Go East … Historical Day Tripping

Highway 401 is a fast moving corridor to Montreal. However, few people appreciate the wealth of day trips either side before hitting the provincial border. 

The first signs you see along the 401 going east, welcome you to “Loyalist Country”.  The word “Loyalist” will crop up frequently in this area. After the American Revolution, United Empire Loyalists (UEL), flooded into the Maritimes, Quebec, and then down along the St. Lawrence River to the Bay of Quinte and other Ontario border areas, creating Upper Canada in 1791.


Loyalist Township encompasses Amherst Island in the Bay of Quinte, named in honour of Jeffery Amherst, 1st Baron Amherst, British commander-in-chief in North America. 

Nowadays the island is famously known for its wine as Prince Edward County. It was named for Prince Edward, Duke of Kent and William IV, Queen Victoria’s father. There are at least 35 wineries to visit! All that, along with pretty villages, countryside and the impressive white sandy beaches at Sandbanks Provincial Park, in addition to sailing and fishing. Birdwatchers will enjoy this key migratory location for many species, especially wintering hawks and owls. The area is also known for Irish dry stone walls. 

Nearby is Picton, a Loyalist town named for a British Lt. General killed at the Battle of Waterloo. Its airport was originally used by the RCAF and RAF for training in WWII. Vestiges remain, and it is still used for recreational flying, filming and local motorsports events. In town stands the restored Edwardian era Regent Theatre.

From here, via the Glenora Ferry, take the bucolic Highway 33 along the shore, avoiding the 401 rush!  Highway 33 is called Loyalist Parkway, because parts were built over 200 years ago for Loyalist settlers. Loyalist heritage sites dot it, as well as First Nations communities. It was dedicated by Queen Elizabeth II in 1984 to commemorate 200 years of Loyalist settling. After Kingston it becomes Highway 2.

Napanee along the way encompasses Adolphustown, the original Loyalist Landing site.  It has the U.E.L. Heritage Centre & Park (a museum, public park, and family campground), the Old Hay Bay Church built by them in 1792 (the oldest Methodist building in Canada, a National Historic Site), and the stately Georgian Allan Macpherson House, besides the elegant town hall/market.


Kingston has a long history beginning in 1673 as a French trading post with local First Nations. Originally it was called “Cataraqui” from the Iroquois language; “Fort Frontenac”, “King’s Town” with British rule, and then “Kingston” before 1800, it was briefly Canada’s capital in 1841. Sir John A. Macdonald lived and practiced as a lawyer here. It is home to Queen’s University established in 1841, and the Royal Military College of Canada in 1876.

Heritage is a big part of sightseeing. Nicknamed the “Limestone City” due to historic use of local limestone, the lovely downtown along with its weekend farmers’ market, shops and restaurants is fun to explore. Sir John A’s home, Bellevue House, is open to the public. Fort Henry was built for the War of 1812 to defend the strategic British navy dockyards defending Lake Ontario, and later fortified to also defend the base of the Rideau Canal, a World Heritage Site. Martello Towers and a battery were added because of tensions with the USA. The western end of the La Salle Causeway has reconstructed parts of the original French fort the British destroyed in 1758. The city was also the site of many early Canadian industries. Kingston Penitentiary, a museum now, was Canada’s first large federal penitentiary in 1835, and covered extensively LivingSpaces Winter 2022 issue.

Northwest of Kingston is the hamlet of Wilton with its more than 150 year old cheese factory, one of several in eastern Ontario open to the public. Once we met actor Dan Ackroyd nearby, whose family has its roots in the area. Cottagers have discovered the Rideau Lakes area, including Margaret Trudeau. The 1810 Old Stone Mill National Historic Site in Delta will even sell you a sack of flour!

And Moving Further East

Highway 2 brings you to even more historic towns, Georgian architecture, farms and beautiful roads. This was an area first settled by First Nations and hotly contested in the French and Indian Wars because of its strategic location on the St. Lawrence River.

Gananoque, “town on two rivers” in the First Nations language, is a Loyalist settlement. It too figured in the War of 1812 and the 1837 Patriot War. Its claim to fame today is as “Gateway to the Thousand Islands”, whose beauty inspired Irving Berlin to compose the song “Always”. It is an important starting point for boat cruises through the Thousand Islands and to Boldt Castle, New York.  Live theatre is offered in the summer theatre festival of The Thousand Islands Playhouse, in two venues.  Also see the Arthur Child Heritage Museum of the Thousand Islands and Thousand Islands Boat Museum. The Thousand Islands – Frontenac Arch Biosphere Reserve here is part of the UNESCO world-wide program.

Beyond Gananoque, is the site of the first glassworks in Canada in 1839, at Mallorytown.

Prescott was founded by Edward Jessup, who fought with the King’s Royal Regiment of New York and later led his own Loyal Rangers in the Revolution. A modern bridge goes to Ogdensburg, NY, close enough to have been a base for American raids in the War of 1812, resulting in the building of Fort Wellington, now restored as a museum. It saw service during the Rebellion of 1837, and defeat of American Hunter’s Lodge members attacks during the Patriot War at the Battle of the Windmill nearby. The windmill still stands as a bulwark to those uncertain times. The St Lawrence Shakespeare Festival runs annually in the summer there.


Further on takes you to the beautiful City of Brockville. Originally called Elizabethtown, it was renamed in honour of General Isaac Brock who in the War of 1812 defeated the Americans at Fort Detroit and later died defending Niagara. Brockville was an American target in that war, and the 1866 Fenian Raids which helped prompt Confederation. At one time it had the wealthiest concentration of people in Canada. Among them were Senator George Taylor Fulford, made rich with worldwide patent medicines like Dr. Williams’ Pink Pills for Pale People. His palatial house, Fulford Place, and gardens are run by the Ontario Heritage Trust. North-West Mounted Police Inspector James Morrow Walsh was born and died in Brockville. He assured Sitting Bull and followers protection from the US army, and later fed them out of his own pay when they faced starvation. The downtown waterfront area has been redeveloped with the newly opened Brockville Tunnel, Canada’s first railway tunnel, and the Aquatarium, which is an interactive discovery centre about the ecology and history of the Thousand Islands region.

If you wander north of the 401 to the Lehigh Cemetery, you will find the graves of descents of Benedict Arnold, and their nearby home!

Don’t take my word for it! Discover for yourself our history, wineries, specialty food producers, farm stands, towns, back roads, landscapes and outdoor adventures Day Tripping East!


Author: LivingSpaces

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