Get your kicks on Route 66

UNITED STATES – Traversing the historic Route 66 – the legendary “Mother Road” – is on many bikers’ bucket lists. As the route celebrates its 100th anniversary in 2026 and riding season kicks off from April to October, The Straits Times’ executive artist Jaster Ngui relives the iconic Americana road trip she took with friends in 2023, travelling from Los Angeles to Chicago over six days.

Route 66 Fast Facts

Historic highway: One of the original major highways connecting the Midwest to the West Coast.

“Mother Road”: Named by American writer John Steinbeck, it was the primary escape route for thousands of people migrating west during the 1930s Great Depression.

Pop culture: Immortalised in American entertainer Bobby Troup’s classic song (Get Your Kicks On) Route 66 (1946), the 1960s television show Route 66 and Pixar movie Cars (2006).

Road-trip culture: It is famous for its neon-lit diners, classic motels and quirky attractions that define “classic America” for travellers from around the world.

Infrastructure: In 1938, it became the first United States highway to be fully paved.

Must-sees in California

End of the Trail (Santa Monica)

The iconic sign at the Santa Monica Pier marks the end of the 3,943km journey.

Elmer’s Bottle Tree Ranch (Oro Grande)

A surreal desert forest of 200 “trees” made from vintage glass bottles by the late renowned American folk artist Elmer Long.

Roy’s Motel & Cafe (Amboy)

A popular film location, it can be seen in Hollywood movies such as The Hitcher (1986) and Kalifornia (1993), and in the music videos of American bands LANY and Queens of the Stone Age, as well as Spanish singer-songwriter Enrique Iglesias. It was built in 1938 as a petrol and service station and expanded with a cafe and motel cabins in the 1940s. Today, this spot continues to attract visitors seeking a slice of Americana in the Mojave Desert. 

Must-sees in Arizona

Hackberry General Store (Kingman)

Opened in 1930, it serves as a gift shop, visitor centre and museum. Check out its memorabilia, vintage petrol pumps and classic cars. It is a premier spot for Route 66 nostalgia. 

Roadkill Cafe/O.K. Saloon (Seligman)

A quirky diner known for its delectable menu and “you kill it, we grill it” humour. It features a themed menu with “gruesome” names such as Bambi Burger, Civet Cow and Philly Fender Tender. It actually serves American staples such as steak, barbecue, burgers and salads.

Cars of the Mother Road (Williams)

This eye-catching, quirky roadside attraction offers more than just gifts and souvenirs. It is filled with vintage cars out front. 

Standing on the Corner (Winslow)

A popular attraction celebrating the Eagles’ 1972 hit song, Take It Easy.

Wigwam Motel (Holbrook)

It is a historic Route 66 icon designed by American entrepreneur Frank Redford in the 1930s, featuring concrete teepee-shaped cabins designed to replicate sleeping in a wigwam. Seven villages were originally built – notable survivors are in Holbrook, Arizona (1937) and San Bernardino, California (1949) – serving as popular restored roadside attractions. 

Must-sees in New Mexico

El Rancho Hotel (Gallup)

The hotel served as a base for Hollywood film crews and stars. It was known as “Home of the Movie Stars” in the 1940s and 1950s for celebrity guests such as American actor John Wayne and former actor and late US president Ronald Reagan. 

Blue Swallow Motel (Tucumcari)

This nostalgic motel was featured in movies such as Back To The Future Part II (1989) and Cars (2006). Spot the iconic neon sign that lights up once the sun goes down. 

Must-sees in Texas

Midpoint Route 66 (Adrian)

The official midpoint of Route 66, it is located exactly 1,833km from both Chicago and Los Angeles. Pop by the iconic Midpoint Cafe, famous for its “ugly pie”. Flavours range from classics like apple and pecan to creative hybrids like the Elvis pie, made with chocolate, peanut butter and banana cream. 

Cadillac Ranch (Amarillo)

An interactive art installation where visitors are encouraged to spray-paint 10 half-buried Cadillacs. 

The Big Texan Steak Ranch & Brewery (Amarillo)

The Big Tex Rex statue standing at 9.2m tall is hard to miss. Established in 1960, the saloon-style steakhouse is known for its free steak challenge. Participants must consume a 2kg steak, salad, baked potato, shrimp cocktail and bread roll in one hour to earn the meal for free. There is also a souvenir store and western-themed motel on site. A perfect night’s stay after visiting the Cadillac Ranch. 

Must-sees in Oklahoma

Buck Atom’s Cosmic Curios on 66 (Tulsa)

This 6.4m-tall giant is located in a former 1950s petrol station. It served as a popular souvenir stop in Tulsa. New giants were built around the area in recent years, such as Stella Atom, Cowboy Bob, Rosie the Riveter and Meadow Gold Mack the Friendly Lumberjack.

Blue Whale of Catoosa (Tulsa)

Measuring 6.1m tall and 24.4m long, this quirky waterfront structure was built in 1972 by a zoologist for his wife and grandchildren. The attraction is closed for renovation and will reopen on May 30 in celebration of Route 66’s 100th anniversary.

Must-sees in Kansas

Cars on the Route (Galena)

The journey through Kansas on Route 66 is only about 20.9km – the shortest of all the states. A drive through the small town of Galena is a must – it looks like a movie set. The Cars on the Route attraction is a stop dedicated to Pixar’s Cars (2006).

Must-sees in Missouri

Gary’s Gay Parita (Ash Grove)

A fascinating place filled with old cars, trucks, petrol pumps and signs from the past. A perfect rest stop to grab a soda and walk around the premises.

Devils Elbow Bridge (Devils Elbow)

Built in 1923, it is a steel truss bridge in Missouri spanning the Big Piney River. The curve of the river and sharp bends in the road inspired the name “Devils Elbow”. It was restored in 2014.

Gateway Arch (St Louis)

The 192m-tall stainless-steel monument symbolises the gateway to the west. 

Must-sees in Illinois

Route 66 Association of Illinois (Pontiac)

This museum houses thousands of pieces of memorabilia from the glory days of the Mother Road.

Gemini Giant (Wilmington)

The 3D Muffler Men, also known as “giants”, were created in the 1960s to attract motorists to businesses. They became part of the Route 66 attractions over the years. Gemini Giant stands at 8.5m tall and was inspired by the National Aeronautics and Space Administration’s Gemini space programme, capturing the country’s fascination with the space race.

Chicago Begin Route 66 Sign (Chicago)

The historic sign is located at the junction of Adams Street and Michigan Avenue. This is the start of Route 66. As at March 2026, the official symbolic starting point of Route 66 in Chicago is Navy Pier, which had been moved from its historic location to mark the 100th anniversary.  

2026 centennial celebrations

California

April 21 to 27: Route 66 Bike Week at various locations.

April 30: Opening ceremony at Santa Monica Pier with live broadcasts.

Arizona

April 20 to 26: Route 66 Bike Week, featuring massive motorcycle gatherings on historic stretches.

Aug 15: Mother Road Classic Car Show in Flagstaff, showcasing vintage vehicle exhibits and music.

Sept 25 and 26: Standin’ On The Corner Festival in Winslow, inspired by American rock band Eagles’ song Take It Easy (1972), and paying tribute to Route 66 culture.

Texas

June 4 to 13: Taking place mostly in Amarillo, this celebration features 10 days of events, including concerts, car cruises and food.

Oklahoma

May 30: Tulsa’s Route 66 Capital Cruise, which will feature a large parade of classic cars.

July 24 to 26: Mustangs On The Mother Road, organised by The Mustang Club of America and hosted by the Green Country Classic Mustangs club in Tulsa.

Missouri

April 30: Local ceremonies in Springfield and St Louis include live broadcasts, concerts and public festivities.

Illinois

April 30: Opening ceremonies in Joliet include concerts and festivities.

June 20 to 28: The Route 66 Centennial Great Race is a nine-day, 3,700km vintage car rally starting in Illinois and finishing in California.

Gear up: motorcycle rentals

We use motorcycle rental company EagleRider, which offers an extensive fleet including the BMW R 1250 GS, Yamaha FJR1300 and various Harley-Davidson models.

Pro tip: We booked several months in advance to ensure availability, especially during the peak season from June to August.

Costs: Rentals average US$200 (S$255) a day. There is a one-time US$750 vehicle drop-off fee for one-way trips. The company also offers tour packages that include hotel stays.

My Ride: 2023 Harley-Davidson Heritage Classic

Engine: Milwaukee-Eight 114
Horsepower: 94 to 100.5hp
Transmission: 6-speed
Seat height: 67cm (laden)
Weight: 330kg (running order)
Fuel capacity: 18.9 litres
Features: Standard ABS, cruise control and hard-shell saddlebags