Walk the block around Fair Oaks and Colorado this month and you'll notice something new pinned to the lamp posts and taped in a few shop windows: centennial banners, a Route 66 shield here and there, flyers for a car show. If you live in Old Pasadena, you've probably already wondered what the fuss is about. The short answer is that Route 66 turns 100 on November 11, 2026, and Colorado Boulevard, the street the highway runs down through this neighborhood, turns 150 the same year.
Two anniversaries landing in the same twelve months looks like a nice bit of civic coincidence, and most of the coverage you'll find treats it that way. But the order of those two numbers tells you something the coincidence framing misses. Colorado Boulevard was Pasadena's working Main Street fifty years before there was a Route 66 to put it on. The highway didn't build this neighborhood's spine. It found one already standing and used it.
The Corner That Beat the Highway by Forty Years
Colorado Boulevard started as Colorado Street, and its history at the Fair Oaks Avenue crossroads goes back to 1876. By 1883, that same crossroads, the corner One Colorado now anchors a short walk from, already had a drugstore, a blacksmith shop, a cigar and news stand, a shoemaker, a couple of hardware stores, a harness shop, and a restaurant doing business. That's a functioning commercial block four decades before automobiles made Route 66 necessary, and more than forty years before the federal government drew the highway on a map in 1926.
That timeline matters because it flips the usual Route 66 story. Across most of the highway's original 2,400 miles from Chicago to Santa Monica, the road came first and the towns grew up alongside it, motor courts and diners built to catch drivers who had nowhere else to be. Old Pasadena wasn't one of those towns. When Route 66 needed a way through the western San Gabriel Valley, it borrowed a Main Street that had already been open for business since the Grant administration. The neighborhood didn't wait around for the highway to arrive. It kept the boulevard's own name, Colorado Street, right up until 1958, more than three decades after the highway was already running through it.
A Highway That Couldn't Sit Still
Here's the part most Route 66 nostalgia skips: nobody can hand you one clean line and say "this is exactly where the highway ran through Pasadena." Julia Long, who leads walking tours through the city, put it plainly to National Geographic: "It had many different route changes through Pasadena alone." That's not a footnote. It's evidence that the highway had to keep adjusting to a city that was already dense, already built out, and already inconvenient to reroute around.
The rough sequence looked something like this:
- The original 1926 alignment continued south on Fair Oaks Avenue toward what would eventually connect to Los Angeles.
- An alternate path crossed the Colorado Street Bridge, the 150-foot Beaux Arts span built in 1913, which carried Route 66 traffic through 1940.
- In 1940, the route shifted onto the newly opened Arroyo Seco Parkway, the first freeway built in the American West, replacing the bridge crossing as the preferred way west toward Los Angeles.
Small desert towns along Route 66 tend to have one alignment and one story about it. Old Pasadena has at least three, because the city kept changing under the highway's feet. The split itself happens right at Fair Oaks and Colorado, the same intersection that was already a commercial corner more than forty years before drivers needed directions through it.
What's Actually Happening Before the Banners Come Down
The double anniversary isn't an abstraction this fall. There are fixed dates on the calendar, most of them within walking distance of the historic district:
- On September 20, 2026, the Southern California Falcon Club is holding a Route 66 Centennial Classic Car Show at the restored Elks Lodge on Colorado Boulevard.
- The Pasadena Museum of History has a room dedicated to the Mother Road, with photos of local businesses, historic street signs, and an interactive route map on the wall, on view through the end of 2026 alongside the citywide recognition of both anniversaries.
- Melting Pot Food Tours runs its Old Pasadena walking tour, a 1.25 mile, roughly ten stop route starting at 155 S. Raymond Avenue, with this year's version built around Colorado Boulevard's Route 66 history ahead of the November 11 milestone.
- A few blocks east in Playhouse Village, the centennial calendar includes a Zoom conversation with authors Jim Ross and Shellee Graham about their book on the highway's first hundred years, alongside reminders that Vroman's Bookstore, founded in 1894, and The Ice House Comedy Club, the nation's oldest operating comedy club, were both already neighborhood fixtures long before the highway arrived.
None of this requires a road trip. Most of it is inside the neighborhood you already walk to get coffee.
Where the Boutique Blocks End and the Working Boulevard Begins
If you do want the fuller Route 66 experience, motels included, you'll need to drive east past the historic district's polished laneways. The Saga Motor Hotel, built in 1957 by architect Harold Zook specifically to catch the eye of passing drivers, still operates further up Colorado Boulevard, as does the 1962 Astro Motel, a surviving example of the Googie style. Last year, a new mural celebrating Route 66 went up at Villain Custom Cycles on East Colorado, painted by artist Victor Ving with support from a National Register of Historic Places preservation grant, timed deliberately ahead of this year's centennial.
That contrast is worth sitting with. Old Pasadena's stretch of Colorado Boulevard is the buttoned-up version of Route 66, restored storefronts, an open-air shopping center anchoring the historic corner, laneways that photograph well. A couple of miles east, the same boulevard is still doing the job it did for cross-country drivers in the 1950s: motels with vacancy signs, a motorcycle shop with a new mural, a highway that never stopped being a highway. Both stretches are technically Route 66. Only one of them was a Main Street first.
What the Two Numbers Actually Tell You
The centennial banners will come down sometime after November 11. What won't change is the order those two anniversaries happened in. Route 66 gave Old Pasadena a nickname and a mythology worth marketing. Colorado Boulevard gave the highway a street that already worked, complete with a blacksmith and a shoemaker, decades before anyone needed a road sign to find it. That's the version of the story worth knowing before the next centennial banner replaces this one, which will be a while.
If this corner of the neighborhood's history has you paying closer attention to what's actually built along it today, that same attention to Old Pasadena's specifics is what Shahe Seuylemezian at RE/MAX Dream Properties brings to every conversation about living here, including a look at Uptown Luxury Condos a few blocks over in the Playhouse District. Schedule a private tour to see what the newest chapter of this boulevard's story looks like from the inside.
