Walking San Francisco

PARKING: Off-street parking is available on Vallejo St., between Stockton and Powell Sts., opposite the police station. Curbside parking is very difficult to find and limited to 2 hours Monday–Saturday.

On most days Telegraph Hill feels like San Francisco’s Shangri-la, its wooden stairways zigzagging up hills too steep for paved streets. Walkers are naturally drawn to the steps, which weave through dense gardens and past Victorian houses both humble and refined. This little refuge tells us the rest of San Francisco hasn’t taken full advantage of its spectacularly impractical topography. Telegraph Hill wasn’t always so pretty a spot, however. Its east face was once a rock quarry overlooking a fleet of rotting ships. By the early 20th century, the hillside had become a de facto dumping ground. Beginning in the 1950s, the hill’s bohemian inhabitants transformed their hidden quarter, mostly through tasteful and imaginative landscaping.

The neighborhood is fairly luxe now, thanks to escalating real estate values, but it continues to offer the city’s best walking. A good time to walk this one is on a lightly overcast morning, when details are drawn out from the shadows beneath the trees.

Walk Description

The hill slopes up from North Beach, so we’ll start at Washington Square, on the corner of Filbert and Stockton. You’ll likely notice the long lines snaking down the street for

Mama’s on Washington, one of the city’s most sought-after brunch spots thanks to its fluffy omelets and fresh-baked pastries. Mama’s also sells to-go items if you need something to fuel you up the hill. Owner Frances “Mama” Sanchez died in 2000, but her family is keeping the delicious tradition alive and well.

Head north one block over to Greenwich. Just before you reach Greenwich, the Swiss chalet at 1736 Stockton is the

Maybeck Building, said to be the sole Arts and Crafts–style building in North Beach. Berkeley-based Bernard Maybeck, one of California’s most influential architects, designed it in 1907; it was originally the Telegraph Hill Neighborhood House, which offered services to immigrant families. Enter into a shady courtyard, which is a pleasant composition with a brick patio surrounded by varying inner faces of the building.

At Greenwich Street, turn right and head up (and up and up). At Grant, turn right and half a block down, at Gerte Alley, you’ll get an attractive preview of

Coit Tower. It’s a more-than-adequate excuse for breaking up the upward trek. Back on Greenwich head up the steps through Pimentell Garden, named for Samantha Pimentell, who tended the flora here for 25 years. The steps lead to Telegraph Hill Boulevard, on which cars spiral up to the summit. Rather than follow the road, look on the other side for the stone steps that lead to the top.

Pioneer Park, on the leveled summit of Telegraph Hill, is where you’ll find Coit Tower and a statue of Christopher Columbus, which was a gift from Columbus’s hometown of Genoa, Italy. The explorer, who for better or worse got so many things rolling in the Americas, never laid eyes on San Francisco Bay, but this bronze likeness appears to be admiring the view of it. You should do the same. The vantage here is as wide as it gets, ranging from the Golden Gate to the west and on past Treasure Island to the east. In the early days of San Francisco, the arrival of ships entering the Golden Gate was observed from this lookout, and through semaphore signals, the news, along with the type of ship, was “telegraphed” to the bustling downtown clustered on Yerba Buena Cove. Touts would sail or row out to meet the ships as they slowly proceeded into the bay. The city’s economy revolved around shipping, and the bulk of the population would rush to the docks to greet each ship as it tied in.

Coit Tower, visible from just about anywhere to the east of Nob and Russian Hills, is one of the city’s more puzzling architectural monuments. A fluted column topped by an arched observatory, it was originally derided by locals, who saw it as a sore thumb. San Franciscans are notoriously negative when it comes to new structures invading their skyline, but the city eventually came around to accepting this one. It looks particularly attractive at night, when it’s illuminated by lamps beaming up from the ground. It bears the name of Lillie Hitchcock Coit, who funded the project through an endowment specified in her will. Coit (1843–1929) was raised in San Francisco and became a big fan of a company of volunteer firefighters called Knickerbocker Engine Company No. 5. In those days, multiple companies would respond to fire alarms, and it was a competition to see which company arrived at a scene first to put out the fire. Some citizens, such as young Lillie, cheered on their favorite companies much as sports fans cheer on their favorite teams. Coit’s passion for Knickerbocker No. 5 far surpassed the norm, however, and by the age of 20 she had become an honorary member of the company. She considered it a point of honor to appear at every fire along with her beloved crew of smoke eaters. Consequently, many have speculated that Coit Tower was designed to resemble a firehose nozzle, but architect Henry T. Howard always maintained this was not his intention.

You can enter Coit Tower free of charge and circle the lobby to inspect the beautiful Works Progress Administration murals, which were added a year after the tower’s completion in 1933. These frescoes sparked a huge controversy, as some have socialist undertones and depict laborers struggling to keep up with the demands of industry. Some of the more overt details in the original works were censored before the murals were unveiled. The fresco technique is one that requires a lot of training; the plaster absorbs the paint so that it becomes part of the wall. When the frescoes were being constructed, more than 30 artists were working at once, grinding minerals for pigment and using careful application techniques. Access to the observation deck and second-floor murals costs $8 for nonresidents. On a clear day, the view from the deck is astounding and highly recommended for a 360-degree view of bridges, Alcatraz Island, and the hills of San Francisco.

Backstory: An Explosive Disagreement Among Neighbors

For many years, rock was blasted out of Telegraph Hill’s eastern side by a company called Gray Brothers. Using dynamite, the company regularly shook the foundations of the workingmen’s cottages above, and in some instances the blasts actually toppled homes into the quarry. Property on the hill, though very central, was affordable to dock hands because the grades were too steep to attract the wealthy. Gray Brothers intended to continue quarrying until Telegraph Hill was completely flattened, along the way buying out neighbors upset by the disturbance of daily blasts. Once the hill was flattened, real estate values would naturally increase, and the company could then sell the land for top dollar.

Gray Brothers used dirty tactics such as timing its blasts with Fourth of July fireworks, a fact not lost on local newspapers that described the fury this brought on, with residents “swarming to the verge of the cliff between Vallejo and Sansome Streets, with stones and brickbats and even pistols in their hands.” Indeed, Telegraph Hill residents fought back, getting a court injunction to stop the blasting, and when Gray Brothers defied the court, the neighbors rolled rocks down on the company to slow their progress. Unrelenting cheats and notorious bribers, Gray Brothers was sued more than 50 times by everyone from grocery suppliers to explosives manufacturers. Eventually karma caught up with the brothers, and one of them was killed by a company employee over unpaid wages, putting a stop to rock quarrying on Telegraph Hill. Despite the cold-blooded murder, the perpetrator was let off for reasons of temporary insanity, and no one seemed to argue that justice wasn’t served.

Exit the tower, descend the front steps, turn right, and look for the street sign for Greenwich Street. This leads not to a paved road but to some brick steps. Follow these down through dense greenery all the way to Montgomery Street. Turn left at the bottom of the stairs, and you’ll reach

Julius’ Castle, one of the hill’s kookier structures. This turreted fortress was the dreamchild of restaurateur Julius Roz, who opened the establishment in 1922. It closed in 2009 after operating for nearly nine decades and welcoming such high-profile diners as Ginger Rogers, Cary Grant, and Robert Redford. Neighborhood resident Paul Scott purchased the building in 2012 and has received permission to reopen it as a restaurant (it still hasn’t yet as of press time), so with any luck the castle will reign supreme over the hill once again.

From the castle, walk along the east (lower) side of Montgomery past two buildings, and find steps cutting back and then down Greenwich Street, a pretty darn peaceful hideaway. These gardens here are the main attraction for the neighborhood’s flock of parrots, who you’ll often hear squawking in the canopy overhead. At 231 Greenwich you’ll see some wooden steps to the right. Head up a little ways for an up-close look at some rusticated shacks that reflect the old neighborhood’s bohemian past, and then return to the Greenwich Steps and head down to the bottom. At Sansome Street, turn right and walk one block to Filbert Street.

From the bottom of Filbert, it should be instantly obvious that you have your work cut out for you. A concrete-and-metal stairway ascends a sheer cliff carved out by rock quarrying in the 19th century. Flowers cling to the cliffside, thanks to adventurous gardeners who rappelled down to plant seedlings.

From the top of the cliff rustic wooden steps lead into the

Grace Marchant Gardens, which are the most elaborate and lovingly tended gardens on the hill. Grace Marchant, a retired Hollywood stuntwoman, resided at the corner of Filbert and Napier Lane, where in 1950 she began planting the gardens that now flourish here. Her daughter, Valletta, took on a similar mission on Greenwich Street. Today, the gardens are tended by neighborhood volunteers. The land itself belongs to the city.

A wood-plank walkway leads down narrow Napier Lane, where we ought to make a short detour, for this is surely the sweetest cul de sac in all San Francisco. Little more than a footpath, it accesses a row of small houses shaded by trees. Farther up Filbert, Darrell Place is a similarly narrow, though paved, lane.

At the top of the block, the Art Deco

Malloch Building at 1360 Montgomery appeared in the 1947 film noir classic Dark Passage, starring Humphrey Bogart and Lauren Bacall; the building housed Bacall’s apartment in the film, where she allowed the fugitive Bogart to hide out. Scenes in the neighborhood reveal that the steps weren’t nearly so beautiful then as they are today. The silver nautical motifs on the building’s side make it instantly recognizable, and its streamlined Moderne style is reflected by curves both inside and out. In impeccable shape, it even retains its original elevator with a backlit glass brick shaft.

Turn left onto Montgomery and left again half a block later, onto historic Alta Street. On the south side of the block, the redbrick house with upstairs galleries at 31 Alta was a speakeasy during Prohibition. On the north side, the house at 60–64 Alta is known as the Duck House for the ducks painted beneath the eaves. Author Armistead Maupin lived in one of the building’s apartments in the early 1970s; actor Rock Hudson, a friend of Maupin’s, used to visit him here.

Backstory: Parrots Gone Wild

The parrots you’re likely to see on Telegraph Hill are cherry-headed conures, which first appeared here in the late 1970s or early 1980s with green bodies and bright red heads. Research seems to suggest that a romantic duo (parrots are monogamous for life) likely escaped from a pet shop. Or perhaps they were released; conures are known for being quite vocal about their unhappiness at being caged, and incessant squawking isn’t so good for business. Once free, they went in search of fruits, flowers, and leaves and made their way to the lush gardens of Telegraph Hill. The colorful birds now number in the hundreds among multiple flocks and fly all over the city. Mark Bittner, author of The Wild Parrots of Telegraph Hill and subject of the documentary film of the same name, squatted in a former artist’s shack on Greenwich Street for many years, studying and getting to know the birds. The book and film are highly recommended for anyone desiring a fascinating perspective on Telegraph Hill. And thanks to the imported-bird ban instituted in 1992, no more parrots are hatching escape routes from their cages. Today’s San Francisco parrots are free at last.

Alta dead-ends, so backtrack to Montgomery, turn left, and turn left again onto Union Street, which leads to a nub called Calhoun Terrace. Here some of the city’s oldest houses rub shoulders with modern masterpieces. The

Kahn House, at 66 Calhoun, is the work of Richard Neutra, the architect often credited with introducing the International style of modern architecture to California. His cliffhanger doesn’t look at all out of place here, and its expansive windows fully exploit the view of the bay. For the best vantage point, walk a little ways down the Union Street steps and look up at Neutra’s building. Loop around to the upper side of Calhoun. The house at 9 Calhoun was built in 1854—very early days for this city—and it has been lovingly restored.

Return to Montgomery Street, and head left to meander back down to North Beach. Half a block past Union, Montgomery dead-ends, and the steps leading down afford a perfect perspective of the Transamerica Pyramid and the Financial District skyline. Continue descending and make a right turn to climb our final set of stairs, the lushly planted Vallejo Street steps. Be sure to keep turning around for beautiful views of the bridge through the swaths of roses and bougainvillea that grace the staircase. It’s a straight shot to

Caffè Trieste in North Beach (see Walk 7), where an espresso or beer surely has your name on it.

Points of Interest

Mama’s on Washington Square 1701 Stockton St.; 415-362-6421, mamas-sf.com

Maybeck Building 1736 Stockton St. (no published phone number or website)

Coit Tower 1 Telegraph Hill Blvd.; 415-362-0808, tinyurl.com/coittower

Julius’ Castle 1541 Montgomery St. (no published phone number or website)

Grace Marchant Gardens Filbert St. and Napier Ln.; gracemarchantgarden.com (no published phone number)

Malloch Building 1360 Montgomery St. (no published phone number or website)

Kahn House 66 Calhoun Terrace (private residence)

Caffè Trieste 601 Vallejo St.; 415-392-6739, coffee.caffetrieste.com