Hallowell as John A. Macdonald would have seen it in 1833. Sketch of Hallowell by John Pepper Downes 1847 Courtesy of the Prince Edward Historical Society

Hallowell as John A. Macdonald would have seen it in 1833. Sketch of Hallowell by John Pepper Downes 1847. Courtesy of the Prince Edward Historical Society




Begin your walking tour at

1. Macdonald Square at The Armoury 2015 – 206 Main Street

Ruth Abernethy’s bronze statue Holding Court unveiled and dedicated on July 1, 2015

Ruth Abernethy’s bronze statue Holding Court unveiled and dedicated on July 1, 2015


Welcome to Macdonald Square in front of TheArmoury of the Hastings and Prince Edward Regiment (Hasty P’s). Here in the square, you are standing in front of Ruth Abernethy’s bronze portrait of a young John A. Macdonald Holding Court in his first trial in the Picton Courthouse on October 8, 1834. (Learn more about the trial later in the tour.) As you will see on the plaque, the sculpture was unveiled on Canada Day 2015 to celebrate the 200th anniversary of the birth of Canada’s first prime minister, Sir John A. Macdonald, born January 11, 1815.

This site in downtown Picton was chosen to display the sculpture ofMacdonald because this is where he spent much of his time meeting and greeting people and volunteering in the community while he lived here. This is the 10th public sculpture of Sir JohnA. Macdonald and the first to portray him as a young man at the beginning of his career. The portrait was placed here as part of ongoing plans to revitalize historic downtown Picton.

When the 18-year-old John A. Macdonald arrived in Picton in 1833, he came to take over the law firm of his cousin Lowther Pennington Macpherson, who was suffering from a serious lung disease (probably tuberculosis). John had spent the last three years reading law while working in the office of George Mackenzie in Kingston. He was a bright young man who learned quickly and adjusted well to his new role as a pro tem (replacement temporary) lawyer. With the advice of his cousin – convalescing nearby on Hill Street and later in Hillier – John was able to manage the law practice and assist clients as if he were a lawyer. In those days, there was no law school. Students of law were required to article while working under the guidance of a qualified lawyer. The Law Society of Upper Canada allowed students some flexibility to practise while they were studying. Today, we would perhaps call John a paralegal.

You will be interested to know that Canada’s first prime minister had a close connection with the early Canadian militia. Two years after he left Hallowell/ Picton, he served as a soldier in the Loyalist militia at Montgomery’s Tavern in York (Toronto) during the Rebellion of 1837. In 1838 he actually defended eight young men who were on the other side in the conflict. As a result of Macdonald’s defence, they were all found not guilty and released. If they’d been found guilty, they would likely have hanged. John was 23 at the time. Many years later, Macdonald served as Canada’s Minister of Militia from 1860-1867 during the time of the Fenian Raids and theAmerican CivilWar when the country was again under threat from the U.S.

It’s also interesting to note that theArmoury served as the training facility for the Prince EdwardMilitia in preparation forWorldWar I. It was officially opened by anotherMinister of Militia, Sam Hughes, in 1914.



2. Mansion House circa 1830s – 229 to 255 Main Street (at Ross)

Walk to the crosswalk at the Regent Theatre and cross to Ross and Main Street


John Pepper Downes, 1847 sketch courtesy of Prince Edward Historical Society

John Pepper Downes, 1847 sketch courtesy of Prince Edward Historical Society


In 1833 when John A. arrived in town, the Mansion House stood at this corner. This was the most popular inn in Hallowell on the famousYork to Kingston Road, otherwise known as the Danforth Road, completed in 1802. To the right of the main entrance was the largest of five taverns in Hallowell. It was also known locally as the Hopkin’s Inn and Tavern, named after the inn-keeper.

The local magistrates, who formed the local government, would meet here frequently to discuss important matters such as cholera epidemics, agriculture, managing the obligatory service for the construction and maintenance of roads and fences, control of farm animals, rampant hooliganism, the need for a police force, and the establishment of the first district school in Picton/Hallowell. The Hopkins, Eyre, Striker, Redmond andMcFaul taverns were often used for these meetings.

Here in this Hopkin’s tavern,Macdonald volunteered as secretary for the first Prince Edward District School Board, for the Prince Edward Agricultural Society, and the Prince Edward Young Men’s Association. He was only 19.

In 1834 when the new Picton Courthouse was finally completed, the local magistrates were better able to deal with municipal and judicial matters in a more suitable setting. In those days, it was not uncommon for these leading citizens to have an occasional refreshment while discussing both legislative and administrative affairs.

This tavern was also famous in County folklore as the location of the tussle between John A.Macdonald and Dr. ThomasMoore, a local doctor. There are at lease five versions of the incident that led to indictments against Moore and Macdonald– all imaginative and questionable. The court records for their two trials on October 8, 1834 provide no details about what really happened and where it happened. It seems likely, however, that Dr.Moore was at the receiving end of one of Macdonald’s many practical jokes, but no one knows for sure, only that the trials took place andMoore was found guilty of assault – andMacdonald was not. ButMacdonald and Dr.Moore worked together before and after the trials without further incident.

The Downes’ sketch above is the only reminder of this busy coach house on the Danforth Road. The Mansion House burned down sometime in the 1850s.


3. North American Hotel circa 1835 – 297 to 299 Main Street

Walk east on Main Street (away from Armoury) to the North American Hotel at the top of the town hill.

George Ackerman watercolour of Main Street 1866 Courtesy of the Museums of Prince Edward County

George Ackerman watercolour of Main Street 1866
Courtesy of the Museums of Prince Edward County


The North American Hotel (see Union Jack) is located to the right of the frame in this watercolour by GeorgeAckerman. The scene depicts a thriving town twenty-one years after Macdonald left Picton.

This impressive building is a fine example of Loyalist/Georgian architecture, an ambitious undertaking for Hallowell in 1835 when John A. worked in the law office across the street. Built by Robert Abercrombie and leased to a series of hotelkeepers it was, like other inns on theYork/Kingston Road, a welcome sight for weary travellers.

According to E.B. Biggar, Macdonald’s early biographer, this street corner is the location of one of Macdonald’s pranks with the boys one night:

“[The]… burly and jolly-faced hotel keeper of the Mansion House named Bob Hopkins …[raced]… his horses through the village at breakneck speed. John A. and his friends conceived the idea of checking his mad career homeward by building a rail fence across the road. This being done, the boys did not have to wait long before the buggy of Bob Hopkins was heard rattling up the street. Along came the horse at his usual impetuous pace, and dashed full tilt against the fence. There was a distant roar of laughter and a stampede, but that horse was stopped and the buggy smashed, but Bob arose from the wreck a most astonished but, happily, uninjured man.

“One of the local magistrates heard of the case the next day and felt that something must be done. Somebody must be punished, and so he caused the arrest, on suspicion, of a man who was not one of the parties at all, and had not even heard of the affair. But there were some unexplained circumstances about his whereabouts on that evening. The poor fellow was actually on the point of being convicted, when young Macdonald’s sense of justice compelled him to go to the magistrate and confess that he was the ringleader, and that the accused was perfectly innocent.

“How the perpetrator managed to put the case so as to escape arrest himself is not known; but he afterwards, in telling the story, said the incident impressed him strongly with the doubtfulness of circumstantial evidence.” From the Anecdotal Life of Sir John A. Macdonald, 1891.

 4. Location of Home of Lowther Pennington Macpherson, Hallowell c. 1830 -6 Hill Street (near Fairfield and Hill Streets)

Walk along Main Street past the City Hall known as Shire Hall and further past theWexford House, Merrill Inn, and the McMullin House, some of the stately homes of Picton built during the prosperous Barley Days in the latter part of the 19th century. Turn right on Johnson Street, then left on Hill Street to Fairfield Street where Macdonald stayed with his cousin Lowther Pennington Macpherson overlooking Picton Harbour. You will find a historic plaque further along Hill Street in the park that tells of the founding of Picton.


John’s cousin, Lowther Pennington Macpherson, lived on Hill St. near this location on the Bay of Quinte (notice the Picton Court House across the bay.) He practiced law nearby at the top of the town hill. Born in 1807 during the family’s voyage to Canada, he was named after the commander of the 10th Royal Veterans Battalion (later an important defender of British North America during the War of 1812.) Lowther was eight years older than his cousin John A.

Two of Lowther’s brothers also moved from Kingston to live and work in the Quinte region. The elder of the three brothers,Allan Macpherson was a leading local businessman, militia leader, magistrate and Napanee’s first postmaster. He gained some fame in the hamlet, and was recognized locally as the “Laird of Napanee.”

JohnAlexander Macpherson was the youngest of the three brothers. He was only six years older than his cousin, but by the time John A. Macdonald was practicing law at the age of 18 in Picton, this Macpherson was running several businesses in Hillier. He too studied law and passed his law examination with the Law Society and became an attorney in Prince Edward County. He also was a merchant, magistrate and community volunteer.

When Lowther died at age 30, John Macpherson arranged to close the law practice of his brother and settle his business affairs. He later followed John A. to Kingston to become a director of the Midland District Bank and civic leader.

Like his brother Lowther, JohnMacpherson died of lung disease, possibly severe bronchitis, tuberculosis, or cholera during the many epidemics of Upper Canada. He was 35. Perhaps his most important legacy was that one month before he died, he supported his younger cousin’s entry into the legislative assembly of the Province of Canada in April 1844.

 5. TheWashburn Store (demolished 1969) – 322 Main Street

Walk back toward the top of town hill stopping just before at the municipal parkette beside Shire Hall. Here W.H. Barlett painted the scene you see in the next illustration. Trees now obstruct the once impressive view of Picton Harbour. Walk to the flashing lights at the top of the town hill where a white brick building is located.

Hallowell byW.H. Bartlett drawing in 1838 on travels through Upper Canada and published in 1842 in Canadian Scenery

Hallowell byW.H. Bartlett drawing in 1838 on travels through Upper Canada and published in 1842 in Canadian Scenery

This is the view of Picton Harbour from the top of the town hill where the Macpherson law  office was located. W.H. Bartlett, a famous English artist completed this sketch about four years after Macdonald left Picton. This, then was what Macdonald and his cousin would have seen from their office window.

To get a better view of the building where the law office was located, see the Ackerman drawing shown at Stop 3 and look for the red brick building in the bottom left hand corner of the picture showing the NorthAmerican Hotel. For years, this building was rumoured to have been where Lowther PenningtonMacpherson practiced law in the 1830s and where the Hallowell byW.H. Bartlett drawing in 1838 on travels through Upper Canada and published in 1842 in Canadian Scenery teenage John A. Macdonald assisted his cousin during his illness. This red brick building was demolished at the top of the town hill to make way for street widening in the 1960s. Although Picton lost a piece of valuable history when this happened, we now know from E.B. Biggar biographer that the building containing the law office likely burned down shortly after Macdonald left Picton in 1835.

Nevertheless, this was the location of the law office when John A. managed the Macpherson practice for two years. JohnA. knew real estate law fairly well and some corporate law, but he consulted with his cousin frequently to ensure that he was acting properly and in accordance with the laws Upper Canada. John A. enjoyed the experience helping clients and managing the law office. He gained confidence in his abilities and proved to be so popular in town that one day the town elders offered him 100 pounds sterling to stay.

His agreeable nature, civic contributions and his fun loving antics made him a legend in this bustling village in Loyalist Upper Canada. But John A. was presented with an unexpected opportunity during the summer of 1834 when his former employer George Mackenzie died during one of the cholera epidemics. John A. waited until he’d graduated from the Law Society as an attorney in 1835 before moving back to Kingston to open his own law practice. His cousin John from Hillier took over his brother’s practice briefly before moving with his family to join John A. in Kingston.

6. Eyre’s Inn and Tavern c. 1835 – 64 Bridge Street

Walk down the town hill on Bridge Street and take the first left and walk up the hill to the last remaining building of Eyre’s Inn and Tavern.

Photograph courtesy of The Settler’s Dream

Photograph courtesy of The Settler’s Dream

It is rumoured that John A. Macdonald stayed here at some point when he was working in the Macpherson law office. His family lived five miles away at the Stone Mills of Glenora so it’s conceivable that he may have spent the occasional night at this popular inn (and tavern). We do know from local legend thatMacdonald was known to walk 5 miles barefoot from his parent’s home at Glenora – like a good Scott – to save shoe-leather. He would put his shoes back on at the stone wall at the Vance farm just before the town hill.We do know that he stayed with his cousin, Lowther Pennington Macpherson at 6 Hill Street in Picton but we don’t know for how long and when.

Thomas Eyre, a United Empire Loyalist, purchased this two acre property from Reverend William Macaulay in 1816. Here he built an inn and tavern. The building you see here on this site is all that remains of much larger buildings erected in the 1820s and facing Eyre Street around the corner.

The tavern on this site was popular with local magistrates. For years, these stalwart community leaders would meet over a drink or two to enforce municipal and provincial laws and supervise services for the general welfare of the community.Active citizens of the community also met here to petition the Lieutenant Governor for changes such as petitions to rename Hallowell. Macdonald would have known virtually everyone at those meetings.

7. St. Gregory’s Church c. 1830 – 7 Church Street

Walk up the hill to Eyre’s Street and turn right to Church Street Turn right and cross Union Street to Macaulay Heritage Park Museum

John Pepper Downes’ sketch 1847 Courtesy of the Prince Edward Historical Society

John Pepper Downes’ sketch 1847 Courtesy of the Prince Edward Historical Society

According to The Settler’s Dream: “This is not the first church to be built on this site, and in fact, the parish dates back to the early days of Picton when the Reverend William Macaulay donated the site to the newly-founded congregation, named for St. Gregory. Belden’s Atlas depicts a complex of three buildings, all since demolished, which served the parish in its early years. The atlas claims that the oldest building then a school was in fact the first church. Superseding it was a more spacious church, built of stone in 1839. [It]…shows some admirable details especially in the cornice.”

8. St. Mary Magdalene Church – circa 1823 – 23 Church St

Walk west along Church Street to intersection with Union Street. Cross over to Macaulay Heritage Park Museum

John Pepper Downes’ sketch 1847 from The Settler’s Dream

John Pepper Downes’ sketch 1847 from The Settler’s Dream


Reverend William Macaulay was the first rector of the old Anglican St. Mary Magdalene Church built in 1823. The building now houses rotating exhibits, highlighting the history of Prince Edward County. The church was converted several years ago to the Prince Edward County Museum. On display is a head study of the John A. Macdonald sculpture on Main Street. It was donated to the museums of Prince Edward County by the Parrott Foundation and the Macdonald Project of Prince Edward County. Another Macdonald bust has been donated to Quinte region schools. These busts commemorate the bicentennial of the birth of Sir John A. Macdonald in 2015 and celebrate his time spent in the Quinte region.

9. Macaulay House circa 1830 – 35 Church St.

Walk next door to 35 Church Street.



Macaulay Heritage Park is a complex oftournill heritage structures and gardens. The Manse, or home of Reverend Macaulay, has been restored to the 1850’s period and provides visitors with a taste of nineteenth century life. Costumed interpreters relate stories of the Macaulay family and their times. The Stone Room is available for catered events. The grounds include a heritage orchard, gardens, cemetery and carriage house.

The original owner of the house was Reverend Macaulay UE (1794-1874) an Oxford educated Anglican minister, and philanthropist. From 1821 to 1835 he was chaplain to the Legislative Council, succeeding John Strachan in that office, but he spent most of his life as rector in the Picton diocese until his death in 1874. Reverend WilliamMacaulay was originally sent to this area from Kingston as a missionary. In 1823 he organized the Parish of Hallowell, donating the land for the church and paying for much of its construction from his own personal wealth. Rev.Macaulay’s contributions to the community were not only spiritual, but also civic, donating his own property for the construction of a school and courthouse in the early 1830s and the nearby Catholic church in 1839.

Macaulay was also instrumental in the naming of the town of Picton. There was considerable opposition to the name, however. Many prominent citizens of Hallowell signed a petition to request the legislative assembly consider renaming the combined villages of Hallowell and Picton as Port William, presumably after the ruling king of England. John A. Macdonald and his two cousins also signed this petition. Macaulay favoured the name of the famousWelsh general who died at the Battle of Waterloo. Those were the days before responsible government when landed gentry held most of the power in the province.

It is interesting to note that the names of two towns in Prince Edward County, Picton and Wellington, are lasting reminders of the importance of the Battle ofWaterloo to the early settlers of Upper Canada. Coincidentally, JohnA.Macdonald was born in the same year as the famous battle and the defeat of Napoleon in June 1815.

10. Picton Courthouse, 1834 – 44 Union Street

Cross the street and walk down York Street to Portland Streetand turn right. Walk to the front of the courthouse.


This courthouse, completed in 1834, is one of the oldest functioning courthouses in Ontario. Here in April 1834, John A. sat with his father Hugh in the public gallery at the opening of the new courthouse when the first Court of Quarter Sessions convened in the new County of Prince Edward. John A. attended these magistrates’ courts and the fall Assizes. John’s father was one of the 42 magistrates that were appointed that year by the Lieutenant Governor to run the administrative and judicial affairs of the new district in Upper Canada.

The Courts of Quarter Sessions formed not only the courts but also the municipal government in the new district. These courts met four times a year to hear the most common indictable offences, such as larceny and assault.A grand jury heard the evidence against an individual and decided if a trial was warranted. If there was enough evidence against a suspect then an indictment was issued and a twelve-man petit jury was selected to hear the case.

The Jury by John Morgan 1861 Courtesy of

The Jury by John Morgan 1861 Courtesy of


Petty Sessions handled most of the lesser legal cases, both criminal and civil without formal indictments from a grand jury or juried trials. They were presided over by two or more Justices of the Peace, who often had no legal training but were appointed by the monarch’s representative based on recommendations from prominent citizens in the districts. The Justices of the Peace would hear charges of minor offences in the court system where summary convictions were allowed. These sessions were often unruly affairs since there were often no rules of evidence, no record keeping and frequent displays of bias. One such case involvedMacdonald.According to E.B. Biggar, “Macdonald’s first case was one in which his client sued the magistrate on some trifling ground, and he often afterwards told with great gusto of the magistrate’s indignation at being thus bearded in his den [i.e. accused in his own court] and the amusement the suit gave rise to.”

Petty Sessions or Magistrate’s Court in C19th Courtesy of

Petty Sessions or Magistrate’s Court in C19th
Courtesy of


Assizes handled more serious crimes subject to more severe punishment such as execution, or life in prison. The trials were held in the fall in Prince Edward County when travelling judges would hear the cases against prisoners confined in the Picton gaol.

Anecdote of a Trial in the October Quarter Session.
John was involved in many of the civic affairs of the twin towns of Hallowell/Picton and was well liked in town. But he was well known to play pranks on his friends and acquaintances in town. One day he appeared to have gone too far with Dr. Thomas Moore, a local doctor.

Although we don’t know much about the incident, it appears likely that Macdonald likely played a trick on Moore, perhaps for political reasons. We know that Macdonald was a Tory and Moore, a Reformer. Moore had a temper and that there was a tussle. A number of local magistrates were on the scene and found sufficient evidence to lay charges against the two. Both were indicted for assault and on October 8, 1834 each faced a trial before a judge and jury in the Picton courthouse. Dr. Moore went first and was found guilty as charged. He was fined a token six pence. John went next. He defended himself before a judge and jury and was found not guilty.

The trial marks the moment when the young lawyer discovered his calling in life. Four months after the trial, at age 20, JohnA.Macdonald successfully completed his studies with the Law Society of Upper Canada and was given authorization to practice law. The trial, therefore, marks the moment when JohnA. came of age and started his career in law. He had proved that he was both effective in the courts and in the court of public opinion.

But JohnA. saw more opportunities in Kingston. In moving back there, he ended his 11-year connection with the Quinte region. The following year his cousin Lowther died on the high seas off the coast of Jamaica while still trying to find a cure for his disease. Hugh Macdonald, now realizing that the family fortunes lay with his son, moved the family to Kington the following year. John’s other cousin in the County, JohnAlexanderMacpherson, followed with his family soon after.

The court documents are available but they do not provide much insight into what was said at the trial. We know the indictment, the names of judge, members of the jury, witnesses for the defence and prosecution, and the verdict.Although there is no record of the evidence presented at trial, we do have a number of anecdotes about the event that add colour to the local legend of the much-loved John A. Macdonald.

Macdonald and the 1837 Rebellion

While John A. was arguing his case in the courtroom upstairs in the new courthouse, downstairs he was recording the vote for the highly contentious election of 1834. After the voting had taken place the same week as the trials, two Reformers were elected over their three Tory opponents. Along with their colleagues in the Reform Party, they helped to bring down the government of Lieutenant-Governor Sir Francis Bond Head by refusing to pass any new money bills.

The Conservative party won the next election, but violence erupted in Upper and Lower Canada in what came to be known as the 1837-1838 Rebellion. Democratic reforms soon followed,setting the stage for responsible (democratic) government in the British North American colonies.

As a loyal Tory, John A. not only defended colonial rule by serving in the Loyalist Militia at the 1837 rebellion at Montgomery’s Tavern, but soon after he actually defended eight of the young rebels in court and won. They may have been on opposite sides in armed conflict, but in the courts Macdonald was
their devoted advocate.

Throughout his life,Macdonald was a strong advocate of the rule of law. He said later in life
that he felt embarrassed by civil unrest in Canada and believed that reform could best be
achieved from within the British parliamentary system and the legal system.


11. First Methodist Meeting House circa 1820 – 12 Chapel Street

Walk past the front of the courthouse to Pitt Street and turn left. Go to Union Street and turn right. Walk down the hill to Mary Street and turn left. Walk uphill behind the Regent Theatre, Library and Armoury to the church you will see at the top of the hill.

Sketch from The Settler’s Dream

Sketch from The Settler’s Dream


At this location stands the impressive Picton United Church, once the home of Methodism in Hallowell.

In 1820, a New-England style meeting house stood on this site, built in the centre of town to serve the numerically dominant Methodist congregation in Hallowell. Some of the wealthiest citizens of Prince Edward County were Methodists and a number of them were notable Reformers.

John A. Macdonald, a Tory, would often entertain dinner guests with anecdotes of his mischievous youth in Hallowell. One of these stories, recovered by journalistAnneMerrill from a local newspaper, took place in the Methodist meeting house seen in the illustration.

“…on a very cold evening, I and some of the young men found on the road a dead horse frozen stiff and we thought it would be a joke to place the horse in the Methodist Church there at the end of Chapel Street, and this we did, placing it in the pulpit, seated in the chair, with its two front feet on the reading desk.

“There was [to be] held at the time a protracted meeting in the Church. Soon after the Sexton arrived and began to light up, beginning at the door and lighting the candles in their tin Sketch from The Settler’s Dream holders around the wall, and when the old sexton reached the pulpit, the one-half of the room being badly lighted and the other half in darkness, he discovered the awful apparition in the pulpit.

“Running out, he declared that the devil was in the Church. In a very short time the whole population of the town was on the street–men, women and children—but nobody was found willing to go into the building. Finally lanterns were brought and some men went in and removed the horse.

“The next day a young man of the town was put on trial, and Sir John had to sit in court and take notes of the trial. The young man was convicted of the offence and found on a chain of circumstantial evidence so complete and convincing that there was no weak spot in it, at the same time that [the] young man had nothing to do with matter.…This so impressed Sir John…that afterwards when he was Minister of Justice at Ottawa he would never allow a man to be hanged on purely circumstantial evidence.”

The moral of the story is remarkably similar to others from Macdonald’s time in Picton. It is yet another part of the local legend of John A. Macdonald, a Quinte Boy. The truth is, as Minister of Justice, Macdonald would rarely intervene in hangings even when the accused were convicted on circumstantial evidence. Justice was swift and severe in nineteenth century Canada.

The infamous 1883 Lazier double murder trial of Picton is a case in point (cf. The Lazier Murder: Prince Edward County 1884. Robert J. Sharpe).

Walk toward Main Street and turn left. Return to the Macdonald Square in front of the Armoury.

Thank you for imagining life in John A. Macdonald’s Picton

by DavidWarrick,
Chair of the Macdonald Project