Celebrating over 400 Years

At over 200 years old, with roots going back 400 years, the Bailey House Inn is among the earliest buildings in Canada and rests on the estate of the Seigneurs of Port Royal.

1600s: Canada's Oldest Lordship

The Annapolis Basin has been the home of the Mi’kmaq for thousands of years. In 1605, a French expedition established a settlement at Port Royal, in the area of today’s historic town of Annapolis Royal. Later in North America, European settlers established Jamestown in 1607, Quebec in 1608 and Plymouth in 1620.

Much of the details of the first chapter of the Bailey House has been lost to history, however we believe it may go something like this…

1604 to 1610 – The Earliest Settlement of Acadia

The Seigneury (Lordship) of Port Royal was created in 1604 for Baron Jean De Biencourt De Poutrincourt (1557-1615). The Seigneury, which is the oldest feudal title in North America, was confirmed by King Henri IV of France in February 1606. That August, under the direction of Louis Hébert, the Seigneury was planted with wheat, rye, hemp and other crops. There is ample evidence that the French settlers peacefully coexisted with the Mi’kmaq First Nation. By 1610, Poutrincourt formally allocated land for settlement to 23 indivuduals.

1610 to 1703 – Seigneurial Manor of Port Royal

In 1614, the seigneury was granted to Jean de Poutrincourt’s son, Charles De Biencourt (1591-1623) and by 1623, it was claimed by Jean de Biencourt’s cousin, Sir Charles De La Tour (1593-1666). Sir Charles De La Tour arrived in Acadia in 1610 and was Governor from 1631 to 1644 and from 1653 to 1654.

Although we know that by 1686, the Seigneurial domain was here at the Bailey House Inn – the question of when this became the location of the Seigneurial Manor is a mystery. There is a good chance that the Bailey House property and the immediate neighbourhood was always intended to be reservered for the Seigneur, but there is no direct evidence of this.

It is possible that Charles de La Tour’s father, Sir Claude De La Tour (1570-1636), lived here in 1629 when he arrived with the Scottish expedition. By 1630 he was noted as living at Port Royal with his wife, a former Lady-in-Waiting to Queen Henrietta Maria of England and Scotland. However, the first resident could also have been Claude’s son, Sir Charles De La Tour, who returned to Port Royal in 1657 after his release from English captivity. He was only released after making a personal plea directly with the Lord Protector Oliver Cromwell.

Further, the precise location of the enigmatic Manor of Port Royal itself is also not clear – but we believe it once stood in, or within a few meters of, the Bailey House garden. By chance, in the 1980s, a flagstone floor was an uncovered a few meters south of our parking lot, indicating a high status building may have been right here. No formal archeology has been performed to date, so the question remains unresolved. What we know for certain is that, by 1686, Charles De La Tour’s daughter, Dame Marie de Saint-Étienne De La Tour de Belleisle (1654-1739) and her husband, Sieur Alexandre Le Borgne de Belleisle (1640-1693), the Seigneur of Port Royal, were living here at the Manor. Sieur Alexandre was also the Governor of Acadia from 1667 to 1670.

Through the Seigneuries of Port Royal and Les Mines, Dame Marie and Sieur Alexandre owned the entire Annapolis Valley – all the way to Grand Pré. We assume the original Manor was destroyed around 1690, during the Nine Years’ War (1688-1697), which was devastating for Port Royal.

1703 to 1713 – Final Years of New France

Some time around 1688 a new Manor and storehouse were built, still here at the Bailey House property, but closer to the seafront. We believe we can still the 330 year-old storehouse foundations in the basement. It appears the property continued to be associated with the Seigneurial La Tour family for a few more decades.

Francois Du Pont Duvivier (1676-1714), an Ensign and Sea Captain, became the new resident around 1703. Duvivier was known as “Sieur Duvivier” and, in 1707, married Marie Mius d’Entremont (1684-1734), the eldest daughter of Baron Jacques Mius d’Entremont of Pobomcoup, and Anne De La Tour – who was another of Charles De La Tour’s daughters. Duvivier and his family left Port Royal after it fell to the British in 1710 during the War of the Spanish Succession (1701-1714). Duvivier’s eldest son, François Dupont Duvivier (1705-1776) would later return in September 1744 to lead a siege that very nearly re-captured Annapolis Royal from the British.

Interestingly, the 1708 census indicates that Dame Marie may have temporarily moved back to the Manor. By that year, she had established another residence on Upper Saint George Street, however it was destroyed in the siege of 1707. It also appears that Dame Marie’s daughter, Anne Le Borgne, and her son-in-law, Jean-Baptiste Rodrigue, the King’s Pilot, were also resident around that time. It doesn’t seem they owned the estate, but were guests or tenants of Duvivier.

In 1708, Duvivier sold the estate to Jean-Francois Flan (1682-1733) for 200 livres. Flan came to Port Royal in 1701 as “clerk of the fort” and was considered the right hand of Governor Brouillan. He married Marie Dupuis (1679-1733) in 1705 and the couple had five children. He left Port Royal, by then Annapolis Royal, around 1713.

Early 1700s: Clash of Empires

As part of the Treaty of Utrecht in 1713, peninsular Nova Scotia became British territory. The Acadian capital of Port Royal was renamed Annapolis Royal, after Queen Anne. Life for the Acadian inhabitants was full of uncertainty. Although Jean-Francois Flan left Port Royal at this time, he owned the estate until 1733, when he sold it to Samuel Douglas (1680?-1743). Douglas was a prominent trader and owned multiple properties in the lower town. He was married three times, the first to Bathiah Douglas, whose gravestone in the Garrison Graveyard is the oldest in Canada. The gravestone is inscribed:

Here lyes ye body of Bathiah Douglass wife

to Samuel Douglass who

Departed this Life, Octo

the 1st, 1720 in the 37th

Year of her Age.

A senior member of the train of artillery at Fort Anne, Douglas may have participated in the 1710 siege. He also intended to build a wharf and this may be the same one whose remains can be found at the Bailey House today. When he died in 1743, his third wife, Anna, sold the estate and moved to Boston.

The property was then sold to Captain Edward Howe (1702-1750), a British Officer, diplomat and member of the Nova Scotia Council. In June 1744, Howe married Marie-Madeleine Winniett (1718-1793), the daughter of William Winnett and Marie-Madeleine Maisonat, whose own father was the famous French pirate Pierre “Baptiste” Maisonnat. In July 1744, during the War of the Austrian Succession (1740-1748), Howe was instrumental in repelling a Mi’kmaq attack on Annapolis Royal. Being a good distance from the fort, the Howe property may have escaped both the French attack of 1744 and the razing of buildings on Lower Saint George Street near Fort Anne in 1745.

When the capital of Nova Scotia moved to the newly founded Halifax in 1749, Howe represented Annapolis Royal at the Nova Scotia Council, the predecessor of the Nova Scotia Legislature. It is believed that Howe spoke the Mi’kmaq language. Although he worked to find mutually acceptable solutions between the Acadian/Mi’kmaq community and the British, he was nonetheless ambushed in 1750 during a diplomatic mission and died as a result.

His widow, Marie-Madeleine, continued to own the property, but it is not known how long she continued to live here or when the 1690s buildings were demolished or destroyed.

Late 1700s: Coming of the Loyalists

For the past few decades, it has been asserted that the Bailey House was built around 1770, although primary evidence has yet to surface to substantiate this claim. Regardless of the exact year, we believe it partially reuses the foundations of storehouse of the Seigneury of Port Royal, dating from around 1700. Local tradition follows that the builder was John Easson (1715-1790), who led a momentous life – his first house was destroyed by fire during the French and Indian War (1754-1763), he was kidnapped by Beausoleil and he was even an eyewitness to the Boston tea party.

The property was raided twice during the American Revolution. The first was on 2 October 1778, but was repelled. However, on 29 August 1781, American pirates were successful in their raid.

In the 1781 raid, the pirates pillaged the entire town, taking silverware, food, furniture, bedding, clothing and even the windows from the church. The town was almost defenceless as the British garrison, normally based at Fort Anne, was deployed to Charlestown, South Carolina to aid General Cornwallis. In the spring of 1782, panic broke out again as there was news that an American ship was in the Annapolis Basin and heading towards the town. Fortunately, the ship was intercepted at Goat Island and the Americans fled into the woods.

The fear of further American raids on Annapolis Royal was very real until the end of the American Revolution in 1783. In that same year, Joseph Totten (1723-1788), Susannah Totten (née Tavau) (1730-1811) and their family arrived in Annapolis Royal and bought the Bailey House. Four slaves were part of their household. Joseph and Susannah were Loyalist evacuees from New York City. Joseph set up a ship-building business, likely on the Bailey House wharf. Fortunately, Annapolis Royal and the Totten family were spared from violence during the War of 1812.

One of the most thrilling events for the Totten family was hosting HRH Prince Edward of the United Kingdom around 1794. Prince Edward was the father of Queen Victoria and is the namesake of the Province of Prince Edward Island. The Prince resided in British North America for a number of years and he is attributed as the first person to refer to all the people of what is today Canada as Canadians.

In 1816, the property that the Bailey House resides on was purchased by James Robertson. It is quite possible that he was a major investor of the Matilda – one of the most profitable privateering ships during the War of 1812. Based on the fabric and architecture of the Bailey House, it is plausible that he built our inn around 1817.

1800s: Arrival of the Aristocrats

During the early and mid 1800s, the Bailey House seemed to be the residence of choice for the cream of Canadian society, who either had business to conduct in Annapolis Royal or connected through on the way to other parts of Canada. Top Nova Scotia officials appear as regular guests.

Sometime between 1832 and 1835, Elizabeth Bailey (née Ward) (1787-1882) opened the Bailey House as an “aristocratic boarding house” which she purchased by 1837. In 1822, she married Thomas Bailey (1786-1824), but was soon widowed with three daughters to support. The name “Bailey House” comes from her, since she used her married name during its operation as an inn. She was often known as “Marm,” a name which, according to tradition, was given to her by Canadian bestselling author, Thomas Chandler Halliburton (1796-1865) – a frequent guest at the Bailey House. Elizabeth’s husband, Thomas Bailey lived a colourful life and even received an injury due to a pistol duel in 1815. He was the son of the prominent author, Reverend Jacob Bailey (1731-1808).

During Elizabeth’s tenure, the Bailey House was at a key travel centre in Canada. By 1833, Canada’s first steamship on the Atlantic coast, the Maid of the Mist, would arrive and depart at the wharves facing the Bailey House, connecting travellers with Saint John. The renowned Rose Fortune would aid travellers with their bags as they arrived and departed the Bailey House. Elizabeth’s cooking was legendary and you can even try one of her recipes listed on the Parks Canada website.

No known guest register survives from this time, but through secondary sources, we can tentatively piece together a partial guest list:

Lord William Campbell (1730-1778) – Last Royal Governor of South Carolina

Thomas Chandler Haliburton (1796-1865) – First Canadian best-selling author

George Phipps (1819-1890) and Laura Phipps (1844-1885), 2nd Marquess (and Marchioness) of Normanby – Governor and First Lady of Nova Scotia

John Spencer (1835-1910), 5th Earl Spencer – Lord-Lieutenant of Ireland

John Campbell (1845-1914), 9th Duke of Argyll – Governor-General of Canada

1900s: Renaissance

By 1910, the house was gifted to Saint Luke’s Church by Elizabeth’s last surviving daughter, Sarah Bailey (1825-1910). It was run for a few decades as a tenement, during which time its condition deteriorated. Around 1920, the stone-walled first story of the Bailey House was partially buried when the town raised Saint George Street by around three feet. Effort was taken in the 1940s by the then owner, Suzanne Halliburton (1879-1961), to restore the Bailey House to its former glory.

The house was eventually acquired in 1962 by Ruth Eisenhauer (1909-1997), a local historian, who lived here until her death. She is most vividly remembered by locals for owning the town’s only Rolls-Royce. At her death, the house and contents were gifted to the Nova Scotia Museum. However, the museum declined the offer.

Soon after, the Bailey House opened again as an inn. We have the honour of being the third owner of the Bailey House in its latest incarnation. However, the honour is not without responsibility. Maintaining a 250 year old privately-owned house which is an icon of North American history is a huge undertaking. It is our mission to ensure that the Bailey House and its incredible story is preserved for future generations.

The Bailey House in Maps

Port Royal in 1686
Future Prince William Street and Lower Saint George Street

In 1686, Port Royal was already over 80 years old. According to this map, the Bailey House is on the shore of the property owned by the former Governor of Acadia, Sieur Le Borgne (1640-1693), and his wife Marie Saint Étienne de la Tour (1654-1739). Their house seems to have once stood around the back of our garden. The dark red box shows the approximate location of the Bailey House.

At that time, Prince William Street, or “Rue Dauphin” was the principal street of Port Royal.

Annapolis Royal in 1753
Lower Saint George Street

By 1753, the Bailey House was not built yet, but the lot that is stands on was clearly established. The dark red box shows the approximate location of the Bailey House. We presume the owner at this time was Marie-Madeleine Winniett (1718-1793), who came from a prominent Acadian family. Her husband, Captain Edward Howe, a member of the Nova Scotia Council, was killed near Fort Beausésjour in 1750 while on a diplomatic mission. His death may be one of the first political assassinations of the governments that would one day form Canada.

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• 150 Saint George Street, Annapolis Royal, Nova Scotia

2025 Bailey House Inn

150 Saint George Street,
Annapolis Royal, NS B0S 1A0