Start at the southwest corner of Union and Montgomery in front of Cadre, the framing shop at 301 Union (#1) (the location of the former Speedy’s market) to begin your self-guided walking tour of the Telegraph Hill Historic District. By the time you finish, you will have traversed some ten blocks and seen just about all of the Historic District’s approximately 100 buildings.
Although this building is just outside the Historic District, Speedy's market was a fixture on the Hill, serving its residents for almost 93 years until closing in 2008. The Spediacci family from which it took its name bought the building while it was under construction in 1915 and operated the market for over 35 years.
Directly across the street, at 1301 Montgomery (#2), you will see what at first appears to be a nondescript building. But hidden under its tan-colored painted plaster is the only brick building in the District. Dating to c. 1852, it is one of the two oldest buildings in the District and possibly the oldest extant brick building in San Francisco.
Now turn right, staying on Union as you cross Montgomery towards the Bay. If you look to your right as you cross, you’ll see the Transamerica Pyramid serving as a vivid backdrop to the Hill’s crest, an off-used setting for filming ads and movies, as well as wedding and fashion shots. This crest marks the District’s highest spot, 218 feet above sea level, second in height only to Coit Tower itself, which lies outside the District boundaries.
Walking down the one remaining block of Union, take a right on upper Calhoun Terrace. The Work Progress Administration (WPA) built the high retaining wall that separates upper and lower Calhoun in 1939-40. The only old structure remaining on either terrace is 9 Calhoun (#3). Built in 1854, this balconied Gothic Revival building is the third oldest dwelling in the District and was the home of Dr. David G. “Yankee” Robinson, a physician, actor and manufacturer of bitters. Because it had its own spring, the owners did not request to be connected to the City’s water system until 1872.
With you back to 9 Calhoun, and with a stunning downtown view on your right, look down upon lower Calhoun Terrace where you will see two examples of the Modern architecture that came into the District in the late 1930s – buildings significant for their architects who achieved fame. The most celebrated is the Kahn House at 66 Calhoun (#4). Built in 1939, it was designed by Richard Neutra one of the founders of the International Style.
Next-door is Ian Hoeffler’s apartment building at 38–50 Calhoun (#5) (telltale “portholes” in the front façade) built in 1937 in the Moderne Style. The apartment at 42 Calhoun was a temporary residence of Frida Kahlo and Diego Rivera in 1940. You may have to move a bit to the right to see the “cascading” of the apartments down the slope towards Sansome.
Making your way back towards Union Street, you may wish to turn right, downhill past the wall at the street’s bottom, to enjoy the view from a lovely, privately maintained garden, a feature found elsewhere in the District, as we shall see.
As you retrace your steps back up Union Street, see on your left the three-story, wood-frame, balconied dwelling at 291 Union (#6), which competes with the brick building at 1301 Montgomery as to oldest structure in the District. Constructed by John Cooney in 1853 on a lot acquired by deed dated in 1850, it was the first and for a while the only store on top of the Hill. According to David Myrick in San Francisco’s Telegraph Hill, the wood for its construction accompanied the Cooneys from Australia and they lived in a tent on the lot during construction to prevent its theft. Cooney’s descendants lived there until 1937.
In 1857, the Cooney family also built the (now purple) “Gothic Revival” cottages next door at 287-289 Union (#7) as rental units.
On the southeast corner of Union and Montgomery is 1254-1256 Montgomery (#8), constructed 1861 (corner and upper story c. 1887) on the site believed to be the former location of Hudson's Windmill. Listed on the National Register of Historic Places for its architectural and historic significant, the building was originally a rooming house with twenty-five rooms, all with a door to a hall, and most with additional doors to any adjoining room in case a family wished to rent more than one room. At some uncertain time, the building was converted to six railroad flats.
Now head downhill on Montgomery and turn right onto lower Alta. Almost immediately you will spot the two balconies of 31 Alta (#9) essentially unchanged since Captain Andres built it in 1858. The Telegraph Hill Tavern flourished briefly in its basement, and in its backyard the Peach Blossom Festival was held by Silvio Catelli in the 1950s.
A few doors down, is 21 Alta (#10), built in about 1862. This Italianate structure, once occupied by Michalsen Grocery, has been restored and you can now see its original store entryway, which was revealed during the restoration and retained.
At the end of Alta, take a look over the retaining wall for a view of the Grace Marchant Garden, the Filbert Steps and Napier Lane where we’re heading next.
Heading back up the street you will see the “Duck House” at 60 Alta (#11). Architect William Wurster, founder of the Second Bay Area Tradition Style, built this home for muralist Helen Forbes in 1935. Go past it and see the ducks after which this dwelling takes its name, frescoes according to a traditional Italian formula by Helen Forbes and Dorothy Puccinelli, who also painted the murals that adorn the Mothers Building at the SF Zoo. It was here in the 1970s, that Armisted Maupin began writing Tales of the City as he watched the goings on below him on Napier Lane.
At Alta and Montgomery, turn right and head downhill the short block to Filbert. Just at the corner, look up at 1360 Montgomery (#12), known as the “Malloch Building.” Etched into the glass over the central entrance are a gazelle, palm trees, and ocean waves. Sgraffito wall decorations, created by carving into several layers of cement, adorn both the Montgomery and Filbert sides and include a worker holding the world above the Bay Bridge. Architect Irvine Goldstine designed this 1936 building with contractors-owners Jack and Ralph Malloch. The etching and wall decorations are by Alfred Dupont. It is one of the most photographed buildings in the District, famous as the setting for the 1947 movie, Dark Passage, staring Humphrey Bogart Lauren Bacall.
Now turn right, down the Filbert Steps into the heart of the Historic District. Pause a moment to read the plaque dedicated to Grace Marchant, whose selfless and gargantuan efforts created the gardens you are about to enjoy.
Down the steps past the plaque, your path zigs left in from of a pump station essential to the fire safety of this portion of the District. If you wish, you may venture straight ahead along Darrell Place, a one-block pedestrian path that will require you to turn around and return to the steps. Imagine it a century ago when, called Norton Place, it contained but two houses separated by a saloon. At 20 Darrell Place (#13), take a peek at the studio apartment in the basement, once inhabited by Barbary Conrad, the writer, painter and bullfight aficionado, who founded El Matador on Broadway in the early 1950s.
Continuing downhill on the Filbert Steps, you’ll find a series of small cottages and homes on your left that comprise one of only two complete stretches of pre-1870 buildings remaining in the District.
The first is the tiny clapboard cottage at 230 Filbert (#14). Built in 1858 by William F. Ross, laborer and longshoreman, it is essentially unchanged.
A top contender for the most outstanding contributor to the District is the Gothic Revival house at 228 Filbert (#15) built in 1869 by Phillip Brown, a seaman turned stevedore. It is sometimes referred to as the “Captain’s House” because Captain Laughton was a frequent visitor who spent so much time on the front porch that people incorrectly assumed it was his home.
Next are the Farley House at 226 Filbert (#16) and Gothic Revival home at 224 Filbert (#17) (at the northwest corner of Filbert and Napier Lane). Both date to 1859 and were built by laborers on the Waterfront.
Napier Lane joins the Filbert Steps at the heart of the Grace Marchant Garden, whose beauty and exotic floral proliferation deserve a stop to read the plaque to Gary Kray, Grace’s neighbor, friend and protégé, who carried on her work for 33 years until his death in 2012. Before he died, Gary passed the torch as official gardeners to Paula McCabe and Larry Habegger who are now carrying on Gary’s (and Grace’s) legacy, continuing the long tradition of voluntary service they established.
Now walk down Napier Lane (formally Billings Place), the only boardwalk surviving in the District and one of the few left in San Francisco. Almost immediately on your right at 8 Napier (also 222 Filbert) (#18) in the brown-shingled building (shingles added in 1968), which was the home of Grace Marchant while she created and tended the Gardens during the 1950s. This 1879 building was originally the home and grocery store of Michael Thornton, who operated his shop on the bottom level for about 40 years until he passed away in 1918. In the early days, there may have been a saloon here – some say Thornton operated a “blind pig” (selling booze without a license).
Next door at 10 Napier (#19) is the oldest structure on the lane, vying for fourth oldest in the District and essentially unchanged. Its Italianate false front likely dates from about 1887, but if you stand just between Nos. 8 and 10, and look 6-8 feet inwards, you’ll be able to detect the outline and roof of the original board-frame cottage, dated to 1857. Its original owners were Murty and John Clark, teamster and warehouse laborer, respectively.
Just a few steps further down the lane, on the other side, take a look at 21 Napier (#20). Built by at least 1880, it’s a good example of multi-story balustrade balconies and stairs on the front.
Several of the other dwellings on the lane have been remodeled, but largely preserved and restored, thanks in part to the historic district legislation. Take a look at 32-34 Napier (#21) at the very end of the lane. Originally built in c1895, this house was reputedly used for shanghaiing sailors in the early days.
Returning to the Filbert Steps, turn left downhill past passing from the wooden steps and the gardens onto the vertiginous concrete stairs, were we’ll leave the District briefly to make our way around the block to the Greenwich Steps – turning left on Sansome and left again on Greenwich where you’ll confront another set of concrete stairs, which, once mounted, will have you back in the District.
At the top of the stairs, pause to peek over the gate to 221 Greenwich (#22), whose asymmetrical gable roof you can barely make out. Tucked back between Greenwich and Napier, it’s dated to 1857, as is 237 Greenwich (#23) (in the Heslett compound), two of the oldest buildings on the Greenwich Steps you are about to traverse.
As you proceed along Greenwich, you may be reminded of the Grace Marchant Gardens, as well you might. It was here that Grace first settled upon moving to San Francisco (at 235 Greenwich) (#24), and where she and her daughter, Valetta Heslett, created the gardens along the Greenwich Steps. Valetta and her husband, Desmond, ended up buying and rebuilding the haphazard cluster of small buildings you see on the south side of the stairs which became known as the Heslett compound. For a look at the colorful history of the compound, go to Mark Bittner’s website: http://www.markbittner.net/writings/heslet.html
Just as you leave the upwardly sloping sidewalk and begin your ascent up more flights of steps, note the gray cottage to your left at 285 Greenwich (#25) (its mailbox is around the corner at Montgomery), originally built in 1886, but moved to its present location to make way for the construction in 1936 of the Moderne style building at 1470 Montgomery (#26), the last building in the historic district. All of the other buildings in the 1400 block of Montgomery are excluded from the District.
As you reach the top of the Greenwich Steps at Montgomery, take a look at Julius’ Castle at 302 Greenwich (#27) constructed in 1923 and expanded in 1928 by Architect L. Mastropasqua. Until 2008, Julius’ Castle was one of San Francisco’s oldest continuously operated restaurants in its original location. Although not part of the Historic District, it is designated as City Landmark No. 121.
From Julius Castle, walk slightly uphill on upper Montgomery towards Union Street. As you cross upper Alta, you once again enter the District. A very nice last stretch is this, as the next three dwellings, some altered, have been dated to the 1860s and the forth (at the corner) is 1301 Montgomery (#2), the District’s oldest, bringing us back to where we started. Right in between them is School alley, the District’s narrowest street at 8 feet, 5 inches, certainly worth a stroll down its short, brick-covered length, as a fitting end to this District walking tour.
Below is a list of the surviving buildings within the Telegraph Hill Historic District by date, including their first known occupants or owners and architectural style.
1301 Montgomery - first know likely a salesroom and “bitters manufactory” for Dr. David G. “Yankee” Robinson (commercial brick building)
291 Union - John Cooney, grocer (Italianate)
9 Calhoun – Dr. David G. “Yankee” Robinson, physician, comedian, theatrical entrepreneur and bitters manufacturer (Gothic Revival)
221 Greenwich – George Mitchell, longshoreman (Vernacular cottage)
237 Greenwich – John McDonough, longshoreman (Italianate)
10 Napier Lane – Mortimer “Murty” and John Clark, teamster & laborer at Greenwich Dock Warehouse (Italianate)
287-89 Union – Cooney Rental Units, John Cooney, grocer (Gothic Revival)
31 Alta – Richard Andrews, stevedore (Greek Revival)
230 Filbert - William F. Ross, laborer, later longshoreman (Vernacular cottage)
224 Filbert – James Callaghan, laborer; later foreman at North Point Warehouse (Gothic Revival)
226 Filbert – Farley House; James Farley, laborer (Greek Revival)
1304A Montgomery – Duncan Campbell, rigger and stevedore (Vernacular cottage behind 1304 Montgomery)
218-20 Filbert (upper stories added in 1882) – Patrick McDermott, laborer (Italianate)
1254-56 Montgomery (corner and upper story c.1887) – George Smith, grocer (Italianate); Listed on the National Register of Historic Places
1305-07 Montgomery – William B. Smith, stevedore (Italianate)
21 Alta – Richard Andrews, stevedore, site of Michalsen Grocery (Italianate)
33 Alta (left portion) - James Harrington, warehouseman, later watchman (Greek Revival)
216 Filbert (remodeled in 1959) – Andrew Benson, later James Gorman, stevedores
1308 Montgomery (altered, bay added) – Joseph King, stevedore (Italianate)
1309-11 Montgomery – Patrick Heffernan, laborer; Italianate style
1313-15 Montgomery – Michael Carr, fireman on steamboat; Italianate style
 Information from Telegraph Hill Historic District Case Report prepared by Anne Bloomfield and adopted by the Board of Supervisors as part of District designation in 1986.