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Around 7 a.m. Saturday, in a lot beside the shuttered Santa Monica Civic Auditorium, a strange set of cars and trucks began to gather. Three Model A’s. A couple of ’60 convertibles. A 1964 Chevrolet Impala station wagon. Also, a big bull on trailer wheels.

“Am I in the right place?” asked a man in one of the Model A’s.

“Going to Chicago?” asked a guy in a white Denali.

“I wish I could do the whole thing,” said Joe Hernandez of Pasadena, wistfully standing by.

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This was the starting line for roughly 70 drivers who gathered to celebrate the centennial of Route 66 with a 2,448-mile, 20-day caravan to Chicago. Most had come from outside California to share an adventure with fellow “roadies” and boost awareness of the classic scenery and independent businesses along the eight-state route.

But soaring gas prices and hesitant international travelers have added uncertainty to a trip that was always going to be a logistical challenge. Day 1 alone might terrify an L.A. commuter: From the Pacific to Pasadena by surface streets, including miles on Santa Monica and Colorado boulevards.

“I don’t know how it’s all going to happen,” said Gary Daggett, president of the Old Route 66 Assn. of Texas. But he and his wife, Stephanie, have more than a little Route 66 experience to draw upon.

Mike and Lisa Visket of Prescott, Ariz., pose in Santa Monica at the pier in their Route 66 clothing on June 6, 2026.

“This is our 30th trip over 20 years,” Daggett said. “You can’t see everything. There’s so much…. You start meeting the people, you get hooked on the people.”

Shortly before their 8:30 departure time, organizer Rhys Martin called drivers together.

“Leaving here is going to be a little complicated,” he said.

Martin, who is part of the Route 66 Road Ahead Partnership, is president of the Oklahoma Route 66 Assn., and serves as manager of the National Trust for Historic Preservation’s Preserve Route 66 initiative. For the journey, he is driving a ’64 Chevy Impala station wagon with a GPS unit inside so that armchair travelers can follow his journey on the web.

“It’s going to be impossible to keep everybody together,” he said during preparations. “We’re encouraging people to spread out and support independent businesses rather than all going to one place and demolishing the kitchen.”

William Cooke of Pinon Hills participates in a caravan from Santa Monica Pier to Chicago, celebrating the centennial of Route 66.

In song and literature, the route is celebrated as an east-to-west journey. This caravan, running in the opposite direction, will travel from California through Arizona, New Mexico, Texas, Oklahoma, Kansas and Missouri to Illinois.

From Santa Monica, the Day 1 schedule took drivers to Beverly Hills City Hall, Grand Central Market downtown for lunch, the Chicken Boy statue and Galco’s Soda Pop Stop in Highland Park, then an overnight in Pasadena.

Day 2 takes the group from Pasadena to Barstow. Day 3, from Barstow to Needles. On June 25, the caravan is due to arrive in downtown Chicago.

The loose procession was led by a core group of 15 cars, including representatives of all eight states on the route. Since anyone can join or leave the caravan at any time, the number of vehicles will vary by the hour.

Through the decades, the road has grown from an American artifact into a global symbol of small-town Americana. Many merchants, restaurateurs and hoteliers along 66 now say that their summer customers are mostly travelers from abroad, especially Europe. One of the caravan’s drivers, in a rented pickup truck, was Dries Bessels, co-founder of the Dutch Route 66 Assn.

Brady Wilson of Amarillo, Texas, displays an assortment of Route 66 pins on his cowboy hat. Wilson is part of a caravan of Route 66 enthusiasts who set out from Santa Monica Pier on June 6, 2026, for Chicago.

Though the Model A’s will surely raise eyebrows on the road, the caravan’s most startling element is the fiberglass bull representing the Amarillo-based Big Texan Steak Ranch restaurant, one of the event’s sponsors.

“It’s the same one my dad brought home in ’71. His name is Big Moo,” said Danny Lee, who co-owns the restaurant with his brother, Bobby Lee. “He’s 12 and a half feet high. About 500 pounds. It’s all fiberglass.”

In 21 cities along the drive, the Big Texan team aims to stage nightly steak-eating contests, giving free dinners to anyone who can eat 72 ounces of steak, a baked potato, three shrimp, a side salad and a roll in 60 minutes.

The caravan’s first challenge came at the Santa Monica Pier, where there was no room for the cars due to a construction project, World Cup preparations and a Children’s Hospital fundraiser. Instead, the caravan gathered by the Santa Monica Civic Auditorium. Drivers strolled over the pier for a photo op, then returned to their cars.

“Herding cats,” said George Kulakowski of Huntington Beach, at the wheel of a 1931 Ford Model A Panel Delivery truck.

Participants in a Route 66 centennial caravan pose for a photo before they depart from Santa Monica Pier on June 2, 2026, for Chicago along the historic highway.

Another challenge awaited in West Hollywood, where Santa Monica Boulevard (aka Route 66) was busy with crowds for the city’s WeHo Pride Street Fair. By plans laid ahead of time, most caravan vehicles detoured around the party while select caravan cars followed a police escort through the action.

This way, Martin said, “another community along Route 66 gets to share its identity with the community at large.”

Allison Lehn of Boston participates in a caravan from Santa Monica Pier to Chicago, celebrating the centennial of Route 66.

By 11:15 a.m., Martin’s car had reached Sunset Boulevard in Silver Lake. Meanwhile, assorted other parades and caravans are traveling Route 66 in other states this year; most of them concentrate on short segments.

By 12:45 p.m., caravaners had met the mayor of Beverly Hills and rolled through West Hollywood’s Pride festivities, arriving at Grand Central Market, running slightly ahead of time.

On May 30, an estimated 3,596 classic cars joined a “Capital Cruise” on Route 66 in Tulsa, Okla., becoming a Guinness Book of World Records holder for the largest parade of classic cars, drawing an estimated 100,000 spectators and overwhelming local traffic.

In Arizona, the Williams Historic Route 66 Car Show was set for Friday and Saturday. In Texas, the Amarillo-based Texas Route 66 Festival is running Thursday through June 13.

William Cooke of Pinon Hills, left, and Sarah Jane Woodall of Tecopa, Calif., drive along Wilshire Boulevard in a 1960 Edsel Ranger Convertible as part of a Route 66 centennial caravan.

In those states and beyond, the caravan from Santa Monica will find hotels and motels in every kind of condition, vintage neon, road food, blue states, red states and purple states.

As a package of Times stories described in May, some landmarks date to the highway’s days as a scene of Depression desperation in the 1930s, others to its giddy postwar years in the late 1940s and ‘50s.

Route 66 was created in 1926 as a highway stitching together hundreds of local roads. Nicknamed “the Main Street of America” by its boosters and “the Mother Road” by John Steinbeck in “The Grapes of Wrath,” the highway inspired Bobby Troup’s song “(Get Your Kicks on) Route 66” in 1946.

But economic life along Route 66 has been precarious since the late 1960s, when interstate highways and chain hotels began stealing traffic away from the older, slower road. After Route 66 was decommissioned as a highway in 1985, about 85% of the old route remained in use, often as small-town thoroughfares, country highways and frontage roads alongside Interstate 40.

Efforts to save and rebuild the route as a historic resource began in the late 1980s and gained ground after the 2006 release of the Pixar/Disney animated features “Cars,” which tells the story of the highway’s rise and fall. In small towns such as Tucumcari, N.M., and Seligman, Ariz., the highway remains central to local identity and economy.

A vehicle in the Route 66 caravan is photographed June 6, 2026.

This year’s centennial improvements along the route “are things that are going to go into the future,” Martin said. “The real impact is going to be next year and the years after.”

Where are the best bakeries to buy celebration cakes? I want to get a cake for one of my college friends — we’ve been friends for 40 years — who is retiring from teaching kindergarten. I’m having a small brunch party for her at a restaurant in Long Beach. It’d be great if the bakery is in Pasadena or on the East Side, but I will travel for awesome cake! She loves chocolate and espresso martinis. — Roberta Tragarz

Looking for things to do in L.A.? Ask us your questions and our expert guides will share highly specific recommendations.

Here’s what we suggest:

Roberta, I think it’s so sweet that you are throwing a retirement party for your longtime friend. In my opinion, no celebration is complete without a good cake and I, too, will drive just about anywhere for one that I think the recipient would love. Here are some bakeshops that might just have “the one.”

With Pasadena being convenient for you, you’re in luck. Times restaurant critic Jenn Harris calls the city a “pastry and dessert destination.” She writes about six stellar new bakeries that have opened within a one-mile radius, including Salted Butter Company, which offers a gorgeous round cake topped with seasonal florals, and Sweet Red Peach, which can create just about any custom cake you can dream up.

Given that your friend loves chocolate, consider buying a cake from Proof Bakery in Atwater Village. The worker-owned cooperative shop used to sell a chocolate espresso cake, which would’ve been perfect because your friend loves espresso martinis. However, they swapped it out for a chocolate blueberry cake with chocolate mascarpone mousse and blueberry compote. Thankfully, it looks just as delicious. And you can still make Proof’s chocolate espresso cake at home.

No L.A. bakeshop has been recommended to me more than SusieCakes. With multiple locations spread across the county including one in Pasadena, the classic bakery makes an array of delightful desserts: old-fashioned chocolate cakes, flourless chocolate cakes, rainbow sprinkle cakes and even a cake flight so you can try all of their signature slices. Former Times food editor Amy Scattergood wrote about SusieCakes, “You can pick the flavor of cake and color of buttercream frosting, get stuff written on top, even order a pretty impressive Barbie cake (they provide the doll; the cake is the dome of her massive skirt).” A “Teacher Barbie” that looks like your friend would be adorable.

Now, this isn’t a traditional cake but hear me out. My good friend Tori Johnson had a cinnamon roll cake at her recent birthday party and I haven’t been able to stop thinking about it since. It was gooey, soft and slathered in a classic tangy cream cheese frosting. Her boyfriend got it from BadAsh Bakes, the viral bakery based in Pasadena best known for its cinnamon rolls, cookies, brownies and layer cakes. You can preorder the cinnamon roll cake, which comes in a classic, red velvet or matcha flavor.

For an eye-catching, avant-garde cake that you won’t find at a traditional bakery or grocery store, consider ordering a custom dessert from Celeste Perkins, the L.A.-born baker who makes “cakes with big personalities, for big personalities,” as Times contributor Tasbeeh Herwees writes in Image. Perkins, who works out of her home kitchen, got her start baking cakes for friends and has since made them for an array of celebrity clients including Tunde Adebimpe (frontman for the band TV on the Radio), Japanese American singer Mitski and British singer Suki Waterhouse. Not only are the cakes yummy, they are photo-worthy.

Now for some rapid-fire picks across L.A.: My colleague Jason Lew recommends Phoenix Bakery in Chinatown, specifically the strawberry cake with sliced almonds. Times Features reporter Lisa Boone also suggests Valerie Confections in Glendale. “I’ve ordered cake from Valerie several times for different occasions and they’re always really special, pretty and so good,” she says. Her favorite is the fallen fruit cake, but the bakery also sells a flourless chocolate almond cake and German chocolate cake. There’s also République, the French-inspired bakery and cafe known for its salted caramel chocolate cake. Finally, you can never go wrong with Porto’s, which sells an array of cakes including chocolate raspberry, Parisian chocolate, mango mousse, strawberry cheesecake and more.

Retiring is such a big deal, so I love to hear that you are celebrating it as such. I hope that these recommendations help you find the perfect cake for your friend. Be sure to send us a photo of the one that you choose. Have a wonderful time!

Designers Jeanine Hattas Wilson and Julie Hattas Kennedy’s magical transformation of a 4-foot-by-4-foot storage closet at this year’s Pasadena Showcase House of Design almost feels like a metaphor for design showcases themselves: not quite real, but pure fantasy.

“It was inspired by our dad, who used to read to us in Woodstock, Ill.,” Wilson says of their immersive storybook escape, which features a delightful hand-painted mural on the walls and tiny lanterns that, when touched, offer a narrated fairy tale. “We wanted to create a special, intimate space for kids.”

Showhouses are always extravagant, and this year’s event takes place inside the 8,000-square-foot former home of Clara Baldwin Stocker, daughter of land investor and racehorse breeder Elias J. “Lucky” Baldwin. Like her father, Stocker was known for her colorful personality and love of lavish things, including parties that lasted for days. (Baldwin Stocker’s 1929 obituary noted that out of her $10-million estate, about $1.5 million was jewelry, “the collection and wearing of which was her hobby.”)

Many of the 30 revamped interior and exterior spaces in the 1907 shingle-style home include details Baldwin Stocker would have loved. The Midnight Garden Dining Room by the House of Pontovi, for example, has an Italian Murano glass chandelier, feminine Art Deco-style swivel chairs with flapper-style fringe and a gold-leaf ceiling that has replaced Calico Corners fabric. The Entertainment Room by Studio Joshua features statement lighting by Los Angeles designer Jason Koharik, an 11 Ravens custom billiards table and a Champagne cooler built into the marble bar.

And the Bloom Lounge by the Art of Room Design is so large that it can accommodate several different seating areas, a game table and a hidden liquor cabinet — another nod to Baldwin Stocker, who was also known as “the Diamond Princess.”

It’s hard to decide what stands out more at the Baldwin Oaks Estate in Arcadia: the layered interiors that look ready for a shelter magazine, or the smaller spaces, like the closets, mudroom and hidden powder rooms that have been transformed into something special.

Here are a few examples of what to expect at the event, which supports youth music programs throughout Los Angeles County.

The Enchanted Room by Hattas Studios

Identical twins Hattas Wilson and Hattas Kennedy of Hattas Studios transformed a small 4-by-4-foot storage closet into a magical forest with their hand-painted mural depicting characters from stories like “Cinderella,” “The Little Mermaid” and “The Frog Prince.” A young Clara Baldwin appears with her dog, Lucky. You can touch the tiny lanterns to hear a story in each scene or simply curl up in the soft green fuzzy chair, close the velvet curtains and let your imagination wander.

Laundry and Craft Room by Arterberry Cooke Architecture

Architect Barrett Cooke turned laundry into a pleasure in this beautiful room, which doubles as a craft room outfitted with new rose-colored cabinets, playful circular Fireclay Tile, quartzite countertops and stunning views of the San Gabriel Mountains. “I straddled making it utilitarian with how beautiful it can be,” Cooke said of the local artists represented, including ceramics by Jen King, stained glass by Molly Miller, oil paintings by Lareina Holsopple and a print by local artist and Jungalow designer Justina Blakeney. “The art ties it all together.”

The vault in the Family Parlor Room by Jamie Loren Home

The family room is the only space with a television, but with a mah-jongg table, the TV hardly seems necessary. “We wanted to create a room where the family can congregate,” said designer Jamie Loren, describing the cozy parlor painted in the color Viridian Odyssey by Dunn-Edwards Paints. She also turned what used to be a gun closet into a “vault” filled with family heirlooms, including a typewriter, perfume, photos, jewelry and a flask. “This is an ode to Clara,” she said.

Powder Room by Rebecca J. Hansen Design Studio

Details make all the difference in the small powder room by Rebecca J. Hansen, who explains that both the room and the nearby vestibule are focused on mixing patterns while keeping a consistent color palette. Hansen chose patterned terra-cotta tile from Foothill Tile & Stone Co. in Pasadena for the walls, and just outside, she used wallpaper from House of Hackney with mythical animals. Brass hardware from Corston Architectural Detail, chalk pastels and bold wood trim painted a marigold color brought everything together. “It feels like I’m in a castle in England,” she said.

The second floor landing by Blue Brick Design

Designer Lara Hovanessian has transformed the foyer walls of both the first and second floors into a striking display for local artists Blakeney, Susanna Speirs Ali and Lareina Holsopple. The spaces feature the newly released Huntington Collection wall covering by Morris & Co. in the iconic Strawberry Thief motif, pink ceilings and Alberto Giacometti-style lighting from Visual Comfort.

The Mudroom by Gex Designs

Inspired by the shingles of the 1907 home, Noelle Gex Djokovich, known for last year’s playful flower-cutting room, has reimagined this space with custom cabinets, patterned floors and charming details such as a dog bed, a Lewis & Wood fabric skirt and a rag rug from Nickey Kehoe. “Adding layers to a small room makes you feel good when you come home,” she said.

The Magnolia Room by Cordrey Collection

Designer Steven Cordrey says the Magnolia wallpaper reflects his Southern roots and the Phillip Jeffries grasscloth on the walls is practical (“It’s easy to clean,” Cordrey says). He also likes to bring the outdoors in, pointing to the views of the estate’s grand oaks and pool from the second-floor bedroom. There’s a hidden touch too: Rock Zehler’s stylish dressing room, inspired by Art Deco and the 1970s, has a secret closet tucked behind a pocket door.