Eleven days in eastern Canada: four cities on one railway line, getting more French as you go

Land, drop the bags and go east. The Distillery District is five hectares of Victorian industrial brick that was Gooderham and Worts, at one point the largest whisky distillery in the world, closed in 1990 and reopened as a pedestrian precinct of galleries, cafes and small theatres. No cars. Late afternoon is the time, when the light is on the brick.

Eat there or walk west towards Front Street, then finish on the tower after dark. The CN Tower held the record for the tallest free-standing structure on earth from 1975 until 2007 and is still the tallest in the Americas at 553 metres. The lift takes under a minute. At night the grid below turns into the view that justifies the ticket, and there is a glass floor on the way down.

Book a timed slot in advance in summer. The walk-up queue on a warm evening runs over an hour.

North to Bloor Street. The Royal Ontario Museum is the largest in Canada and its strength is breadth: dinosaurs, a Ming tomb, Northwest Coast carving, ancient Egypt and a bat cave, all inside a Victorian building with a great fractured crystal of aluminium and glass driven through the front. Daniel Libeskind added that in 2007 and the city has not stopped arguing about it. Three hours goes fast.

Across the road is a museum devoted entirely to footwear, which sounds like a joke and is not: four and a half thousand years of shoes from every continent, in a building shaped like a box with the lid ajar. Forty-five minutes.

In the afternoon go twenty minutes north to Casa Loma. Sir Henry Pellatt made a fortune electrifying Ontario, spent it between 1911 and 1914 on a ninety-eight room castle with stables reached through a tunnel under the road, lived there under a decade and lost everything. It is absurd, it knows it, and the view south from the towers takes in the whole city.

Dinner somewhere with a neighbourhood around it: College Street west of Bathurst, or the Danforth across the valley.

Breakfast at St Lawrence Market, which has been feeding this corner of the city since 1803 and from these buildings since the 1840s. Go to the south hall and order a peameal bacon sandwich, which was invented here and is not what anyone outside Canada means by bacon. Saturdays bring the farmers into the north building from five in the morning.

Then ten minutes on foot to the ferry docks. The Toronto Islands are a chain of sandbars fifteen minutes offshore with about seven hundred residents, no cars, and the only good view of the skyline, which is from a kilometre of open water rather than from inside it.

Ferries serve three points. Centre Island has the beach and a small amusement park. Ward's Island at the east end is the quiet one, a village of a couple of hundred cottages with a boardwalk running back along the lake. Take the boat to one end, walk to the other in about an hour, and come back from there.

Eat on the mainland. There is one restaurant on the islands and several hundred west of downtown.

Union Station in the morning and a bit over four hours northeast along the lake and up the Rideau. Sit on the right leaving Toronto for the water.

The station in Ottawa is on the light rail and downtown is fifteen minutes away. Leave the luggage and go straight up to Parliament Hill, which stands on a bluff over the river in high Victorian Gothic. The tower in the middle is a memorial: the original building burned down in February 1916 with the war on, and what replaced it was named the Peace Tower and finished in 1927. The Centre Block has been closed since 2019 for a restoration that will run into the 2030s, so the free tours go through the West Block, where the Commons now sits in a glazed-over courtyard. Book those online before you travel.

Then five minutes east to the ByWard Market, which has been the middle of the city since the 1820s and has moved on from taverns and brothels to produce stalls, restaurants and a very long queue for doughnuts. Eat here tonight.

The National Gallery is across the road from the market, in a glass and granite building Moshe Safdie set on the cliff in 1988, whose great hall deliberately answers the parliamentary library across the water. Louise Bourgeois's nine metre bronze spider stands outside. Inside, go to the Canadian and Indigenous galleries first: the Group of Seven, Emily Carr, and a very large contemporary Inuit and First Nations collection.

The mint is two minutes away in a small Victorian fortress and strikes Canada's collector and commemorative coins along with bullion for other countries. The circulating coins in your pocket are made in Winnipeg. The tour runs under an hour and ends with an invitation to lift a gold bar, which you will not be able to do.

In the afternoon, west along the river to the Canadian War Museum. Raymond Moriyama sank it into the ground in 2005 as a long concrete wedge under a sloping green roof, and the galleries get lower and darker as the twentieth century gets worse. Regeneration Hall at the end points a narrow window straight at the Peace Tower.

It is not a cheerful afternoon and it is the best building in the city.

A short hop today, about two hours down the Ottawa valley, arriving at Gare Centrale in the middle of the afternoon. The station is underneath the office towers and connects straight into the metro, which matters in January and is convenient in every other month.

Go down to Old Montreal for the evening. Notre-Dame is the reason. From the street it is a competent piece of Gothic Revival; inside it is deep blue, gilded, carved from walnut and lit like a stage set, which is what its designer intended, having designed sets for a living. It was finished in 1829, when it was the largest church in North America.

Then walk uphill to Place Jacques-Cartier, the sloping cobbled square in the middle of the old town, full of buskers and portrait artists and priced accordingly. Have dinner off the square and get an early night. Tomorrow involves a mountain.

The mountain first. Mount Royal is a two hundred metre lump of hard rock left in the middle of the island, and the park on it was laid out in the 1870s by Frederick Law Olmsted, fresh from Central Park, who curved the paths deliberately so that the climb feels easier than it is. From the lookout you get downtown, the river and, on a clear day, the mountains in Vermont.

Come down the eastern side into the Plateau, the part of the city people picture: three-storey terraces in brick and greystone, each flat reached by its own iron staircase spiralling up from the pavement. They exist because of a nineteenth century bylaw and a shortage of interior space, and they are lethal in an ice storm.

Lunch is smoked meat and the argument about where is one you will not settle. The place on Saint-Laurent has been curing brisket since 1928, the tables are shared, and the correct order is medium fat on rye with a pickle. Walk north through Mile End for bagels straight out of a wood oven, then carry on to Little Italy for the market, which is the largest open-air one in North America and tells you exactly what Quebec grows and when.

Dinner in a proper French bistro with a zinc bar, at about half what the same meal costs in Paris.

Two big things at opposite ends of the metro today, and the metro handles both without difficulty.

Saint Joseph's Oratory is the largest church in Canada, on the northwest flank of the mountain, and it is a strange building: a stark Art Deco interior under an enormous dome, built in stages through the first half of the twentieth century around the shrine of a lay brother believed to heal the sick. The crutches left behind by people who walked away still hang in the votive chapel. The middle flight of the outdoor stair is wooden and pilgrims climb it on their knees.

Then east to Pie-IX, where the 1976 Olympics left a stadium that took three decades to pay off and never quite worked. Its leaning tower is the tallest of its kind anywhere and a funicular runs up the outside. Next door is the botanical garden, which is much the better half of the afternoon: seventy-five hectares, with Chinese and Japanese gardens that are the real thing rather than a gesture.

Eat unrepentantly tonight. Quebec cooking at full strength is duck, pork, foie gras and maple.

Three and a quarter hours downriver, arriving at Gare du Palais, a turreted pile in the lower town that looks like a small version of the hotel on the cliff above it because the same architect did both. The old town is ten minutes uphill.

Go straight to the cliff edge. Dufferin Terrace is a wooden boardwalk along the top of the escarpment, built over the foundations of the French governors' chateau, and it is the best free thing in the city: the St Lawrence a couple of kilometres wide below you, the ferry crossing to Levis every twenty minutes, and the Chateau Frontenac standing behind. That hotel went up in 1893, built by Canadian Pacific to give people a reason to buy railway tickets, and it worked so well that it is now shorthand for the entire country.

A few minutes inland is the basilica-cathedral, seat of the oldest Catholic parish north of Mexico, founded in 1647 and rebuilt twice after fire and bombardment.

Eat properly tonight. Quebecois cooking is game, root vegetables, maple and pastry, and the tourist end of it here is much better than that sounds.

Everything today is below the cliff, and the way down is half the point. The Escalier Casse-Cou has been on this line since the 1630s and the name, the Breakneck Stairs, is not a marketing decision: cattle were driven down here to the lower town market and the gradient shows it.

At the bottom is Rue du Petit Champlain, a lane of seventeenth and eighteenth century houses that is the oldest shopping street in North America and thoroughly aware of it. At nine you have it to yourself; by two you are in a queue.

A hundred metres on is Place-Royale, the square built on the exact ground where Champlain put his habitation in 1608. It is small, stone and closed on every side, and the painted wall at the top rewards five minutes of working out who is who. The church on it went up in 1688 on the foundations of Champlain's own building, is the oldest stone church in North America, and is named for two failed sieges, which tells you how the seventeenth century went here.

Lunch in the lower town, then let the afternoon go and ride the cable railway back up the cliff for a drink as the light drops.

Finish at the top of the cliff. The Citadelle sits on the highest point of Cap Diamant in a four-pointed star, built by the British between 1820 and 1850 against an American attack that never came, on top of French works already a century old. It is a working army base, home of the Royal 22e Regiment, whose members serve in French and whose ceremonial guard wear scarlet and bearskins.

From late June to early September the changing of the guard happens at ten in the morning, which is the reason to be there early. Out of season you go round with a guide, which is better history and much less spectacle. Either way you get the view back along the wall and down the river that explains the entire town.

From the gate it is twenty minutes downhill to Gare du Palais and about the same by taxi to Jean Lesage airport, which has connections through Montreal and Toronto.