one of the most prosperous seaports in the United States. This was reflected in its architecture, which included many large, fashionable Federal-style homes that were built for merchants and other wealthy Salem residents. Many of these homes are located on the streets immediately to the west of downtown Salem, including Chestnut Street, as shown in these two photos.

Chestnut Street was laid out in 1796, and over the next few decades it was developed with stately homes. Only one house on the street is known to have been the work of prominent Salem architect Samuel McIntire, but his influence is clearly evident in the designs of the other houses here. Many of the houses are brick, although some are wood, and they are generally three stories high, have a hipped roof, and have a roughly square footprint. Most were designed as standalone single-family homes, but there are a few that were built as adjoining two-family homes.

By the time the top photo was taken at the turn of the 20th century, the street was already recognized as an important Salem landmark. Not only were the houses themselves significant, but the streetscape itself was also notable for the many elms that lined the street, creating a tunnel-like effect, as shown in the top photo.

Sadly, nearly all of the elms are gone now, likely as a result of Dutch Elm Disease. Today, the street is still lined by trees, but their lower canopies do not have the same effect that the elms once had. Despite the loss of the elms, though, not much else has changed in this scene. The tree cover makes it hard to tell, but all of the homes in the top photo are still standing. The street is one of the finest collections of Federal-style architecture anywhere in New England, and it forms the centerpiece of the Chestnut Street District, which was added to the National Register of Historic Places in 1973.