Beginning on June 6, the Main Street of America Route 66 Centennial Caravan will embark on a 2,400-mile, three-week journey from Santa Monica to Chicago, making multiple daily stops along the full stretch of the “Mother Road” in celebration of its 100th anniversary. Crossing all eight states along Route 66, the caravan will spotlight preservation success stories, while calling for the continued revitalization of landmarks and communities along the historic highway.

Organized by the Route 66 Road Ahead Partnership with support from the National Trust for Historic Preservation, the caravan will include representatives from statewide organizations dedicated to promoting and preserving Route 66. Members of the public are invited to participate for as long as they wish.

“Route 66 was main street in so many of the towns that it went through,” says Rhys Martin, manager of the Preserve Route 66 initiative at the National Trust. “We wanted to make sure that as many towns as possible on Route 66, with our event, have a moment that’s just about them.”

Here are some of the notable stops the caravan will make along the way.

To track the caravan check the live map after June 6, 2026 and follow the National Trust @preserveroute66 and @savingplaces on Instagram!

Osterman Gas Station (Peach Springs, Arizona)

On June 10, the caravan will visit the Osterman Gas Station in Peach Springs, Arizona. At the height of Route 66’s popularity, the gas station helped make the town an important stop for travelers heading to the Grand Canyon.

Built in 1929, the single-story, concrete structure is on the National Register of Historic Places and is the only surviving one of Peach Springs’ five historic gas stations. It has been owned by the Hualapai Tribe since the 2000s, and the tribe has been working to restore and preserve the landmark, along with the many stories it holds.

Charlie Vaughn, former chairman of the Hualapai Tribal Council and a current tribal council member, spent summers working at the gas station as a teenager and remembers the bustle that surrounded it. “You could hardly get around Route 66 when the station was in its heyday,”

he recalls. “You had to run to avoid the vehicles that were coming east and westbound.”

The Osterman Gas Station was included on the National Trust for Historic Preservation’s 2023 list of America’s 11 Most Endangered Historic Places. Work has already been done to repair damage to the roof and walls sustained during severe weather events in 2021 and 2023—with support provided by National Trust’s HOPE (Hands on Preservation Experience) Crew, Benjamin Moore, Historic Route 66 Association of Arizona, and other partners. The process to determine the gas station’s future public use is ongoing.

The Big Texan (Amarillo, Texas)

The Big Texan Steak Ranch in Texas, which has been welcoming diners since 1960, is one of the most recognizable stops along Route 66 with its bold neon signage and unapologetic Western aesthetic. The caravan will stop there on June 15, but the steakhouse will have a presence throughout the journey.

The Big Texan is famous for its 72-ounce steak challenge, which began in 1962 and dares patrons to devour a four-pound steak – along with a baked potato, three shrimp, a side salad, and a roll – in under an hour. During the caravan, the Big Texan will host the challenge every evening in a different town or city. Second-generation owners and brothers Bobby and Danny Lee will prepare the steaks, while local restaurants will provide the sides, adding regional flair to the iconic challenge and creating slightly different menus each evening.

“It’s a very meaningful place for a lot of people,” says Hannah Weeks, director of external affairs for the Big Texan. “We’re using the steak challenge to highlight those relationships and these iconic places on Route 66.”

Round Barn (Arcadia, Oklahoma)

On June 18, the caravan is set to stop at the Round Barn in Oklahoma, a Route 66 landmark built in 1898 by local farmer William Harrison Odor. To create the barn’s distinctive circular shape, Odor soaked native bur oak boards while they were still green, making it possible to curve them.

The structure is the only round barn along Route 66 and is listed on the National Register of Historic Places. Today, the Round Barn hosts concerts, weddings, and other events. “It’s still a community gathering point, just like it was when it was built,” says Shellee Graham, author of Route 66: The First 100 Years and a volunteer at the Round Barn.

The Round Barn represents the kind of preservation success story the caravan will tout: By the 1970s, the structure had fallen into severe disrepair, and in 1988 its roof collapsed. A dedicated group of local retirees who called themselves the “Over-The-Hill-Gang,” led by builder and carpenter Luke Robison, undertook an ambitious restoration effort that ultimately saved the beloved landmark.

Old Joliet Prison (Joliet, Illinois)

While Route 66 is synonymous with its neon signage and classic Americana charm, there are sites that serve as a reminder that the road’s history is as layered and complex as that of the nation itself. This deeper narrative is reflected in the Old Joliet Prison Historic Site in Illinois, where the caravan will stop on June 24 and celebrate a Big Texan steak challenge.

Construction of the prison began in 1858 and relied heavily on inmate labor, which involved quarrying limestone from a nearby vein. By 1878, the facility was severely overcrowded, holding more than 2,000 men. Amid calls for reform and despite notoriously inadequate conditions, it continued to operate as a prison until 2002. Following its closure, the abandoned site suffered years of vandalism until the Joliet Area Historical Museum took over operation of the site in 2017. The site has since been restored and was placed on the National Register of Historic Places in 2023.