The Route 66 trail from Lebanon to Springfield, Missouri, takes you off the interstate on a winding path dotted with semi-ghost towns, old barns, vintage buildings, and a roller-coaster ride over rolling hills. A beautiful stretch of highway, this section was bypassed before I-44 was established, when a new four-lane alignment was built in 1957.
Along this quiet stretch of pavement, you will see many historical views of Route 66, roaming cattle, many tumbling buildings, and a couple of historic towns that have survived.
The first stop along this old route is Phillipsburg, which provides a peek at several vintage buildings, including what appears to be a two-story general store and a large school building.
Though the town still supports a tiny population with an active church, it is mainly filled with historic structures that speak loudly of a better era.
Beyond Phillipsburg, you continue through the rolling hills to Conway, which has fared better because of its proximity to I-44.
Conway was named after a railroad contractor and was founded by farmers who settled the area in the late 1860s. The first store opened in 1869, and the settlement slowly grew. By 1874, it had its first school in a one-room log cabin.
By 1880, the town had a new two-story building used for the school, church, and area meetings. In 1913, Conway built a tomato canning factory, and trainloads of tomatoes began shipping from the area.
When Route 66 passed through, the town boasted several businesses, including the Electric Theater, the Stone Motor Company, and a bank. Today, Conway is not a ghost town but remains a tiny community of just over 600 people.
About six miles West of Conway, look for the long-defunct Abbylee Modern Court. Surrounded by vegetation, you can barely see the sign, but the vintage court still stands, apparently renting its units as apartments.
A few more miles down the road, the tiny town of Niangua presents itself, still hanging on thanks to the influence of local farmers. Niangua, sometimes pronounced “Niangee” by the locals, also displays more vintage buildings, most of which are no longer in business, even though the town still supports over 400 residents. Signs of better times!
As you near Springfield, the highway passes from steep hills to plains and gently rolling hills. It passes through the crossroads hamlet of Strafford, which has become an almost suburb of the quickly growing city of Springfield.
Soon, you arrive in Marshfield, the county seat of Webster County. The town was laid out in 1856 and was primarily populated by local farmers and ranchers. When the Civil War began, the town saw two skirmishes. The post-war railroad boom helped the community grow as a dairy, poultry, and livestock producer.
Today, Marshfield is a rapidly growing community that supports more than 4,500 residents. It was once home to Edwin P. Hubble. The community now proudly displays a ¼ scale replica of the Hubble Space Telescope in the town square.
©Kathy Alexander/Legends of America, updated October 2026.
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