The City of West Hollywood was officially incorporated as its own municipality in 1984 — but its history starts way before that.
Originally a rough-and-tumble settlement for railroad workers in the late 19th century, the town of Sherman — named after its co-founder, Moses H. Sherman — arose out of those train tracks (which carried everything from streetcars to freight trains) to become a Hollywood-adjacent community that attracted both residents and commercial entrepreneurs.
But, unlike Hollywood, it was never annexed by Los Angeles. And it’s remained fiercely independent.
You can get to know West Hollywood by exploring its earliest and most enduring “Main Street,” a.k.a. Santa Monica Boulevard, which runs the entire length of the modern-day city, from west to east.
Its western end is known by the nicknames Boystown and the Rainbow District, both in reference to the heart of WeHo’s LGBTQ community. It’s also where the West Hollywood Halloween Carnaval and the LA Pride Parade & Festival take place.
But what locals and visitors may not immediately see are the layers of time — nearly 100 years’ worth — that make West Hollywood the fascinating L.A. metro city it is today.
And not only is it walkable — but it’s also bikeable, with protected bike lanes on both sides of Santa Monica Boulevard. Just be sure to follow local rules for bicyclists (including no riding on sidewalks where there’s a bike lane).
If you don’t have a bike of your own, you can rent (or buy) one locally from Bike Shop LA (which is affiliated with Bikes and Hikes LA). Before you set off, make sure you check out the West Hollywood Bicycle Coalition’s tips for riding safely.
So whether you’ve got your own wheels or need to borrow some, here are some of the most fascinating points of interest along the first mile of West Hollywood — from intriguing public art to a cornucopia of architectural styles, and even some rock and roll history.
1. The Fruechtl Building, 9091 Santa Monica Boulevard
Start your journey at the western gateway of West Hollywood, at the intersection of Doheny Drive and Santa Monica Boulevard. On the northeast corner, you’ll find a triangular-shaped brick building that was constructed for mixed use in 1924 — apartments upstairs and retail downstairs. That was when the area was still known as “Sherman.” It wouldn’t become West Hollywood until the following year.
Designed by California architect Frank Frederick Rasche for Melba Drugs proprietor Leo M. Fruechtl, the building marks the boundary between West Hollywood and its neighbor to the west, Beverly Hills — especially with a billboard prominently placed on its rooftop from the time of the building’s completion until today. Although the Fruechtl building housed thriving businesses even after Melba Drugs (like Rexall Liquor Store in the 1940s and Abigail’s Flowers/Aardvark Balloons in the 1980s), its commercial spaces have been vacant for nearly 30 years.
Its conspicuous corner location is indicative of the type of commercial development that sprung up around streetcar lines — including the Pacific Electric line that used to run right down the middle of this stretch of Santa Monica Boulevard, all the way out to Santa Monica. The tracks are now long gone, replaced with a landscaped median that features rotating public art installations. But look up, and you may be able to spot a ghost sign that reads “Melba Drugs” and “BROMO SELTZER” on the east-facing side of the Fruechtl building.
2. The Troubadour, 9081 Santa Monica Boulevard
Built in 1946, the two-story building that’s housed the Troubadour live music venue since 1957 is probably best known as a legendary hotspot for early-career performances by the likes of such folk-rock titans as Bob Dylan, The Byrds, Buffalo Springfield, James Taylor, Joni Mitchell, Gordon Lightfoot and Neil Young. Elton John made his U.S. live debut there. It’s where future bandmates Don Henley and Glenn Frey met, later to form The Eagles. It’s also said to be where Janis Joplin partied the night away before fatally overdosing on heroin.
Troubadour founder Doug Weston has been called “the godfather of the Southern California singer-songwriter movement,” discovering new acts and booking headliners in his 300-seat venue who would go on to sell out stadiums around the world. His name now adorns the building façade and its attached sign.
There are almost too many Troubadour stories to tell — from Lenny Bruce getting arrested on obscenity charges in 1957 to Richard Pryor performing as the opening act for Nina Simone in 1965. Numerous live albums have been recorded on the iconic nightclub’s stage; several comedians have been discovered there, from Cheech and Chong to Steve Martin. And until COVID-19 restrictions shut down live music venues, it was still hosting hot ticket concerts by both heritage artists and up-and-comers. Pay your respects when you pass by now, but make it a point to grab a drink in the tavern and catch some live music when it’s safe to do so again.
3. Dan Tana’s, 9071 Santa Monica Boulevard
Originally built as a Colonial Revival-style single-family home in 1929, the bright yellow cottage with white shutters on the north side of Santa Monica Boulevard has been home to Dan Tana’s Restaurant since 1964 (then called only “Tana’s”) — and it retains many of its original architectural details (despite a disastrous fire in 1980). Its founder, Dan Tana, was a Yugoslavian-born soccer pro who washed dishes at Miceli’s in Hollywood and worked his way up to maître d' at La Scala in Beverly Hills before striking out on his own. His namesake restaurant is still renowned for its tuxedoed waiters, Croatian bartenders and hearty portions of Italian comfort dishes like chicken parm.
Tana’s predecessor in that spot was Dominick’s, another Italian eatery formerly known as Domenico’s Lucky Horseshoe Café (or just Domenico’s Lucky Café). Before that, it was a counter lunch joint called Black’s Lucky Spot Café. If you look closely at the green neon sign that adorns the front of the building, you can see the “ghost” of the old horseshoe sign — the same sign that trolley passengers would see as they passed by on the Pacific Electric Red Car.
Dan Tana’s celebrity clientele has included actors like Dabney Coleman and Harry Dean Stanton, as well as musicians Don Henley and Glenn Frey of The Eagles (who infamously wrote their hit song “Lyin’ Eyes” while sitting in one of the red leather booths). To experience it for yourself, call ahead to pick up lunch or dinner to go, seven days a week, starting at noon daily. Outdoor dining is offered in the evenings, when local health restrictions allow for it.
4. Heritage Classics Motorcar Company, 8980 Santa Monica Boulevard
The Heritage Classics Motorcar Company was founded as a classic car dealer in the 1980s and moved to its 10,000-square-foot location in West Hollywood in 1992 — becoming the largest classic car showroom in Los Angeles, a distinction it still holds today. The stuccoed, Spanish Colonial Revival style structure was built in 1931 for the Howard Preston Co. Ford Dealership, which shuttered its operations in the midst of the Great Depression.
Starting in 1933, a number of non-automotive enterprises occupied the space, from heating companies to a furniture warehouse. But in 1966, with the arrival of the Auto Europa dealership, it returned to its original purpose — and it remains the most intact car dealership of its kind in West Hollywood. It currently sits directly adjacent to the proposed Robertson Lane mixed-used development and is for lease, though Heritage Classics still occupies the space.
5. 'Rockin’ Angel' and 'Murano' sculptures, approx. 8800 Santa Monica Boulevard
In 2009, Echo Park-based sculptor Peter Shire contributed two geometric pieces to the Santa Monica Boulevard median, as part of West Hollywood’s Urban Art Program of permanent public words: “Rockin’ Angel” and “Murano.” Located approximately across from L.A. Buns and the Santa Palm Car Wash, they’re visible from either the eastbound or westbound side of Santa Monica Boulevard’s bike lanes.
6. Fife Building, 8701 Santa Monica Boulevard
One of the fanciest buildings you’ll see along this stretch of WeHo is the work of the Morgan, Walls & Clements architectural team at the Fife Building, completed in 1929. Designed in the Spanish Gothic Revival architectural style, it features decorative ironwork, an ornate roofline with a corner tower and intricate masonry — all befitting a building that once marked the eastern boundary of the Sherman (a.k.a. West Hollywood) commercial district at the time it was built. It’s now home to a beauty salon, a bakery and more.
7. 'Surfboard Tiki' sculpture, 8585 Santa Monica Boulevard
Another Peter Shire sculpture adorns the front of the Ramada WeHo hotel on the north side of Santa Monica Boulevard — “Surfboard Tiki,” which Shire created in 1987 and restored (with funds contributed by Ramada) in 2010. Also part of West Hollywood’s Urban Art Program, this piece can be found by the entry driveway of the hotel, situated just off the sidewalk between Wells Fargo Bank and Kitchen 24 (and while you’re there, why not snag a takeout skillet cookie to bring home with you?).
8. 'West Hollywood Clock' sculpture, 8520 Santa Monica Boulevard
On the south side of Santa Monica Boulevard, at the northeast corner of the Shake Shack parking lot, you’ll find another Urban Art Program permanent sculpture — this one by Nancy Mooslin, called “West Hollywood Clock,” from 1996. The painted steel piece rises 18 feet off the ground and simultaneously represents the 12 hours on a clock, 12 pitches in a musical octave, and 12 hues of a color wheel — all embodied in 12 different geometric shapes. Currently based in Santa Ana, Mooslin has contributed public works to other SoCal cities like Ventura, Escondido, Laguna Beach, Anaheim and more.
9. The Doors Workshop, 8512 Santa Monica Boulevard
At the front of Bar Sopra, just one door east of Shake Shack, look for a modest brass plaque that indicates the location of “The Doors Workshop” — that is, the building that The Doors used as an office, rehearsal space and a makeshift studio to mix and record Jim Morrison’s final album with the band L.A. Woman before his death in 1971. According to his Doors bandmates Ray Manzarek and Robby Krieger, Morrison laid his vocals down in the lower-level bathroom.
10. Alta Cienega Motel, 1005 La Cienega Boulevard
Another Jim Morrison “haunt” was Room 32 at the Alta Cienega Motel on the northwest corner of Santa Monica and La Cienega Boulevards, where he lived from 1968 until his 1971 death in Paris. You can actually specifically request to book the “Jim Morrison Room” by the hour or by the night — although you’ll have some competition, as fans flock from all over the world to scrawl messages on the room’s walls in tribute to the fallen “Lizard King.” To learn more about Morrison’s time in West Hollywood, join one of Jon D'Amico's Rock 'n Walk Tours.
11. CVS Pharmacy, 8491 Santa Monica Boulevard
You might not normally notice a CVS Pharmacy — but this one, located on the northeast corner of Santa Monica and La Cienega Boulevards, is ginormous. There’s a good reason for that, too: It was built as a bowling alley, which opened in 1940 as La Cienega Lanes (and, later known as Art Linkletter’s La Cienega Lanes). It boasted air conditioning, automatic pinsetters and an onsite restaurant. And that’s just the beginning of this building’s fascinating history.
In the 1970s, as the popularity of bowling began to wane, the huge corner building transformed to offer the latest trend: roller disco. Flipper's Roller Rink (or, as the sign read, FLIPPER’S ROLLER BOOGIE PALACE) — named after its co-founder, British music producer Ian “Flipper” Ross — opened in 1979. With the fall of disco, however, it couldn’t survive past the year 1981 — despite having become a celebrity magnet (including one-time co-owner Cher). Even transforming into a punk/new wave club couldn’t save it.
So, the building itself got converted into a 19,000-square-foot retail space — first by Esprit (until 1994) and then a series of drug stores, with CVS taking over in 2006 and remaining to this day. The concrete parking structure was added in the 1980s, and the interior has been completely redone with no remnants left of its glittery history. But the corner façade has amazingly retained its curved look and is immediately recognizable when compared to historic photos.
Bonus: The Holloway Motel, 8465 Santa Monica Boulevard
Just east of CVS on the north side of Santa Monica Boulevard is the only remaining motel along the West Hollywood stretch of Route 66: the Holloway Motel. Although it closed at the beginning of the COVID-19 pandemic, it’s worth a detour to take a gander at its Colonial Revival-style architecture, which dates back to the motel’s completion in 1954. The West Hollywood Preservation Alliance has campaigned for the motel to be included in the city’s Commercial Historic Resources Survey, although it’s been officially deemed ineligible for inclusion.