I’m drawn to San Francisco’s many humorously similar street names, which are liable to confuse both locals and out-of-towners. Prominent examples are Mason St. and Masonic Ave., or Divisadero St. and Division St.

Which leads to the question: Why did city planners choose names so closely aligned? Especially since there’s so many names available?

The answer, of course, is “It’s complicated.” San Francisco may be a young city by historical measures, but it has a convoluted history. There are numerous sources for names, especially in terms of languages, cultures, politics, and notable people who made the city what it is today. Duplicate street names have haunted San Francisco for over a century.

On the flip side, while countless name pairs and triplets may have similar spellings, I’ve avoided including every remote similarity, out of the abiding sense that most are not humorously confusing. Has anyone ever mistaken Filbert St. for Fillmore St.?

And while a street might have an attached or nearby appendage with the same name (like a court, terrace, or alley), I don’t count them as “confusingly similar,” as that’s a normal naming practice (such as Ashbury St. and Ashbury Terrace, or Van Ness Ave. and South Van Ness Ave.)

Finally, I reserve the right to include streets just because. It’s my list.

Top tier

Divisadero St. / Division St.: Divisadero doesn’t mean “division” or “divider” in Spanish, but rather “a lookout point.” Early colonizing Spanish named nearby Lone Mountain El Divisadero. Division St. does seem to be a dividing line (between South of Market and the Mission District), but why that particular demarcation deserves a special name is beyond me.

Francis St. / Francisco St.: As Francisco is the Spanish name for Francis, not only do these street names sound similar, they’re identical once translated.

Folsom St. / Fulton St.: “Folsom” and “Fulton” are so damned close in pronunciation, whenever someone tells me one of the names, I have to take a moment and clarify in my head which they’re speaking about.

Geary St. / Geary Blvd.: These are actually a single stretch of road. The eastern portion of Geary St. extends from Market St. to Van Ness Ave., where it transforms into Geary Blvd. From there, Geary Blvd. runs to its terminus at 48th Ave. (near Lands End). Even people who live or work on Geary get this confused, and will refer to the eastern end as “Geary Boulevard” and vice-versa.

Lincoln Blvd. / Lincoln Ct. / Lincoln Way: Other than being named after the president, these three have no geographic connection. Lincoln Blvd. runs through the Presidio, Lincoln Ct. is in the Crocker-Amazon neighborhood, and Lincoln Way is the lengthy road running along the southern edge of Golden Gate Park in the Sunset District.

Mason St. / Mason St. / Mason Ct. / Masonic Ave.: Damn, this city likes naming things “mason.”

When you mention Mason St. to a San Franciscan, they’ll think of the road that runs through the Tenderloin, up and down Nob Hill, and into North Beach. Someone from out of town might confuse Mason with Masonic Ave., an arterial road in Midtown.

Maddeningly, there’s another Mason St. in the Presidio, on the northwest corner of the city (it runs alongside Crissy Field). On Treasure Island, you’ll find a Mason Ct. (See “Presidio Madness” and “The Treasure Island Effect,” below.)

Park Presidio Blvd. / Presidio St. / Presidio Blvd.: Park Presidio (the city’s original moniker for what is today called the Richmond District) connects Golden Gate Park with the Presidio. To its east, Presidio St. runs from Geary Blvd. to a southern gate of the Presidio, where it becomes Presidio Blvd. (See “Presidio Madness,” below.)

Also note that most of Presidio St. is wider than Presidio Blvd., in defiance of the usual understanding of the difference in those words.

State Dr. / States St.: This may be the biggest “WTF?” on this list. State Dr. is located near San Francisco State University, while States St. is up near Corona Heights. Which states are States St. honoring? I doubt anyone knows.

Union St. / Union Square: Sure, Union Square isn’t a street, but Union St. runs nowhere close to it. Yes, I’ve met multiple people who swore they were connected…until they discovered they weren’t.

Vandewater St. / Water St.: Both North Beach streets are more like alleys, and they run darn close to each other. Several theories have been floated (ahem) as to the identity of the original Vandewater (or Van de Water, or Van Dewater), but none have anything to do with water or the bay. Meanwhile, Water St. appears to be named after the original bay shoreline, which used to run nearby until landfill expanded North Beach and created what is today Fisherman’s Wharf.

Numbered avenues vs. numbered streets

These are easily the most confusing of the similarly-named streets in San Francisco, and the most common reasons tourists (and locals!) so often find themselves at an address in a neighborhood distant from their intended destination.

The numbered avenues run north-south from 2nd Ave. to 48th Ave. in the Richmond and Sunset Districts. Arguello Blvd. is the actual “1st Ave.”; don’t ask me why the number is skipped.

Unbelievably, there used to be a second set of numbered avenues in the Bayview District. These were suffixed with “South” to differentiate them from their twins on the west side of town. (So, “4th Avenue, South,” etc.) Their names were changed in 1909 as part of a massive (and controversial) street renaming project.

Meanwhile, the numbered streets run northwest-southeast, from 1st St. to 13th St. (due to Market St.’s strange orientation on the city grid), then level out and run east-west, from 14th St. to 30th St. They cover SoMa, the Mission District, the Outer Mission, and Noe Valley.

Thankfully, the numbered avenues never intersect with the numbered streets. However, due to the numbered streets curving their orientation halfway through their run, 8th St. improbably intersects 15th St. in Mission Bay. You can’t win in this town.

Of note

Beach St. / La Playa St.: Translated, La Playa is “The Beach,” meaning these are two more streets with essentially identical names.

Columbus Ave. / Columbia Square: No one will confuse Columbus Ave., the bustling thoroughfare running through North Beach, with Columbia Square, an easily overlooked one-block side road bordering a characterless park within spitting distance of Highway 80. Still, it’s amusing to wonder if an early beta of MapQuest once sent hapless frat boys desirous of strip clubs and Fernet shooters to this nondescript stickball lot.

Gold St. / Golden Ct.: Considering how important gold was to the founding of San Francisco, I’m surprised there aren’t more streets named after it.

Hearst Ave.: William Randolph Hearst, the namesake for Hearst Ave., played such an outsized role in local and national politics, yet is “honored” by a short sleepy street in the rather suburban-like Balboa Park neighborhood. (No, Hearst Ave. is nowhere close to the house Patty Hearst was arrested in, which is two miles away on Morse St. in Crocker-Amazon.)

Main St. & Central Ave.: I’ve long wondered who thought these two deserved their prized monikers.

In most American towns, Main St. is the “heart” of the city—there’s a reason Disneyland opens onto Main Street, U.S.A. Not so in San Francisco. Main St. is downtown, sure, but it’s a strangely dead thoroughfare, six lanes of road between rows of anonymous warehouses and office space. There’s no place to leave your heart along San Francisco’s Main St.

There’s a plot twist, though: Main St. is named after Charles Main, a harness maker and director of the San Francisco Central Railroad.

Speaking of Central Railroad, “Central Avenue” conveys big-city hustle and bustle, not this quiet neighborhood street on the edge of the Haight-Ashbury District. Later, I realized the name was more literal: Central Ave. runs near the geographic center of San Francisco.

Main St. / Main Dr.: This is a historic twinning, since Main Dr. no longer exists. It was the original name of JFK Dr., the squiggly east-west spine running through Golden Gate Park, from the Panhandle to the ocean. It’s now a pedestrian-only promenade, far more dynamic and beloved than Main St.

Mount Lane: May be the only street in San Francisco where all elements of its name can be abbreviated: Mt. Ln.

Nellie St. / Nelson Ave. / Nelson Rising Lane: I can personally attest that if you’re male with the last name “Nelson,” you will be called Nellie at several points in your life, hence my inclusion of Nellie St. in this group.

Don’t be mistaken and think Nelson Rising Lane somehow reflects a change in altitude due to San Francisco’s many hills. It honors local businessman and Fed chairman Nelson Rising.

Park St. / Park Blvd: Park St. straddles the line between Bernal Heights and St. Mary’s Park neighborhoods (although the park in question is the oval Holly Park). Meanwhile, Park Blvd. runs among the trails in the Presidio’s woods. (See “Presidio Madness,” below.)

The Hills of San Francisco

Hill St. / Hillway Ave. / Hillview Ct. / Hillcrest Rd. / Hillcrest Ct. / Hill Point Ave.: While local lore says there’s Seven Hills of San Francisco (c.f., the Seven Hills of Rome), the true number is somewhere in the forties. We do have six streets with “hill” in them, though. If city planners could find one measly stretch of asphalt and give it a “hill” name, boom—there’s your Seven Hills of San Francisco.

(My nomination? The so-called John’s Way, an officially unnamed stretch of road near Twin Peaks. John’s Hill?)

Presidio Madness

San Francisco’s Presidio throws a monkey wrench into the street naming game.

Founded in 1776 by the Spanish, the Presidio has been a military base for almost its entire history, and therefore not subject to city planning. Many of its streets have similar—or identical—names in San Francisco proper, with no geographic connection between the two.

My favorite? Montgomery St. & Montgomery St.

In San Francisco, Montgomery St. is a major thoroughfare in the Financial District, bounded on both sides by skyscrapers, banks, investment houses, and consulates. When you see a luxury car commercial filmed on slick roads lined with august institutions and white-marble colonnades, that’s probably Montgomery St. in the Financial District.

The other Montgomery St.? Just another of the Presidio’s charming lanes running between colonial-style red-brick halls and fields of grass. It’s miles from the Financial District.

Nearby roads in the Presidio include Anza, Taylor, and Arguello—all with twins in San Francisco. To round out the field, a second Mason St. runs along Crissy Field.

The Treasure Island Effect

As with the Presidio, Treasure Island was a military base until the 1990s. It too has its own set of street names twinned with streets in its host city, including California, Howard, and Kearny. The ever-popular Mason name makes another appearance, in the form of Mason Ct.

To add to the fun, Treasure Island also has its own numbered streets, just like the numbered streets in the Mission District. Yes, Virginia, San Francisco has two 4th Streets—but, thankfully, only one Virginia Ave.