I went with a group of people affiliated with an Annapolis nonprofit organization called Upstream Alliance. The Inwood Canoe Club, on the Hudson in far northern Manhattan, kindly allowed us to store the boats overnight and launch from its docks. The Circ’s organizers had divided the fleet into three groups based on anticipated speed; two of the groups launched a few hundred yards from us at a public beach on Dyckman Street.

The Inwood is the only survivor of a string of boat clubs that once lined that part of the island’s shore. Founded in 1902, and the home of seven Olympic canoeists in the middle of the last century, it recalled an era when New York’s waterways were more recreational than they are today, and perhaps cleaner and less intimidating.

The day and hour of the Circ are chosen so that tidal flow will assist participants as much as possible. As we paddled into the eastern edge of the Hudson’s channel, it was immediately clear this would not be a trip for the inattentive. The flow was swift. The river was in full ebb, doubling our paddling speed toward the Battery, the southern tip of island, where we would catch the flood tide that would carry us up the East River.

The group I was in would, in theory, be the fastest of the three. A motor launch appeared on our right. It accompanied us the whole way around, keeping us from straying into the all-business middle of the channel, like a border collie herding a flock of aquatic sheep.

The overcast sky hid the tops of the George Washington Bridge’s towers. We paused briefly just above the bridge and then proceeded under it. A rumbling filled the air and disappeared. White, balloon-shaped buoys — presumably for transient yachts — strained against their mooring chains, the dark water pillowing over them. They were the first of several not-so-obvious obstructions we encountered that could easily have flipped a boat. (Thankfully, none did).

Things are better now. Thousands of people swam in the Hudson the day after the Circ as part of the New York City Triathlon. The Billion Oyster Project is engaging schools (among other groups) to restore New York’s oyster grounds. There were 220,000 acres when Henry Hudson navigated the waters in 1609; the project so far has restored a little more than one acre and planted 22 million oysters. Heavy rains occasionally overwhelm the wastewater treatment capacity, spilling coliform-laden water into the rivers. We got occasional whiffs of sulfurous sewer gas on our passage.

We stopped at Pier 40, at West and Houston streets, in Greenwich Village, where people looking for a bathroom could admire the watercraft in the Village Community Boathouse. It promotes the construction and rowing of dory-like boats of a century-old design called “Whitehall gigs”— one of many examples of how New Yorkers are again turning to the water for recreation.

We approached the Battery with the Statue of Liberty and Ellis Island in the distance to our right, and One World Trade Center on our left. The waterway here is New York’s aortic outflow — high-pressure, turbulent, essential. The Circ organizers arranged for us to cross it in 15-minute windows that would keep us safe from the gigantic, orange Staten Island ferry and its wake. By then, our group had caught up with the second-fastest one. We watched its paddlers cross as we milled around near a barge in a man-made cove — in this part of Manhattan, everything is man-made — waving to pedestrians on the waterside promenade.

Eventually, we got the signal to cross. This required hard, no-nonsense paddling. (I was chastised by one of our chaperons for pausing to take a picture.) At one point, we had to hold up unexpectedly to avoid a tour boat. As we headed into the East River, the water became a hectic mix of standing waves, wakes and clashing currents. Nobody appeared to be giving us much quarter. We were like mice crossing a crusty field of snow, hoping not to be picked off by predators.

Safe on the Brooklyn side, we caught our breath and headed up the East River under the Brooklyn, Manhattan and Williamsburg bridges. We passed the blackened stubs of old dock pilings, shuddering in the current like loose teeth.

We paddled the length of Roosevelt Island and at its far end came ashore at a beach in the Astoria neighborhood of Queens. We tarried there until the tide became favorable. Because the beach would flood, we carried the boats — the entire fleet, as the three groups were now together — up the street to Socrates Sculpture Park, a four-acre outdoor museum built on an old landfill. There, an overworked food truck, a small farmers market and a performance of Bengali music and dance entertained us for nearly two hours.

We crossed to the Manhattan side of the river at the lower end of Hell Gate, the most notorious strait in New York’s harbor and the site of uncountable shipwrecks over the centuries. The water was slack; our timing was right. We paddled right over the spot off East 90th Street where the excursion steamer General Slocum, carrying 1,400 people — most of them recent German immigrants — caught fire on June 15, 1904. The death toll of at least 1,021 would not be exceeded in a single disaster in New York until 9/11.

At the north end of Randalls Island, we turned left into the Harlem River, where we were favored by the tidal quirk that makes the circumnavigation such a winning proposition. The tide pushes water that is already in the Harlem River northward, as well as pushing water that is not already in the Harlem River into it. One wouldn’t think it possible! But it happens twice a day.

(Here, it’s worth noting the distance around the island was 30 miles, which we covered in 6½ hours of paddling time. Our average speed was just under 5 mph and our maximum speed an astonishing 8.7 mph. An oceanographer in our group calculated we did the work of a 20-mile paddle at 3½ mph. In other words, one third of the distance we covered was entirely thanks to tide and river flow.)

A paddler pointed out the garbage pier, the air vent for the Holland Tunnel and a row of Trump Organization-built apartment buildings recently stripped of their builder’s name. Another told me as we passed under the Queensboro Bridge that it was also known as the 59th Street Bridge. (“Are you feeling groovy yet?” he asked.) I learned about Marble Hill, the Manhattan neighborhood that is no longer on Manhattan Island, thanks to rerouting of the Harlem River at the northern end of the island in 1895.

I was instructed to note the Pepsi-Cola sign in Long Island City in Queens, a landmark that’s both pop-cultural and nostalgic-industrial. From my reading of the aforementioned Mitchell essay, I pointed out to a fellow circumnavigator that the eddies at the bend of the East River between the Manhattan and Williamsburg bridges is where corpses that go into the water in the winter frequently surface in the spring.

We paddled under more than a dozen bridges; Manhattan is an island, after all. The oldest is High Bridge, opened in 1848 to carry the Croton Aqueduct that supplied water to the city. Macombs Dam Bridge (1895), near Yankee Stadium, with its stone piers, pyramid-roofed shelter houses and steel camelback in the middle, is my new favorite.

As the Harlem River got narrower and more industrial, culminating in the ship channel of Spuyten Duyvil, I was amazed to see a rocky outcrop on my left, the very northern tip of the island. I paddled over. It was shaded by vegetation growing out of its face and vines hanging down from its top. The air was laden with the smell of moss and mold. I thought to myself: “This, at least, is unchanged. This is something the Lenape Indians and the Dutch colonists might recognize.” Then I thought about the blasting it took to make the ship channel. “Maybe not.”

The rivers the Circ followed were pretty much where they’d been in 1600. The currents and tides were the same (and so, undoubtedly, were some of the water molecules). Flowing water was the changeless New York City, and I’d been looking at it all day.

Interior walkways inside the Eastern State Penitentiary. In the travel industry, prison museums are a growth sector. (David Brown)

I was halfway down Block 1 at Eastern State Penitentiary in Philadelphia, peering into a cell for a thief imprisoned in 1829, when I realized the place resembled a Carthusian monastery.

Members of Catholicism’s most austere order, Carthusian monks live, eat, work and sleep alone in “cells,” coming out only for church services and a four-hour walk each week. They are forbidden to speak unless given permission. Each man has a tiny walled yard where he can look at the sky and feel the sun. As the wonderful book “An Infinity of Little Hours” (2006) makes clear, it’s a life balanced between sanctity and madness.

In the first era of Eastern State’s 142-year life as a prison, inmates spent 23 hours a day in their cells, with two half-hour recesses in private yards reached by a stoop-through door. Their only reading material was the Bible, and they spoke to no one but guards and the chaplain. If they left their cells, they were hooded. Some spent years inside the massive stone walls without seeing the face of another prisoner.

Today, it seems odd that this was ever viewed as a way to cure antisocial behavior. But it was. In fact, the “Pennsylvania system” was penology’s breakthrough idea, rescuing murderers, burglars, forgers and confidence men from cruel treatment by keepers and fellow miscreants. Eastern State, the idea’s embodiment, went on to be the model for 300 prisons on four continents.

Seeing how “penitence” got into the word “penitentiary” is just one revelation that awaits a visitor to Eastern State Penitentiary, surely one of the country’s more unusual museums.

In the travel industry, prison museums are a growth sector. A book published last year, “Escape to Prison:  Penal Tourism and the Pull of Punishment,” looks at 10 of the roughly 100 of them around the world. Although some (like Alcatraz, or South Africa’s Robben Island) are better known than Eastern State, few can compete with it.

“In its educational and historical narrative, it’s clearly at the top,” said Michael Welch, the Rutgers University sociologist who wrote the book. “It’s not a theme park. It’s not intended to amuse you.”

It is, in the words of Steve Buscemi, who narrates the indispensable audio guide, “a magnificent ruin.”

The architecture is Gothic Revival, with 30-foot walls of Wissahickon schist, faux battlements and two gargoyles over the entrance holding lengths of chain. Inside, the walls are flaking paint and spalling rock dust. Birds swoop in and out of broken windows. Vines and saplings have taken up residence where prisoners worked and lived.

In the Eastern State Penitentiary exercise yard, a sculptural graph shows U.S. rates of imprisonment over time. (David Brown)

One of the prison’s innovations was its hub-and-spoke design, which is still used in many prisons. Cellblocks radiate from a central rotunda, where guards kept watch. Seven blocks are open to visitors, and hundreds of cells have been left as they were when their occupants moved out in 1971, down to tipped-over stools and open drawers.

Guides are stationed around the prison and the grounds. (Several I spoke to were recent Temple University history and archaeology graduates.) They give mini-tours to parts of what was essentially a walled town forced to evolve without changing its footprint.

“Soup Alley” is a covered walkway with cafeteria counters on either side, built in 1924, when inmates started eating together. A stove with an oven door open is covered with dust near where a tarred roof has collapsed. A dining room, created by knocking down the walled yards of the nearby cells, stands empty.

Part of Cellblock 3 was converted to a hospital in 1880. A tree root snakes over the door to the operating room, added in 1910. Inside, a steel IV pole sits in a corner and a surgical lamp the size of a searchlight hangs from the ceiling. Al “Scarface” Capone, who spent time at Eastern State in 1929, had two operations there. One was a tonsillectomy; the other, unnamed, was probably a circumcision. (Capone had syphilis, and circumcision would reduce the chance he’d transmit it.)

It’s remarkable that people are allowed in such places in this era of phobias over lead paint, trip hazards and things-you-may-have-to-duck-under. The museum shows respect for the good sense of its visitors, who numbered 194,000 last year (30,000 in group tours).

The idea for a new kind of prison originated at a meeting of the Philadelphia Society for Alleviating the Miseries of Public Prisons in 1787. (Benjamin Franklin was an early member.) Inspired by Quaker ideals and Enlightenment thinking, the prison was designed to induce regret and penitence in prisoners. It was more than 30 years before the Commonwealth of Pennsylvania took the suggestion. Eastern State Penitentiary opened its gate in 1829.

The corridors and cells have vaulted ceilings that suggest an ecclesiastical setting. The single skylight in each cell was called an “eye of God.” The food was reputedly good. Pipes under the floor delivered central heat, and bucket-flush toilets connected to a sewage system. This was a time, the commentary points out, when the White House had neither of those amenities.

However, not everyone agreed that solitary confinement was the route to reformation. Charles Dickens toured the penitentiary in 1842 and wrote: “I hold this slow and daily tampering with the mysteries of the brain to be immeasurably worse than any torture of the body . . . it extorts few cries that human ears can hear; therefore I the more denounce it, as a secret punishment . . .”

The “Pennsylvania System” of solitary confinement didn’t last long. As early as the 1840s some prisoners had cellmates, and in 1913 the strategy was abandoned. New multi-tiered cellblocks were squeezed in between the original ones. By the 1920s, the institution built for 700 inmates housed 2,000.

The walls are flaking paint and spilling rock dust inside the Eastern State Penitentiary, which opened its gate in 1829. (David Brown)

 

A cell at Eastern State Penitentiary, which was designed to induce regret and penitence in prisoners. (David Brown)

The place is so big and operated for so long that the opportunities for narrative are legion. And the museum takes full advantage of them.

There are displays about women prisoners (who were there until 1923), race in prison, prison gangs and famous inmates. You can see the restored synagogue, Capone’s cell and the place from which 12 people, including the bank robber Willie Sutton, escaped (temporarily) through a tunnel. A dozen cells have been given over to artists for installations. On display now is a reconstruction of a cell from Camp X-Ray at Guantanamo Bay. Another, called “Other Absences,” has pictures of 50 men, women and one child murdered by former inmates hanging from the ceiling of two cells.

What wasn’t addressed for years, however, was the growth of imprisonment in the United States, a trend known as mass incarceration.

“There was this massive blind spot,” said Sean Kelley, the director of interpretation and public programming who was the museum’s first full-time staff member in 1995. “The old ending of the audio tour asked people to reflect on the current incarceration system. But we didn’t give them any facts on which to reflect. It was essentially the same as saying, ‘Drive safe.’ ”

Today, the facts are hard to miss. They take the form of a $100,000 sculpture erected in 2014 in the center of the exercise yard.

The corridors and cells in the Eastern State Penitentiary have vaulted ceilings that suggest an ecclesiastical setting. (David Brown/For The Washington Post)

For every decade since 1900, the number of people imprisoned in the United States per 100,000 population is depicted as a steel box of proportionate height. Through 1980 the rate varied from 100 to 200. Those boxes are a couple of feet high; you could step from one to the next if they let you. Then the rate took off. In 2010, it was 730 per 100,000, and the box is 16 feet tall. Viewed from other angles, the 3-D infographic compares the U.S. imprisonment rate with that of other countries, and it also depicts the racial breakdown of the American prison population over time.

The museum is finding other ways, as well, to engage the subject of crime and punishment.  On the first Tuesday of each month, a scholar, author or public official gives a talk in the rotunda, followed by a reception.  September’s speaker, the Philadelphia Police Commissioner Charles Ramsey, was shouted down by Black Lives Matter protesters.

Eastern State Penitentiary, too massive and obsolete to be repurposed after it closed, has found new life helping people, once again, think about the purpose of imprisonment. Its long-dead founders would be pleased.

Loch Calavie, a small lake near Scotland’s west coast where the author camped alone on a gravel beach. (David Brown/For The Washington Post)

Two ridges of heather and grass rosed up on either side of a narrow lake, like weathered hands scooping a drink of water.  The blue sky was furrowed with clouds as bright as the patches of snow on the mountains in the distance.  A gravel beach, wide enough for a few tents, etched a parenthesis in the distance.

It was my first day out on a walk across Scotland, and I’d stumbled upon one of the most beautiful camping spots I’d ever seen. As I pitched the tent and made dinner, the light fading with arctic slowness, I kept hoping somebody would arrive to share the place with me. But nobody did. It was all mine, for better or worse.

That’s how it was for much of the next 13 days. Backpacking across Scotland, if you go alone, as I did, is an exercise in beauty, solitude and expectancy.

I made this trip in May as part of an annual event called The Great Outdoors Challenge. Named for the British outdoor magazine that sponsors it and organized by a small army of volunteers, the Challenge helps about 300 people traverse the country, from west to east. The hikers (or “Challengers,” as they call themselves) don’t all take the same route, or even a few established ones. There are no equivalents of the Appalachian Trail or the Pacific Crest Trail to follow. Instead, they custom-build routes from local hiking trails, farm and forest roads, ATV tracks, military roads built in the 18th century, and drovers’ and hunters’ trails that are even older.

Everyone leaves from one of 13 designated starting places on the west coast and finishes 13 or 14 days later on the east, traditionally by wading into the North Sea. They then make their way to Montrose, a seaside town where a celebratory banquet is held in a hotel.

You have to apply, pay a small fee and convince the organizers you’re fit before you’re accepted into the Challenge. The chief advantage of participation is the advice provided by a dozen veteran hikers, who review and approve every route — more than 200 different ones this year. These experts tell you which footbridges have been washed away, what streams are too dangerous to ford after heavy rains, where the good camping spots are, what sights not to miss.

My route was about 200 miles long. Even though it took me to a B&B or hostel about every third night, I was mostly on a camping trip — and a long one. I had to carry what I needed on my back, and be prepared for anything, including snow.

There are easier ways to hike in Scotland. The Challenge is simply an extreme version of what is Scotland’s national pastime: “hillwalking.” The country’s Outdoor Access Code allows people to walk and pitch tents on both public and private land. (There are a few exceptions, such as the British royal family’s Balmoral Estate.) All a walker has to do is stay away from crop fields, animals and buildings.

I walked 10 to 17 miles a day, with each day’s uphill sections averaging about 2,000 vertical feet. It took a lot of planning and was hard enough that I took an unscheduled rest day halfway through. But the payoff was huge. There aren’t a lot of places where you can walk sea-to-sea across a country that is beautiful, exotic and English-speaking. Scotland is one.

Although many people follow a route by GPS on a handheld device for the Challenge, carrying paper maps is also strongly advised. (David Brown)

Ruins of tenants’ cottages fill the Highlands of Scotland. (David Brown)  

One advantage of all the water is that you don’t have to carry any. Wherever you are, there’s a cold, clear, drinkable stream within a hundred yards or so. Not to mention lots of lakes, such as Loch Calavie, the gem I stumbled upon the first night.

With few trees and no jagged mountains, the Highlands are hard to get lost in. Of course, it’s different if you’re in fog or a snowstorm, but luckily the weather was clear for most of my time there. The first four days I walked down valleys and over ridges, scattering sheep, rabbits and grouse, and seeing almost no one.

The emptiness lent sweetness to the moments when a person did appear on the path, offering a few minutes of conversation, an exchange of gorp or hard candy and, occasionally, hours of companionship. Hillwalking creates a fraternity even for solo walkers (which 140 of the 298 participants this year were). That, in turn, gives Challengers permission to inquire about a fellow walker’s life, and to synopsize their own.

If you don’t want company, you can just walk on, no excuses necessary. But if you do, the Challenge can become a Canterbury Tales of interesting characters and encounters.

I walked through a rare patch of forest in the drizzle with a 75-year-old retired surgeon — a woman — whose career had been solo gigs on Hebridean islands and other far-flung spots, filling in for doctors needing a break. I spent a morning with a woman my age — 60s — who told me about growing up in postwar England, where margarine and marmalade were rationed and her house had an outdoor privy. Nothing, however, epitomized trail society better than my day with Stevie, a 56-year-old paving contractor from a town south of Glasgow.

His father had been a bus driver, he told me, and his father’s father, too. He learned to love the outdoors when the family would rent a cottage in the mountains for two weeks in the summer and he would run around with his shoes off. From an aunt, he said, “I learned to love wild birds.” He described some he’d seen in the last few days, including the once-endangered red kite. He was married once (“it wasn’t for me”) and has no children (“my one slight regret”).

When he was young, he walked with his brother and a cousin. Often it was nothing more than “a rush to get to the next town and the next bar.” As he got older he went alone, often with only a rough idea of a route. A few days before we met, he’d gone over four 3,000-foot summits in a day, stumbling into his tent after dark with just enough energy to make tea before falling asleep.

Recently, however, he’d started enjoying the company of others. He’d walked with two Germans for a day early in the Challenge. When we got to Aviemore, our mutual destination for the day, he hoped to rendezvous with a woman he’d met on the walk the previous year. “I’m learning new habits,” he said with surprise in his voice.

Nevertheless, when he wanted to go on, he did. No waiting for the American with the obese pack.

By midafternoon I figured I’d seen the last of him until I got to a long abandoned stone cottage called the Red Bothy. In the lee of the building he was having a lie-down with his boots off. We chatted briefly until I said I had to get more miles behind me. He nodded understandingly: “You go’ qui’ a big ki’.” Quite a big kit— yes, that would describe it.

He caught up to me an hour later where the road went over a divide into the watershed of the snowy Cairngorm Mountains. We sat on stone pylons in the sun and looked back at a hill we’d come over separately in the morning. It seemed an impossible distance away.

“I like being in the moment,” Stevie said, getting suddenly philosophical. “But it’s on reflection that it’s frigging brilliant. In a few weeks you forget the pain and remember only the beautiful days. And this might be one of them.”

I couldn’t have agreed more.

We got up and walked, but this time he didn’t go ahead. We descended into Aviemore together and then went our separate ways.

I saw Stevie three days later in Ballater, my next village port-of-call. He and the woman he’d been hoping to meet were in a pub near my hostel, and he greeted me like an old friend. Which, in the strange time-dilation of the trail, I was.