This walking tour starts at the corner of Navy Street and Front Street and ends at the corner of Navy Street and King Street.

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• Follow the written guide below

Walk past the William Chisholm Historical Plaque to the end of the walking path: Instead of todays park and the pleasure boats going in and out of the harbour, you are now looking at the entrance to the harbour. This was once a bustling commercial and passenger port. The area in front of you would have been piled with wood to burn in ship's boilers. By the 1870s most steamers burned coal and the Town wanted this to be a park. They approached the owner R. K. Chisholm, son of the town's founder to see if he would sell it. He proposed a trade: the town could have the lakefront to create a park, if they agreed to close the sections of Front Street and Water Street between King Street and Navy Street so that these areas could be added to the Erchless Estate.  The Town agreed and Lakeside Park was created. 

Looking East the path was once a small road leading to a beautiful summer home. Mount Vernon built in 1900 and named after George Washington's country home. This house was owned by John A Chisholm and he and his wife Emelda Beeler Chisholm and their two daughters Hazel and Juliet lived in the US and used Mount Vernon as a summer home. Some time after John A Chishom's death in 1903 the family stopped using the house and it was rented out. It burned down in 1928 and the Town acquired the property some time later for non payment of taxes and added the land to Lakeside Park.

In July 1834, William Chisholm sold the  acre lot D, Block 21, Plan 1 to David Patterson. In 1864 Esther Thomas, widow of Merrick Thomas after whom Thomas Street is named, gave him a mortgage of $200 which was discharged in 1874. The Pattersons had eight children. Thomas was mayor in the 1890s. In 1881, Patterson’ s widow, Agnes passed it their children George H., David Jr, James, Robert, Samuel, Agnes Jr and Matilda. In 1886 it was deeded to Mary Alphonsus Reynolds, widow of Thomas Reynolds after whom Reynolds Street is named. That same year Mary and Thomas Reynolds sold it to Josephine Milbourne, spinster, for $1620 subject to mortgage. She had been renting it for several years. Since then, it has changed hands several times.

David Patterson was born in Belfast in 1807 and was apprenticed as a carpenter and shipbuilder. He came to Canada in 1826 and arrived in Oakville in 1827 to work in the Chisholm shipyard and on the building of the piers for the harbour. That was the same year that Chisholm had purchased the original 960 acres that became Oakville. He married Agnes Griggs about 1835. Her sister married John Moore and lived next door to the north. The Pattersons built a frame house on this site. In 1857 when Oakville was incorporated as a Town David Patterson was appointed Pathmaster for Ward Two. Residents were required to provide labour for the maintenance of the Town’ s streets or pay a commutation fee instead - three shillings and nine pence per day of labour, about 75 cents. It was the duty of the Pathmaster to keep account of the labour or fees. He also owned part of what is now Lakeside Park at one time and there was a small house on the corner. Patterson died in 1877. In the 1880s the building was veneered with brick and balconies were added. The original clapboard siding is still under the brick.

John Moore was born in County Armagh, Ireland, and was schooled to be a Presbyterian Minister. During his passage to Canada he developed an interest in ships and after a stint as a bookkeeper he contracted the construction of The John MacKenzie, a 180-ton four-masted schooner He married Sally, the daughter of Barnet Griggs and in 1838, built this house. His father-in-law acquired the house and enlarged it into a hotel which he leased to Jesse Belyea of Bronte. They called it the Frontier House and it served, among others, steamboat passengers. It was returned to a private dwelling 1870 and was the home of the Applebe family until 1941. In 1906 part of the house was separated and moved around the corner becoming what is now 154 King Street.

Barnet Griggs (1783-1864) and his brother, George Griggs, moved to Trafalgar Township from New Jersey in 1811, with Barnet's wife Nancy Rogers Griggs (1788-1850).

29 Navy Street was sold in 1860 to Robert Swanton Appelbe (1838-1904), the son of Squire Appelbe. He was a solicitor and a keen yachtsman. He was one of the men who organized the Royal Canadian Yacht Club in 1852 and was named the first captain of the club. Robert was the husband of Eliza Appelbe and together they had four children: Cecil Appelbe, Ernest Appelbe, Kathleen Appelbe, and Violet Twigg (nee Appelbe).

Captain Robert Wilson (1806-1888) was a mariner and sailor. Upon the death of her husband, a linen manufacturer in Ireland, Mrs. Wilson brought her ten children to Upper Canada in 1817. In 1820, at the age of fourteen, Robert started his career as a mariner. He was master of the second schooner launched from the Oakville shipyards of William Chisholm, the "Lady Colborne", in 1830. The first home he built in Oakville was on land purchased in 1832 at 23 King Street. In 1862 he built a home on Dundas Street, now Trafalgar Road, which became known as Mariner's Home. Captain Robert Wilson aided many black slaves to escape across the Lake to freedom in Canada. In recognition and gratitude for this, those he helped would gather annually at Mariner's Home. He built this home in 1883 but only lived here five years.

Captain Wilson and his home were included in Lawrence Hill's book "Any Known Blood" and a Project Bookmarks Canada plaque has been erected across Navy Street to commemorate this real site in Mr. Hill's book.

William Wilson acquired this house in 1859 near those of his brothers. It later became a general store and a hardware store. William Wilson was a younger brother of Robert Wilson who lived next door at 41. Both William and their brother George followed Robert into marine careers. William Wilson acquired this home about 1859. It had earlier stood on the east bank above the Sixteen, on the portion of Front Street which is now part of the Erchless Estate. In its first location it was probably built at the instigation of William Chisholm. On its new site, it was next door to Robert Wilson's first home on King Street, around the corner. (William and Robert married sisters from Port Nelson.)

In the early years of the 1860s, when Robert built and moved to Mariner's Home on Trafalgar Road, Captain William Wilson built a new brick house on Colborne Street (now Lakeshore) at First Avenue. Another house built by Captain William, apparently as an investment, was the store at Colborne Street to the west of Dunn Street. Initially it served as John McCorkindale's general store and later (1878) was the hardware store of James Kelley.

This house is older than the 1959 date on the plaque. This was the home of Captain Samuel McGiffin who came to Canada in the 1840s. The house was built in the early 1840's and the McGiffins likely rented it for some years before purchasing it in 1859. Samuel McGiffin's son Captain John McGiffin was also a mariner and lived in the home after his father died in 1861. John learned seafaring from his father going out on the lake when he was 12 and becoming a sailing master at just 18. He served on or captained a long list of vessels including the steamer Chippewa, the largest vessel on Lake Ontario and was chief mate serving under Captain George Brock Chisholm on the White Oak, a schooner launched from Oakville harbour on July 1, 1867. In all his years of sailing on the Great Lakes he never lost a boat or a sailor. In his later years he was Commodore of the Niagara Navigation Company which ran steamers between Toronto and Niagara.

This house was built by William Sumner a year after his house next door on William Street.

65 Navy Street as well as the adjoining lot on William Street were bought from William Chisholm by William Johnson Sumner (1797-1841) in 1831 for 20 pounds, or about $80 at the time. He was the son of Thomas Sumner, a soldier who fought under General Wolfe at the taking of Quebec City in 1759.

In 1832 he built this house and sold it after 8 years for 100 pounds. The Sumners continued to live in the house around the corner on William Street. William Sumner had been the proprietor of the Grove Inn in Nelson, which is now Burlington. Then he leased the Oakville House from his good friend William Chisholm. It was located on the site of Paradiso Restaurant on Lakeshore Road. Sumner Street, which is the south side of George’s Square, is named after him.

Matilda Sumner, a daughter of William Sumner, married Samuel McGiffin, the brother of Captain John McGiffin, who lived next door. In 1873, Matilda and Samuel purchased this house, which had been Matilda’s childhood home. Unlike his brother and father, Samuel McGiffin was not a mariner, rather he was a hardware merchant. His store was in what had been the original St Jude’s building on the northwest corner of Thomas and Lakeshore. By that time the congregation had moved to its current location. The original St Jude’s had been built by the Methodists and sold to the Anglican Congregation when the Methodists found they couldn’t afford it. The building was torn and replaced with a branch of the Merchants Bank, later the Bank of Montreal. A few years ago it was remodelled to become a clothing store.

The Murray House Hotel, known at different times as the Canadian Hotel, has passed through the ownership of John Williams, James Teetor, other proprietors, and then to Murray Williams.

The Murray House Hotel stands on the site of a home of Captain Nicholas Boylan, second master of the "Trafalgar", the first schooner built in 1857 by John Williams, brother of Captain Hiram Williams. It opened for business on December 15, 1857.

Originally named the Canadian Hotel, it offered its patrons twenty-one bedrooms (many only six feet by six feet) and four parlours. For the security of his customers' valuables, John Williams provided hidden cupboards in the cellar stairway.

John Williams sold the hotel to James Teetor in 1867, for $2,500, and returned to operating the Oakville House at the corner of Navy and Lakeshore, which he had previously owned. He had also been proprietor of the Railway Station Hotel which he built in 1856.

In 1896, the Canadian Hotel returned to the Williams family having been purchased by Murray Williams, John's nephew. It was Murray who changed the name to The Murray House Hotel. Murray Williams brought the hotel back to the standards set by his Uncle John since the hotel had gone downhill under a dozen proprietors since James Teetor.

Standing in lawns, with a fountain in the centre, it generously supplied wagon sheds for the use of customers. It was Murray Williams who introduced the automobile to Oakville, to begin the demise of the wagon.

This house was built about 1849 by George King Chisholm who was born in 1815 at Nelson Township. In 1840, he married Isabella Land, granddaughter of Robert Land, the founder of Hamilton. They had eight children, five of whom survived to adulthood. The family moved back to Oakville in 1847, and in 1848 purchased the lot on which this house stands from the Gore Bank. The house was built about 1849 and was one of the first brick houses in town.

In 1857, the year in which Oakville became a town, and George King Chisholm its first mayor, he sold the house to Dr. Elwy J. Ogden and his wife Mary, and moved to a new home which he had built at his farm west of the Sixteen. Ogden, in turn, sold the home in 1868 to Richard Shaw Wood and Isabella Wood. Wood, a native of Bermuda, had come to Oakville in the 1850s and founded the Oakville Oil Refinery on Trafalgar Road across from MacLachlan College. Wood added an addition to serve as a bank, though there is no evidence that it did.

The home was sold again in 1878 to Mary Ann and Thomas Patterson. Mary Ann was a milliner and Thomas a tailor. Thomas Patterson became mayor of Oakville in 1894. In the early part of the twentieth century the house became the home of Captain Maurice Fitzgerald who became a coal and lumber dealer in Oakville. He lived in the house until his death in 1931.

Some time after that the house became known as "Glen Prossen".

Jeremiah Hagaman came to Oakville in the 1850s and immediately set up a carriage making factory on the slope behind his home. At one time he owned nearly this entire block of land. His Oakville Carriage Works company took three prizes at the Agricultural Exhibition in Toronto in 1856 for the best two horse pleasure carriage, the best two horse pleasure sleigh, and the best two horse wagon. Hagaman also became involved in growing strawberries in Oakville. In 1869 one of his patches of strawberries yielded 2200 quarts in one day. In that year Oakville was estimated to have produced nearly 125 tonnes of strawberries. The home was sold to Benjamin Hagaman in 1871 who was part owner of Gage and Hagaman, a lumbering and flour milling company. in 1899 the house was again sold, this time to Thomas Hagaman, a carpenter  who owned it until 1942. 

This home bears the name of George K. Chisholm, the oldest son of the founder of Oakville, and the first mayor of Oakville. George was one of the first pupils at Upper Canada College and also served as the Sargent at Arms of the Legislature of Upper Canada of the 1837 rebellion. This property may have been a general retail store around 1875 however this is not certain. Likely first building on this site was barn belonging to his father William Chisholm .

William Chisholm in his original plan for the town designated this area to be the Market Square. He had also designated land for George's Square and the cemetery. When the town council of Oakville came into existence in 1857 they secured the title to the property and developed ambitious plans for a Market Building. However they could not immediately carry out these plans and instead decided first to build a town lockup at a cost of $1528 that could be turned later into a fire station. Prison cells were built on the lower floor and council chambers on the upper floor. In 1862 work on the larger Market Building was complete: it was two storeys high and 84 feet by 36 feet, and was divided into market stalls on the main floor as well as the town armoury at one end. The upper floor was an auditorium that could hold 500 people. It was also the site of an annual agricultural fair. The market building also became a place to temporarily house new immigrants who arrived by boat with little or no resources of their own. The Lockup burned to the ground in 1876 and part of the Market Building was temporarily remodelled into a new Lockup and Council Chambers. in 1885 it was further remodelled to include a fire bell and fire hall. The town hall building as it became know burned down in December 1913 destroying the records and the original seal of the town.

Alan S. Chisholm was the son of William Chisholm  He wanted to reroute the driveway of the Erchless Estate to exit onto King Street. His mother was vehemently opposed to this. He arranged for her to go on an extended vacation and when she returned the new driveway exit was in place. He also said to have constructed the white gates at the entrance gates. He was one of the founders of the Tennis Club in 1903 which became the Oakville Club in 1908. He and Murray Williams of the Murray Hotel were the first two residents of Oakville to own automobiles. The Coach House consists of the Carriage House and and attached Gardener's Cottage: they have been renovated to create flexible indoor and outdoor space for museum programs and events.

This is the location of the Oakville Historical Society offices since 1992. This was originally two cottages  built in 1952 for Julie Chisholm and Hazel Chisholms Matthews,  great granddaughters of Oakville's founder William Chisholm. Their mother purchased the Erchless Estate after the death of Alan Chisholm and removed the driveway he had constructed through this garden. Hazel is the authour of the book “Oakville and the Sixteen”, a wonderful history of Oakville and the source of much of the information in this tour. The book can be purchased through the Oakville Historical Society.