Illinois' Bustling Route 66 Stop Is Packed With Quirky Attractions, Outdoor Fun, And Historical Sites

With the iconic Route 66 turning 100 in 2026, there's no better time to visit the birthplace of the 'Main street of America' in Illinois. The roadtrippers' dream route touches on a dozen historic points in the Prairie State stretched across 300 miles, but one in particular embodies all the quirk, historical charm and adventurous spirit of the entire route.

To drive through Illinois and skip its lively capital Springfield would be a huge mistake. A treasure trove of history, Springfield is known as the home of Abraham Lincoln, but there's so much more to this understated, quaint metropolis than meets the eye.

More just than a history buff's dream, Springfield has become a must-stop on Route 66, thanks to the variety of activities available and attractions it offers. After leaving the Windy City (hopefully on a Chicago vacation), Springfield is the next major metropolis the highway passes through. It's just shy of 200 miles from the latter  — almost a 3 hour drive — and roughly an hour and a half drive away from the landmarks of St Louis. In Springfield, dining and attractions are much cheaper than in the Windy City, and the sites are classic roadtrip experiences that make traveling down Route 66 so unique.

Deserving the crown of quirkiest spot in Springfield, historic gas station turned museum Shea's is a time capsule of the bygone era of road trip travels. A labor of love from truck driver and owner Bill with his wife Helen Shea, the former Texaco and Marathon gas station was transformed into a museum in the mid-'90s, but closed in 2013. In 2024, the station museum reopened with a grant from the state of Illinois.

Once you have checked off this outdoors adventure, head to the Ace Sign Co. sign museum to learn more about the iconic Route 66 design, how it came about, and how it was immortalized in stickers, prints, and decorations across the States and beyond. The museum contains over 85 historic signs, all sporting the characteristic bright neons against painted and shaped metal plates. Before you take the next exit, make sure to pay a visit to Springfield's own muffler man — the 25-feet tall Lauterbach Giant towering above Wabash Avenue keeping a watchful eye over the municipality.

Chicago may be a dream destination for unique culinary experiences, but don't discount Springfield's lively foodie landscape. It doesn't hold a Michelin accolade, but the Cozy Dog Drive In holds a special place in local hearts and local lore. Going strong since 1949, this traditional diner claims it invented hot dogs on a stick, called 'cozy dogs.' The drive-in has the aesthetic in spades, decorated with all sorts of road trip memorabilia and the history of feeding thousands of drivers along Old Route 66.

The city's name is most commonly associated with the role it played in American presidential history. The prolific legal career of Abraham Lincoln, which paved the way for its presidency, started in Springfield, where he lived for 17 years between 1837 and 1860. An unmissable spot in the city is the Lincoln Home, restored to mirror almost identically how the president left it in 1860. Embark on a self-guided tour to learn more about the turbulent private life of the Lincoln family, including First Lady and abolitionist Mary Todd Lincoln, with whom the president raised four children. It's hard to unlink Lincoln's personal history to the city, which is filled with tributes to the 16th U.S. president, from whimsical statues of his younger days, such as the 'Rail Splitter' to more solemn, ceremonial bronzes such as the one in front of the Illinois State Capitol.

If you are keen to get back on the road, the Illinois State Fair Route 66 Experience provides you with educational tidbits and adventurous thrills inspired by roadtrippers who came before you. From billboards and a miniature drive-in theater, to old dollar notes and decorated fuel tanks, the experience is sure to be a throwback for some, and a source of interactive learning for the young ones. This self-guided attraction is open 365 days a year, and it is completely free of charge.

Save your last sunset in Springfield to park the automobile and walk leisurely along the Route 66 Mural Trail, a series of murals painted by local artists to celebrate Illinois' love for The Mother Road. The trail includes iconic local businesses, from tire shops to diners and breweries once frequented by America's original road-trippers.