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.
This Route 66 stop is a must for quirky attractions and heaps of outdoor fun
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.
Springfield is home to astounding historical sites
