Story & Photographs by Chuck Haney

With “Rice-A-Roni, the San Francisco Treat,” the catchy jingle from the 1960s, reverberating in my head, I pierced through the low-hanging fog bank as I pedaled across the iconic Golden Gate Bridge for the very first time almost 10 years ago. Perhaps fog-induced delirium or the giddiness of doing something I had not done before made quirky music bounce around in my brain. Whatever. I was experiencing both the bridge and the city of San Francisco in a whole new way: on two wheels.

I’ve been a regular visitor to San Francisco for nearly a decade. I find the city interesting on so many levels that I keep coming back. The history, the architecture, the views, the steep hills, the amazing array of food, and the city’s attraction of free thinkers all continually entice me. In the ’50s, there was the Beat culture; in the ’60s, the city was the epicenter of counterculture; in the ’70s, it was home to the gay liberation movement; and now the tech revolution continually shapes views and brings a certain fresh, positive vibe that I feel when I’m exploring the city. I photograph San Francisco with zeal and crave my next visit.

When in San Francisco, I walk — a lot. It’s the best way to get to know a city and its neighborhoods. During past walking jaunts, I couldn’t help but notice the many cyclists weaving their way around the city’s busy arteries. I also noticed many green numbered bicycle routes and bike-lane signage prominently displayed on traffic posts along many of my favorite streets.

The city, only 47 square miles, is packed with over 800,000 residents, plus thousands of tourists. I have attentively watched the savvy bicycling commuters each morning, but for my first trip on two wheels I decided to download the San Francisco bicycle route map to best get to know my way around the city while safely following a relatively flat route.

Usually I prefer the road less traveled. After all, I grew up in a rural farming community in Ohio and now live in the relatively remote northwestern corner of Montana where riding many miles on lonely country roads is the norm. I am not in the least accustomed to urban riding. Initially, city riding did not look all that appealing. All that “stop and go” and all those automobiles were intimidating enough for me to say, “I’d rather walk.” But it turned out I was wrong. 

Cycling in San Francisco can be a most rewarding experience with proper route planning. The city contains legendary slopes that can bring the strongest of cyclists to his or her knees. You certainly don’t want to go into it blindly and start heading up a 25-percent steep grade. Quickly you and your bike would be going backwards before going forwards. There are 25 streets in the city that boast over a 25-percent incline. Bradford Street in the Bernal Heights neighborhood is an astounding 41-percent grade — that’s a severe pitch for even a downhill skier!

Being the avid cyclist that I am, bringing my own road bike, or renting one, is part of the fabric of all my trips. On my most recent trip, I rented a nice, lightweight carbon Trek from a local bike shop near where I stayed in a neighborhood called Cow Hollow. For a shakedown ride, I took a series of side streets to the Presidio, a former military outpost and now part of the Golden Gate National Recreation Area. I passed the entrance sign that stated it had been a Spanish garrison in 1776. The concrete jungle of the city was soon replaced by a most pleasant stretch of pavement in a forested setting of Monterey cypress and eucalyptus trees punctuated by well-kept historic military buildings. I rolled past the San Francisco National Cemetery, a green hill dotted with 30,000 white headstones of military veterans and their families. Fittingly, their final resting spot has a commanding view of the Golden Gate Bridge. I descended to San Francisco Bay and the foot of the massive orange bridge, pausing to take in the spectacle of one of the world’s man-made wonders before turning back and riding on a bike path past marinas full of sailboats and green fields with people out enjoying a sunny day. I hopped over and found smooth dedicated bike lanes on Francisco and Polk streets that whisked me back to my hotel. Maybe this city riding wasn’t so bad after all.

My research told me that the famed Paradise Drive ride was not to be missed. I got a nice early start from my hotel near Russian Hill on a Saturday morning blessed with calm winds and abundant sunshine. Traveling from Polk Street to Francisco to Marina all on dedicated bike lanes was a stress-free city ride for this country boy. The Golden Gate Bridge’s vermilion glistened in the morning sun like a siren song beckoning me onward. Soon, other Lycra-clad riders converged from other routes, and by the time I reached the bridge I had joined a steady and colorful stream of cyclists heading north across the bay. It felt like old times on a large organized ride like the Tour of the Scioto River Valley (TOSRV) back in Ohio. Here, on weekends, cyclists have the entire westward sidewalk to themselves with walkers relegated to the east sidewalk. I had ridden across the bridge several times before, but the thrill remained the same when pedaling 220 feet above the bay.

Upon arriving at the Marin Headlands, it was a swift descent to the water’s edge. I passed a policeman lurking on a pullout about halfway down the descent and wondered whether it was a speed trap for cyclists. I cruised by the nicely manicured grounds of Fort Baker. The next few miles rolling into Sausalito were as good as it gets, with no automobile traffic, no wind, and an amazing view of the Golden Gate Bridge and San Francisco behind me. The waterfront coffee shops looked mighty tempting, but I continued north and was soon on the Mill Valley–Sausalito bicycle path along Bothin Marsh Preserve. Then things got tricky. A day earlier, Justin at City Cycle had given me a few tips on avoiding busier stretches of roadway, so I took a hard right at the Tiburon Highway intersection as he’d suggested but then rode up a steady hill only to find a dead end! Not wanting to wander off course too badly, I backtracked and rode the shoulder of Tiburon Boulevard Highway 131, which wasn’t busy with traffic early in the morning. Soon enough, I exited the highway and pedaled along another dedicated multi-use pathway with Richardson Bay, Angel Island, and San Francisco serving as a stunning backdrop to my right. After reaching the lovely small burg of Tiburon, the real cycling fun began. I was now spinning the rolling hills of the famed Paradise Drive. The pavement was living up to its glorified reputation right from the start, with one curve leading into another and only other cyclists whipping by in the opposite direction. The Richmond–San Rafael Bridge was steady in the distance along with notorious San Quentin, California’s oldest prison. Riding Paradise Drive was really cycling nirvana, and it only got better by the mile as the road was ultra smooth due to a recent resurfacing project.

The euphoria of Paradise had to end sometime though, and soon I found myself riding back in the town of Corte Madera with its bustle. I pulled out the map that I had gotten at the shop to make sure I was still on the right track; there had been quite a few turns and route adjustments on this section of the loop. I asked another rider whether he was headed in the same direction, and he said to follow him. We rode together through the town and then began a long climb. Again I deferred to advice I had received about a better option than the main route, so I veered off at the summit of the climb onto tight and twisty Chapman Drive, thinking about how smart I was for a first-timer. Perhaps even the locals didn’t know about this fun shortcut that avoided a busier road. My brief bubble burst when I reached the bottom and discovered that I was right back where I had started! Although I had been in paradise just a few miles ago, I was now lost and confused in Corte Madera! 

I really didn’t know which direction to head next so I backtracked and asked several riders if I could tag along (again) back to Sausalito. One of the guys said he knew of a better way back. You guessed it — Chapman Drive. Only we would be climbing it instead of descending. I discovered my blunder — I had gone down when I should have gone up. Oh well, a few extra miles on such a gorgeous Saturday morning were a bonus. As there was a steady string of cyclists, I made conversation with another fellow, Eric, who piqued my interest with his bright yellow, vintage steel-framed steed. Riding with Eric ensured that I did not make any more navigational mistakes as we headed back into Sausalito.

Coming back into the city, my peaceful 8:00 am ride was replaced by the sheer mayhem of a steady collection of every type of rider imaginable. Renting a cheap bike to ride across the Golden Gate Bridge is a very popular tourist activity. “Blazing Saddles” rentals must start by 10:00 am because their hybrid bikes were easy to spot with their colorful handlebar bags. The extent of wobbling riders along the narrow path of the Golden Gate indicated that most had not ridden a bicycle in many years. The “deer in the headlights” syndrome was a dead giveaway of adrenaline, terror, or just inexperience. It was not comforting to be riding directly into this steady line of chaos! I was relieved to come out unscathed as I reached city ground again.

Reflecting back, I can see why the Paradise Loop is so highly regarded by local cyclists. It is in my Top 10 favorite rides now.

Another great ride, once you get across the bridge to the Marin Headlands, is a shorter option but just as scenic. Head left up the hill on Conzelman Road. I have always been amazed at the steady stream of headlights from dedicated road cyclists climbing up the scenic route at dawn. The road is famous for its tremendous views from the Marin Headlands back to the Golden Gate Bridge and San Francisco. Every pedal stroke on the ultra-smooth pavement (with a marked bike shoulder) revealed a unique view. Once cresting Hawk Hill, however, it’s all business and concentration — the start of the descent to Point Bonita Lighthouse is a doozy rivaling any amusement park ride for its adrenaline rush. There are great options from this juncture at Bunker Road: you can head back to the bridge and the city or extend the ride further into Sausalito or Mill Valley, where the ascent to Mount Tamalpais is popular. There is a great waterproof map available through the Marin County Bicycle Coalition and designed by local mountain bike legend Joe Breeze. 

Next, I decided to sample some of the riding opportunities south of San Francisco as I had always wanted to cycle on the famed California Highway 1 along the rugged beauty of the Pacific coastline. I began in the quaint beach town of Half Moon Bay early on a weekend, and I was soon joined by bands of other cyclists also heading south. There was an ample shoulder to ride the hilly terrain, which revealed a distinct look at the coast at each bend in the road. I easily succumbed to the temptation to stop and take in some of the remote stretches of beach. Sometimes it’s nice not to be in a hurry on the bike! Walking among the dramatic cliffs at Pomponi State Beach was very soothing for the soul. I strayed off course from my out-and-back route just long enough to make a great discovery: there were excellent roads inland with much less traffic. I needed to explore. As much as I like an ocean view, I love a lonely winding road through lush green hills even more.

After picking up a few maps and doing a little research, I was back to explore the remote roads of San Mateo County. These inland rides would be more like the rural riding that I was accustomed to. I parked my car in the tiny town of Pescadero and proceeded north along Stage Road. Within a few pedal strokes, I was cruising farm and ranch country where scattered bands of cattle grazed, their black forms contrasting against the green hills. A pair of mule deer bounded in graceful unison beside me. There is often fog or low-hanging clouds in this area, but on this particular day there was nary a cloud to be seen. The narrow road buffeted me from the blustery winds whipping off the ocean yet still yielded amazing distant views of the blue Pacific. 

I was still getting my ocean views but without mechanized companions. I descended into San Gregorio, which is home only to a small general store and an old stagecoach post. I visited with a local cyclist who was awaiting his riding companions for their morning ride. He told me I shouldn’t miss the amazing locally grown artichokes and the creamy artichoke soup at the historic Duarte’s Restaurant back in Pescadero.

Then I was off on Highway 84 to the small village of La Honda where I encountered small packs of riders coming in the opposite direction from Silicon Valley. I turned off onto Pescadero Creek Road and began climbing into the Santa Cruz Mountains. As I gained elevation, the landscape changed from Monterey cypress and eucalyptus trees to a majestic redwood forest. I took in a lot of sweet oxygen as the earthy scent of being in the midst of giant trees gave me inspiration, and I reveled in the moment. The payoff for all of the climbing was a fast descent on smooth pavement featuring big sweeping corners that reduced stately redwoods into blurs of red. Nearing 30 miles, I re-entered Pescadero to complete the loop. A bowl of artichoke soup sounded mighty good for lunch.

If you would like to ride a longer version of this loop, continue north from San Gregorio on Highway 1 and climb the fabled Tunitas Creek Road; then intersect Skyline Boulevard and Kings Mountain Road and ride back to La Honda on Highway 84 for about double the mileage and climbing. You can also add to the loop that I described by continuing from Pescadero back down to the coast and Highway 1, then head south passing picturesque Pigeon Point Lighthouse and turn back inland at Gazos Creek Road. Finally, veer north on Cloverdale Road back into Pescadero. All of these rides are great options worth exploring while in the San Francisco area.  

Chuck Haney is an avid cyclist and photographer who lives in Whitefish, Montana. You can learn more about him at chuckhaney.com.