Route 66 Is The Go-To Choice For A Retirement Road Trip For One Crucial Reason

Aside from senior discounts and never-ending weekends, one of the main perks of retirement is having more freedom to travel. When it comes to choosing a destination, there's quite literally a world of possibilities. While some may opt to explore another country such as Italy, rated the top travel destination for new retirees in 2025, others choose to explore the uncharted territory in their own backyard with a stunning and storied U.S. road trip.

Though there are plenty of unforgettable routes to choose from, like California's striking, beach- and city-filled Highway 1, there's no journey quite as legendary as Route 66. Gleaming with retro diners, neon-lit motels, roadside attractions, and historic landmarks, embarking down the nearly 100-year-old route is like taking a drive down memory lane. It's no wonder that it remains a popular road trip destination among the newly-retired, especially those celebrating their 66th birthday. 

Commonly featured on lists of top retirement road trip destinations, Route 66 is so popular that it has entire social media groups dedicated to it. On Facebook, the Historic Route 66 group is flooded with posts from older members sharing and asking for travel recommendations for the famous cross-country journey. A majority of the posts emphasize Route 66's retro charms. Sparking memories of family road trips and brimming with music and memorabilia from the mid-20th century, there's one crucial reason why the Mother Road continues to beckon to older generations with its welcoming, two-lane embrace: Nostalgia.

Stretching over 2,400 miles from Chicago to Santa Monica, Route 66 is packed with attractions across the eight states it crosses. For retirees seeking the ultimate vintage vacation along the historic highway, one of the best ways to experience it is through its roadside stops. Lined with kitschy landmarks, the trip is best-suited for enjoying at a leisurely pace, rather than racing to reach the finish line — which is perfect if you don't have a job to hurry home to.

Among the most unique roadside attractions standing (very) tall on Route 66 are the "Muffler Men." Built in the 1960s and 1970s, the oversized fiberglass statues were designed to promote everything from car parts to fast food. Aesthetically inspired by Paul Bunyan, the mighty statues are scattered along the route, their muscular arms outstretched to hold different objects. Traveling east to west, the first of the Muffler Man you'll encounter is the Gemini Giant in Wilmington, Illinois — a 30-foot-tall astronaut carrying a silver rocket. Farther down the route in Atlanta, Illinois, stands an unnamed Muffler Man cradling a giant hot dog. In total, more than 20 Muffler Men dot Route 66, symbolizing a time when road trips were punctuated by gimmicky attractions designed to lure weary travelers off the highway.

Other larger-than-life objects along Route 66 include the "World's Largest Catsup Bottle" in Collinsville, Illinois, the "World's Tallest Gas Pump" in Sapulpa, Oklahoma, and the "World's Second Largest Rocking Chair" in Fanning, Missouri. When it comes to Route 66: The bigger, the better.

Aside from the kitschy roadside attractions, one of the best ways to bite into the nostalgia on Route 66 is to visit a retro diner. Decked out with vintage memorabilia, black-and-white checkered floors, red vinyl booths, and jukeboxes spinning classic '50s tunes, these old school eateries are the bread and butter of the Mother Road and are generously scattered throughout every state along the route.

Though it would be nearly impossible to stop at every diner on Route 66, each state has its highlights. In Braidwood, Illinois, the Polk-A-Dot Drive In serves up  classic '50s vibes, complete with statues of Elvis and Marilyn Monroe out front and quarter-operated jukeboxes at each table. Farther south in Springfield, Illinois, the Cozy Dog Drive-In claims fame as the birthplace of the original hot dog on a stick (basically a corn dog). In Stroud, Oklahoma, a quirky and hidden gem along Route 66, the Rock Café has been a mainstay since 1939 and even inspired the Pixar film "Cars." On the western end of the route, Peggy Sue's 50's Diner in Yermo, California, dating back to 1954, is a stunning example of programmatic architecture, featuring a jukebox-shaped entrance and burgers named after 1950s icons such as James Dean and Buddy Holly.

At the end of a long day's drive, there's no better place to take a nostalgic snooze back in time than a classic roadside motel. Hundreds line the route, but neon-lit highlights include the Blue Swallow Motel in Tucumcari, an underrated pit stop bursting with vintage charm, and Hotel El Rancho in Gallup, New Mexico, an artsy Route 66 gem with red rock beauty. Between the roadside motels, retro diners, and kitschy attractions of yesteryear, it's no wonder that retirees love to get their kicks on Route 66.