Endymion Looks into the Long History of Salem’s Pickering House

Endymion Designs continues its series in partnership with Salem photographer Ziggy Hartfelder of Irish-Eye, of chronicling the rich architectural heritage of Essex County, Massachusetts. Buildings from each significant architectural period have been chosen that both exemplify its architectural characteristics AND provide a “story” that enriches our understanding of the area’s unique history.


A true indication of a building’s resilience and longevity is its ability to readapt to changing needs and uses while maintaining its unique style and defining place within its community. Perhaps one of the great attributes of Yankee ingenuity, so often found in Essex County, is their reinvention of so many of its buildings, making them appear to be in a the constant state of evolution by the generations of their inhabitants. As the writer and creator of the Whole Earth Catalogue, Steward Brand, notes in his book, How Buildings Learn, there is a certain permanence assumed in buildings that in reality is often chrysalis-like in their reformation to suit ever-changing contemporary circumstances. With its layering of changing styles, the architectural historian can peel back each successive era just as an archeologist might slowly and carefully brush away the dirt to reveal the memories within.


So is the case with the Pickering House, the oldest known existing building in Salem. Its facade betrays its origins, hidden behind a variety of features generated over succeeding generations throughout its long history. Eighteen different iterations have transformed its appearance from First Period saltbox to Gothic Revival over three and one half centuries. Even its generous lot within the city gives evidence to a much larger farm that was once over 25 acres, fronting a river now lost to reclamation, and supporting a property within Salem’s earlier and more rural times. Peeling back those layers on both the land and the house reveals a rich picture of a prominent family, pivotal from our earliest colonial days on through national leadership roles in the Revolution and the early days of the Republic. In fact, ten successive generations have occupied the Pickering House, perhaps the longest run of a single family in the same house in America.

It is not really known who built the first strands of the Pickering House. It is assumed that it was the first of ten successive John Pickerings to occupy the house. He is thought to have arrived from England in 1634, residing first in Ipswich before moving to Salem. He was a known carpenter and had already been DSC_2307commissioned to build various other structures in the young settlement.  As a newly arrived immigrant, he was granted land by the town of Salem to build his house. Researchers, however, have uncovered evidence that suggests a simple two-story structure located between the current house and barn was perhaps this first structure to be built.

The current house is believed to have been built in 1651 by the same John Pickering, yet to confuse the historian even more, forensic evidence dates some of the beams to 1660. The earlier date is based on records showing that his son, also John, was living in this house in 1651, and that the original structure was sold and moved away by oxen sometime in 1663 or 1664.

During its first major renovation in the 1670’s, the house doubled in size when the second John found a need for more space to accommodate his ever-growing family. Adding new rooms to the west, the house, as depicted in the pen and ink drawing by an unknown architectural historian (above right), now appears as a typical First Period structure that would have had two parlors on the ground floor separated by a centralIMG_8223 chimney. Decorated with downward hanging pendants as was typical of the time, the overhang on the front facade gave the occupants slightly more room on the second floor. Lead-glass, casement windows suggests a higher level of affluence as does the larger and elaborately decorated central chimney.  It is not known whether the lean-to extension on the rear roof, as depicted in later drawings was evident at this time but such a feature would have been common for this period.

The addition allowed for two generations of Pickerings to live at the house simultaneously: usually older parents or widow occupying one half of the house while the youthful family raising children in the other. Their lives were dominated by IMG_8133farming, church and civic duty. By the third generation, however, younger siblings not destined to inherit the homestead sought their livelihoods elsewhere: at sea as merchants, the clergy or civic work. It was an era of large families – both out of necessity (four Pickering children were to die in 1702 alone) and, perhaps, religious fervor. The long winters nights with little other entertainment, no doubt, played a realistic role, too.

Nevertheless, larger families put pressure on the need for further expansion. The conversion of the rear roof to a lean-to style added three more rooms while the peak gables on the front facade, as depicted in the pen and ink drawing of the 1720’s (below), added additional square footage to the garret. It was at this time that the third generation, with its nine siblings, gave way to the fourth with ten and the only owner whose name was not John.

Sketch Last

Timothy Pickering inherited the farm as a result of the early demise of his two older brothers, John and Joseph, and the decision by his next older brother, Theophilus, to enter the clergy following graduation from Harvard. Timothy was a farmer and only nineteen years old when he assumed ownership on his father’s death in 1722, but he was also a church deacon, imbedded in the local community. Salem was still a rural village dominated by fields and woods, and he quickly enlarged the farm by reacquiring parcels that had been split off by previous generations. It was into this generation with its formidable Puritan work ethic that Salem’s most famous son was born.

An eighth child and second son arrived in 1745, and would be known through history as Colonel Timothy Pickering for his rank during the Revolutionary War. He would rise to become an aide and confidant to George Washington, and later serve as Postmaster General, Secretary of War and Secretary of State in Washington’s administration – the first person to hold three cabinet positions. He would continue as John Adam’s Secretary of State but their relationship would sour, and Adams fired him in 1800. Pickering would eventually come to embody the ideals of the Federalist Party, particularly as the Virginian Thomas Jefferson’s foreign policies targeted the mercantile economy that had made Salem so wealthy.

Colonel Timothy began his meteoric rise in the inauspicious role of county clerk in Salem. A civic leader in the family tradition, he would develop a particular interest in military history and tactics, publishing a military manual for local militias. He drew suspicion from Salem Loyalists by training with the more rebellious regiment in Marblehead, and he was banned from the Salem unit for his anti-British stance following the Boston Massacre.  He was outspoken and blunt.

In those days of increasing tensions, an event in Salem could easily have become the catalyst that sparked the rebellion rather than the events in Lexington and Concord had it not been for Timothy Pickering. On February 26th, 1775, a British unit of 250 troops, sent out from Boston, landed at Marblehead with the same objective as those later units marching to Concord in the coming April: the confiscation of local munitions and firearms that would inflame the passions of American colonists. As with the later event, a local rider from Marblehead rode ahead to warn Salem’s citizens.

Armed locals gathered at the North River and raised the drawbridge to prevent the British from advancing. A tense standoff developed when the British commander ordered his troops to fire on the Salem citizens. Colonel Timothy interceded, warning the British commander that if his troops fired on them, they “would all be dead men”. The British refused to retreat, but Pickering suggested a private conference with the British commander. A gentlemanly, face-saving compromise was agreed whereby the bridge would be lowered, the British would march across in formation “a few rods”, turn around and then march back to Marblehead and thence to Boston, thereby averting the crisis. The opening salvo of the Revolutionary War would have to wait fifty days for less calm heads to react on the green in Lexington.

Years later when Colonel Timothy left government and returned to Massachusetts, he bought a farm in Wenham (below), embracing the Founding Fathers’ devotion to gardening and agriculture. In 1820 at the age of seventy five, he moved back to the house where he was born – the Pickering House – but the lure of his farm was compelling and he was often seen walking the seven miles from Salem to Wenham to tend his land. He imported from England, and planted on his farm in a pattern of a “P”, a grove of larch trees that remains today. He promoted agriculture and was instrumental in the founding of the Essex Agricultural Society whose initial Cattle Show & Fair evolved into the Topsfield Fair, America’s oldest agricultural fair.


While Colonel Timothy was serving our early presidents, his older, bachelor brother, John, maintained the house. Being without issue, the house would eventually pass to Colonel Timothy’s oldest son, also John. These two, uncle and nephew, would begin to transform the property, sub-dividing the land to the north and laying out what would become Chestnut Street, often considered one of America’s most elegant streets. IMG_8273Affluence from mercantile trade was transforming Salem from rural township to small city, and this newly acquired wealth gave merchants the opportunity to buy property here, escaping the noise and chaos of the wharves. Rising in prominence as a result, the architect Samuel McIntire introduced Federalism, the American form of British Adamesque, to Salem’s elite and began building what remains with us today.

The Pickerings themselves embraced the spirit of Federalist architecture, making alterations to the house at this time. Replacing the colonial-style casement windows with double-hung sashes and altering the roofline by decreasing the pitch of the rear lean-to gave the exterior a slightly new appearance while on the interior casing the beams and adding folding shutters and a Federal-style mantel to the fireplace IMG_8202produced a more refined appearance. Son John spent less time in Salem while his father was still alive, preferring the more cosmopolitan and career-oriented lifestyle in Boston and using the Salem address mainly as a summer home. Bookish and a master of languages, John and his wife would travel extensively in England and Europe at a time when there was a renewed interest in medieval, and in particular, Gothic architecture. Architects and critics such as John Ruskin in England and France’s Eugene Emmanuel Viollet-le-Duc were sketching, restoring and writing about Gothic architecture, resurrecting and giving new appreciation to what had previously been considered a barbaric style, giving birth to a whole new historic preservation attitude in Europe.


When John returned to Salem, he would apply a vernacular version of these Gothic features to the house on Broad Street that permanently transformed its style as we see today. Most of the work was accomplished in 1841, and included accentuating the roof peaks with the two front gables and topped with four spires. A balcony was added IMG_8205between the gables above the front door. Ceilings were raised on the ground floor rooms used for entertaining, often at the expense of comfort in the upstairs bedrooms. To improve circulation, a passage was cut through the massive chimney at the center of the house – cut at an odd angle that veers right, giving a sense that the house had been torqued slightly from the center. A new barn was added, also in the Gothic style, as was the current Gothic fence. Historians have debated whether these changes reflected the architectural tastes of the day, thereby defacing the purity of this First Period house, or whether it was a restoration to post-Elizabethan design appropriate to the 1600’s. Certainly the date of the twin front gables raises questions as they were evidently added in the 1841 renovation, but they are also assumed to have existed in the sketch above from the 1720’s. Had they been removed and later re-added?

Today, the house is owned by The Pickering Foundation, which is overseen by members of the Pickering family. The buildings are registered with the National Register of Historic Places, and the property is a part of Salem’s McIntire Historic District. Although no family members reside in the house, it is occupied by a caretaker family who are immersed in its history and keep it open to the public. The house and its occupants represent that long arc of history, from the earliest immigrants arriving from England to escape religious persecution through the civic families who built a society with structure and on through to the national stage during the Revolution and the early days of the Republic. And as history and the family evolved so too did the house, adapting to changing circumstances, needs and styles. It is hard to pinpoint a particular style, but it is really not necessary as the Pickering House represents the flow of the area’s history in its ever changing forms.


Many thanks to Tim and Linda Jenkins for showing us the Pickering House and organizing permission to photograph and use this unique property and the wonderful pen & ink drawings.  I would also like to thank Nina Wilson for the tour and rich history of her family’s property in Wenham – Col. Timothy Pickering’s country farm.

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