On Walking the Roundabout

One thing that seems to surprise everyone I speak to about my long urban hikes is that I do them solo. I suppose, for me, that the solitude is one of the largest appeals of doing something like this. There's no one else to talk me through moments of challenge, through the pain that inevitably builds when pushing your body to extreme lengths. There's only me, step after step after step, mile after mile after mile.

I've realized, here in my 40s, that my own self-doubt has been my biggest enemy and obstacle in life. Endurance workouts, like these hikes, give me a chance to meet my enemy out in the field, so to speak. After letting self-doubt claim too many victories in my first 4 decades, I absolutely refuse to let him get another.

But above all else, my motivation for urban hikes is that I love San Francisco, and there is no better, more intimate way to get to know it than to walk it. On every single walk, on paths familiar or unfamiliar, I discover new things- about The City, and about myself.

I get out of the door at 8:25am, a little later than I hoped. The first 6 miles- from home to Fisherman's Wharf, down the Embarcadero, past the Ballpark and Chase Center- are the easiest of the day. The route is flat and the path is incessantly beautiful, stuffed with iconic landmarks, and constant gorgeous views, of The Bay on one side and the downtown skyline on the other. For most, this is San Francisco at its finest.

I'm first tempted to stop as I pass by The Ramp, one of The City's most unique dives. Built in 1950 as a bait shop, it's now a no-frills bar and restaurant best known for Bloody Marys. It's a quintessential San Francisco experience, best enjoyed with a lack of expectations- it's just a good place to eat and drink, with Bay views, an ocean of outdoor seating, and a 'locals only' vibe. Alas, my feet choose momentum over mojito, and I carry on.

Speaking of vibes, they shift rapidly as I enter into what are, for the most part, the ruins of San Francisco's once thriving industrial South. Just a couple of blocks past The Ramp, the path passes Crane Cove Park, and turning a corner, I'm face to face with the Union Iron Works building. Founded as a simple blacksmith shop in 1849, Union Iron Works would grow into one of the United States' most important companies, eventually merging with Bethlehem Steel and becoming the leading Western shipbuilder for the US Navy, as well as contributing to the construction of both the Golden Gate Bridge and the Empire State Building.

It established the Southeast waterfront as an industrial powerhouse, helping usher in The City's longest boom, which saw San Francisco become the Western center of American power- militarily, economically, and culturally- all the way from the mid 1850s until past the end of World War II. But amassing all of that urban power came at a cost, one that, in some ways, would be paid by generations not yet born.

As I finish mile 9, in Hunter's Point, former home of the Naval Shipyard and current home one of the USA's largest & most polluted superfund sites, I look through a fence covered in warnings about hazardous materials and see, in the distance, the glittering spires of downtown & SOMA. These skyscrapers are now mostly inhabited by the scions of San Francisco's more recent boom industry- tech. If my feet know the mileage intimately, standing here, in my heart the distance from Hunter's Point to the Salesforce Tower feels like an ocean.

Far removed from SF's commercial and residential palaces, Hunter's Point is a neighborhood whose scars are easy to see. Thousands of units of housing have already been built in the long-running Hunters Point Shipyard redevelopment plan, in spite of the fact that radioactive materials continue to be found year after year. These materials are present owing to the shipyard becoming, starting in the late 1940s, the US Navy's main site for decommissioning ships used in atomic weapons testing.

In January 2024, the Navy finally acknowledged that, due to rising sea levels, radioactively toxic groundwater could surface at the site in less than a decade. Nevertheless, construction continues, with some of San Francisco's poorest residents inhabiting these units. 

Passing 12 miles, I turn left on Carroll Avenue and enter another home of a seemingly endless redevelopment project, Candlestick Point. Instead of heading immediately to the recreation area along the shoreline, I choose to walk a few blocks to Gilman Ave, to spend some time along the perimeter of the ruins of Candlestick Park, still the dominant feature of the neighborhood, and former home of both the Giants and 49ers. The irony is not lost on me later in the night when, almost at the end of the hike, passing a bar in Fisherman's Wharf, I see that like their former home, the 49ers season has also come to ruin, with a 41-6 loss in Seattle.

Out on the end of Candlestick Point, as I hit 14 miles, I take a few minutes to relace my shoes and pop a couple of ibuprofen. This is mostly preventative at this point- I'm starting to feel the mileage in my hips and feet a bit, but I'm still feeling pretty good.

The southern end of Candlestick Point is, sadly, marred by civic neglect. There's some lovely landscape down here, but I'd been on this same stretch on my 27-miler, and the same piles of rotting trash and photo-decaying plastic were still here 3 weeks later. City services seem to have abandoned Candlestick, just as the 49ers did a decade prior.

Hitting 15 miles, I chug a protein shake and pass under the 101, entering Little Hollywood, the first of several neighborhoods strung together in this section of the hike- Visitacion Valley, Bayshore, Crocker-Amazon, the Outer Mission, the Excelsior, Ocean View. The Visitacion Valley Greenway is a gem here, a chain of 6 mid-block public gardens and park spaces. The Crosstown Trail takes you up elevation through the North half of the Greenway, over the top of McLaren Park, while The Roundabout has you descend into Bayshore past the Cow Palace.

As I wind out towards Lake Merced through the neighborhoods, Cayuga Park is my favorite find of the day. A serene oasis in spite of being in the shadow of I-280, it is filled with several hundred totems, sculptures, statues, and other pieces of art,. A wide range of styles, materials, and techniques are on display here, and so I was surprised to learn that they are all the work of Demetrio Braceros, a Filipino immigrant who worked for SF Parks and Rec as a gardener, was assigned to Cayuga Park in 1986, and then spent over two decades more than living up to his directive to "change the atmosphere" of the once sparse and forgotten park. 

3 years after his retirement in 2008, Braceros' efforts to revitalize Cayuga Park led to it getting a full 9.4 million dollar renovation, complete with a 2500 square foot clubhouse, basketball courts, and a top class children's playground. It all stands as a living testament to the very real fact that a single person, by taking small actions every day over a long stretch of time, can change the world they inhabit. 

Around mile 22, I pop two more Ibuprofen. My legs and feet are starting to let me know they don't appreciate what's happening. The path dips into Daly City, past the BART station, through a disorienting few hundred feet underground in the pedestrian tunnel which passes again under I-280.  I approach Lake Merced and, ever so briefly, pass through Broderick Terry Duel Landmark Park.

It's modern existence, as what appears to be a quiet, de facto dog park, belies the grim history memorialized here. In 1859, it was the site of the last known duel, fought between U.S. Senator from California, David C. Broderick, and former California Supreme Court Justice, David S. Terry. Once friends, their friendship soured over slavery. Both Democrats, Senator Broderick led the abolitionist wing of the party in the state, and when the anti-abolition Terry failed to win re-election to his seat, he blamed Broderick. A series of escalating accusations and insults led to Terry demanding the duel, which took place on September 13, 1859.

Broderick was wounded in the duel, and succumbed three days later, on September 16. Before dying, he said "They have killed me because I was opposed to slavery and a corrupt administration." Broderick became a martyr for the abolitionist movement, and his death led to public outrage, as well as the widespread condemnation of the practice of dueling. Laws banning it passed first in California, and then nationwide. 

Around Lake Merced, and up into Fort Funston, passing the 25 mile mark, I crest a hill and catch sight of the Pacific Ocean. Today, it's more beautiful to me than it's ever been, a respite after 12 miles winding through the various neighborhoods along the Southern edge of The City. While the sight is breathtaking, the trail makers chose to thread The Roundabout through Fort Funston's sand dunes, and 25+ miles in, this is a hard mile to get to the Great Highway. The journey takes a transition here- every step I take from the dunes until the end of the day will be a step through pain. As I reach the Great Highway, it's taken me 7 hours to cover the first 26 miles. It will take 5 to cover the last 14, as my pace starts to slow.

When looking at the route, I'd originally expected the 4 miles up the Great Highway would be among the most difficult of the day- once fatigue and pain hit, long stretches like this can become a test of will. But on this day, miles 26-30 are like the eye of the storm, a welcome calm between the dunes, and a test that I hadn't anticipated that is still to come. It feels like the entire city is out walking, running, biking, skateboarding, or just generally playing at Sunset Dunes, San Francisco's newest major park, and a popular one at that. Nevertheless, it's formation cost District 4 Supervisor Joel Engardio his job. 

Our recall system is broken, and it has been exploited a number of times in recent years- Engardio was just the latest victim. The same broken process claimed the career of San Francisco's District Attorney Chesa Boudin in 2022. Signature gathering for Boudin's recall literally began before he was sworn into office, and was accompanied by a relentless smear campaign without a basis in reality. 

I thought about Chesa as I watched the Cliff House slowly grow larger as I walked the 4 miles up the Great Highway. We ran into him there in late 2022, a few months after his recall. He was kind, gracious, and thanked me for having been a supporter, but he wore a heavy sadness. It was easy to understand, but even now, difficult to accept.

The sun is sinking as I hit Land's End and the Sutro Bath ruins. At the opposite corner of San Francisco from the ruins at Candlestick Point, both directionally and spiritually, Land's End is bustling, full of tourists and locals. 

Rightly so! This is one of the most breathtaking vistas in the world- a mixture of the natural and man-made and a reminder of the impermanence of both, teetering on the edge of oblivion, overlooking the chaotic waves of the Pacific as they crash into the Golden Gate. I've been here many times, but every visit still evokes the same sense of wonder.

 I linger to take some photos, perhaps too long given the impending dusk, and then make my way through Land's End, towards The Presidio, as night begins to fall. Light disappears quickly out here. The next two miles will be the most punishing of the day.

My old enemy, self-doubt, finally asserts himself as I struggle to navigate the Presidio trails. Every step hurts, and out there in the darkness, I hear a whispering voice telling me to give up, to sit down, to surrender. I tell myself "I'M THAT M- F-" and step on. Two floodlights at the top of the cliff give me just enough light to see the path for a few minutes. I have no idea what they're attached to, but I'm glad they're up there.

I take a wrong turn, which leads me into Battery Crosby instead of around it. When I reach the end of this route, walled off by concrete, I'm too exhausted to backtrack. I find stone stairs that take me most of the way to the top of the inside of the enclosure, hoist myself up the rest of the way over the wall, and slide down the Battery's sloped front side to put me back on the right path. I take a minute to catch my breath and soldier on.

Through Crissy Field, the path leads up to Tunnel Top Park- a gorgeous vista in the daytime. "Will the food trucks still be there?", I ask myself as I ascend. They will not, but I make it to Il Parco just a few minutes before it closes, and get a to-go Aperol Spritz. 

After going back to the path, I take my final detour of the day so that I can walk through, and then around, The Palace of Fine Arts. This is one of my favorite places in San Francisco, and it holds a special meaning for me personally, as it's where I proposed to my wife back in 2013.

I consider skipping Fort Mason after my experience in The Presidio, but as I've walked these paths many times in the daytime, I trust myself to find the right way, and I do. Past Aquatic Cove, for the last time in the day I'm tempted to stop, this time at the newly opened Taco Bell Cantina in Fisherman's Wharf, but I know that home is what I really crave. Every block of the last mile feels like an eon, but as I round the final corner, I'm awash in emotions. The biggest is gratitude- for my life, for my health, for my family, and for The City I've just outlined with my feet. I walk in my front door a few minutes after 8:30pm. I've taken 82,000 steps in just over 12 hours, clocking 40.1 miles.