Midway Between St. Louis And Springfield On Historic Route 66 Is An Illinois City Brimming With Vintage Charm

There's no road trip route quite like Route 66. Stretching from Chicago to California, the endearingly nicknamed "Mother Road" delivers neon nostalgia and kitschy Americana for over 2,400 epic miles across the U.S. Though the historic highway is one of the spectacular cross-country journeys through America's most iconic sites – peppered with illustrious cities like St. Louis and Tulsa – it's the hidden gem destinations along the way that sparkle the brightest. The heart of Route 66 is in its smaller towns, while the lonely stretches of highway leading to them are the veins that pump them full of life.

Comfortably nestled between St. Louis and Springfield, one of these small, hidden gem destinations is Carlinville, Illinois. Dating back to 1839, the historic town is famous for its local institutions like the Macoupin County Courthouse and Blackburn College. However, its connection to Route 66 is what really put it on the map. Back in 1926 (the year the Mother Road was born), the route ran right through Carlinville. Though a realignment in 1930 sent the road east to Litchfield, Route 66 left an indelible mark on the town in the form of roadside motels, historic diners, old gas stations, and vintage theaters. If you're embarking on a stunning and storied road trip down Route 66, be sure to make a prolonged pit stop in Carlinville to experience an abundance of retro charm.

If you're traveling the highway from east to west, you'll arrive in Carlinville about an hour after departing Springfield, Illinois. Start your visit here by visiting the Route 66 marker at the intersection of Nicholas and Broad Street, which will give you a good overview of the sites and stops in town. Next, head to 615 N. Broad Street to snap a selfie with the "Welcome to Carlinville" mural, whose letters frame classic scenes depicting luminaries like Abraham Lincoln, and the iconic road sign.

Making your way to the town's main square, take note of the brick paving, which is part of the original Route 66 alignment. At the time of its construction in the early 1900s, this material was used due to its affordability, availability, and ease of installation. If you're curious, about 30 miles north near Auburn, you'll find the longest brick road segment of the highway, a well-preserved piece of the historic road that stretches 1.4 miles.

Back in Carlinville, the red brick-paved streets are lined with a treasure trove of historic buildings to explore. Built in 1870, the Loomis House (known as the St. George Hotel since the 1920s) towers over the east side of the square. Stroll over to 228 W. Main Street to see the Marvel Theatre's vintage marquee. Opened in 1920, the classic movie house burned down the year Route 66 was built (reopening in 1928), and still screens films today. Nearby on the corner of W. Main Street and S. Locust, you'll see an old, single-service Phillips 66 gas station circa the 1920s. Though you can't fill up there today, the cottage-style station is a charming piece of Route 66 history.

Retro diners are among the many classic staples of Route 66. Though it relocated to nearby Litchfield in 1929, Carlinville is the site of the original Ariston Cafe. Set in one of the town's oldest buildings (built in 1854), the local diner opened in 1924 and served Route 66 travelers driving through Carlinville before the highway's realignment. You can still see the building today; however, if you want to eat at the Ariston Cafe, you'll have to travel about 17 miles east to its current location. As the oldest continually-operating restaurant on the iconic highway, serving up hearty Western-inspired entrees and sandwiches with a side of Americana charm, it's definitely worth the short trek.

Another vintage landmark in Carlinville is the Diane Drive-In. Opened in 1952, the outdoor theater operated until 1981, welcoming as many as 300 cars to enjoy movies on its screen. Today, its once neon-lit marquee stands at 1950 N and Colt Road, a slowly decaying relic of Route 66's roadside cinema past.

If you're staying the night in Carlinville, you'd be remiss not to check into a classic roadside motel. Proudly serving Route 66 travelers since the mid-century, the Carlinvilla Motel offers cozy rooms with nostalgic furnishings, as well as coffee and breakfast muffins in the morning to jumpstart your day of Route 66 kicks.