John Woodruff, an entrepreneur from Springfield, Missouri, teamed up with Cyrus Avery, the chairman of the Oklahoma Department of Highways (also known as the “The Father of Route 66”), and together they mapped out the Mother Road’s diagonal course. In 1925, Congress enacted a law for national highway construction that made Route 66 possible. On April 30, 1926 a telegram was sent from Springfield’s Colonial Hotel—demolished in 1997—proposing that the road from Chicago to Los Angeles be named Route 66. It is for this reason that Springfield is recognized as the birthplace of Route 66.

route 66 plaque in Springfield

66th Anniversary Commemorative Plaque in Springfield, MO. Photo © Tony Hisgett, licensed CC BY 2.0.

1926-1935 Alignment

Unless you have a serious time constraint, stop here: Springfield is too rich in Route 66 history to be missed.Route 66 had several realignments through Springfield. The 1926-1935 alignment enters Springfield from the northeast to run west along East Kearny Street (Hwy. 744) and continues south along Glenstone and National Avenues to St. Louis Street, which leads downtown to the Public Square.

If you don’t have much time but still want to take the 1926-1935 alignment through Springfield, cross I-65 and follow Kearny Street (Hwy. 744) west for 2 miles and turn left (south) onto Glenstone Avenue (Business 44). Drive two miles south and turn right (west) on St. Louis Street, which turns into Park Central as it wraps around the square. West of the square, the road turns into College Street and joins the West Chestnut Expressway (Business 44). Turn left (west) and keep straight as you leave Springfield. After crossing under I-44, the Chestnut Expressway turns into Highway 266.

Post-1936 Alignment

The post-1936 alignment bypasses downtown Springfield via Highway 744 west and U.S. 160 south. Unless you have a serious time constraint, stop here: Springfield is too rich in Route 66 history to be missed.

Sights in Springfield, MO

Route 66 Information Visitor Center

Say hello to the friendly folks at the Route 66 Information Visitor Center (815 E. St. Louis St., 417/881-5300, 8am-5pm Mon.-Fri.). They have a wealth of information about Route 66, along with fun souvenirs, brochures, maps of Springfield, and a replica of a 1950s diner, gas station fuel pump, and phone booth.

Downtown Springfield is just a few blocks west of the visitor center. There’s plenty of parking, so you can get out, stretch your legs and stroll the boutiques, sidewalk cafes, art galleries, nightclubs, restaurants, and theaters.

Woodruff Building

The large building on the northwest corner of Park Central East and Jefferson Avenue is the Woodruff Building (E. St. Louis St.). It was owned and named after John Woodruff, the man who established the U.S. Highway 66 Association in 1926. It was also the area’s first skyscraper and received much public acclaim and excitement when it opened in 1911. (Only 10 stories tall, it was a big deal at the time.) Route 66 ran in front of the building. Inside were offices, a pool hall, a barbershop, and two elevators. The building sold for $700,000 a few years after Route 66 began, and an additional 23,000 square feet were added in 1959.

Gillioz Theatre

Next door to the Woodruff Building is the Gillioz Theatre (325 Park Central E., 417/863-7843), which opened in 1926. An enthusiastic audience cherished the lavish Spanish Colonial Revival architecture, with terra cotta tiles, terrazzo flooring, and a grand Wurlitzer. Maurice Earnest Gillioz financed and built the theatre using primarily steel and concrete; wood was only used for the doors and handrails. An arched, stained-glass window, a recessed oculus in the ceiling, decorative urns, plaster friezes, and winged cherubs added to the opulence. As suburban strip malls became more popular in the 1970s, fewer people spent time downtown, and the Gillioz fell into disrepair before closing in 1980. Eventually, a group of locals formed the Springfield Landmarks Preservation Trust and rehabilitated and restored the Gillioz to reopen in 2006. Today, the venue hosts acts ranging from comedian Kathy Griffin to country music singer Dwight Yoakam.

Gillioz Theatre

Gillioz Theatre in Springfield, MO. Photo © Chad Thomas, licensed CC BY 2.0.

Wild Bill Shootout

It was at 100 Park Central Square that Wild Bill Hickok shot Davis Tutt in the heart over a gambling debt in 1865—the nation’s first recorded quick-draw shootout. Tutt drew first, but Wild Bill had a better aim; this incident solidified Hickok’s reputation as a serious gunfighter. A small plaque in front of the Park Central Library (128 Park Central Square) commemorates the duel, and there are street markers where Hickok and Tutt stood.

Birthplace of Route 66 Roadside Park

In 1947, Red Chaney thought it might be easier for customers to drive up and order his $0.25 burgers through a kitchen window rather than relying on a waitress or carhop. This original idea made Red’s Giant Hamburg possibly the first drive-through restaurant in America.

The unusual business name was the result of Red’s famous sign. The sign was shaped like a cross—the word “Giant” was horizontal, while the word “Hamburger” lay vertical (the two words shared an “A” in the middle). However, Chaney had to saw the “er” off of “Hamburger” once he realized the sign was too tall and would touch the power lines. The unusual spelling didn’t affect the business. In fact, it made it almost a religious rite of passage for locals and Route 66 travelers.

Unfortunately, Red’s closed in 1984. The building was removed, but a replica of the “Giant Hamburg” sign lives on at the Birthplace of Route 66 Roadside Park (1200 Block W. College St., 24 hours, free).

World’s Largest Fork

Almost five miles south of downtown is the World’s Largest Fork (Noble & Associates building, 2155 W. Chesterfield Blvd., 24 hours). The fork stands 35 feet tall and weighs 11 tons, sticking out of a patch of greenery at a slight angle. Colorado also claims to have the world’s largest fork sculpture, but either way this is a fun photo op. From downtown, take Highway 13 south toward U.S. 60.

Cave Coral in Fantastic Caverns.

Cave Coral in Fantastic Caverns. Photo courtesy of Fantastic Caverns.

Fantastic Caverns

About five miles north of Springfield is America’s only drive-through cave, Fantastic Caverns (4872 North Farm Rd. 125, 417/833-2010, 8am-4pm daily Nov.-Feb., 8am-6pm daily Feb.-Mar. and Sept.-Oct., 8am-7pm daily Mar.-Apr. and Aug.-Sept., 8am-8pm daily Apr.-Aug., $23.50). You can no longer drive your own car through the cave; instead, a jeep tram with a long wagon takes visitors to see fluted draped stalactites, stalagmites, and flowstones. The creepiest thing about this cave, however, is that the Ku Klux Klan once conducted secret meetings and cross burnings in the cave’s “grand ballroom” in the 1920s.

From College Street (Route 66) turn right (north) on Highway 13. Turn left (west) on West Farm Road. 94 and follow it as it turns south and then west to North Farm Road 125. Turn right (north) and drive about a mile.

Springfield Route 66 Eats

In 1940, David Leong came to the United States from China; Leong opened Springfield’s Leong’s Tea House in 1963. Once he saw how much the locals worshipped fried chicken, he decided to modify the already established cashew chicken dish from a stir-fried version to a deep-fried remix slathered with oyster sauce and sprinkled with green onions. It was a hit.

By the 1970s, Leong’s Cashew Chicken was served throughout the city in every type of restaurant–from diners to school lunch cafeterias. Leong’s Tea House closed in 1997 and was replaced by Leong’s Asian Diner (1540 W. Republic Rd., 417/887-7500, 11am-10pm Mon.-Sat., 11am-8pm Sun., $8-16). Even though you can find Springfield-style cashew chicken throughout the city, Leong’s uses the original recipe.

Back on Route 66

Depart Springfield via West College Street, heading west. When West College Street joins West Chestnut Expressway (Business I-44), turn left (west) and keep straight until you cross I-44 as the road turns into Highway 266. The drive west to Carthage is particularly scenic, with rolling hills and romantic reminders of what Route 66 looked like almost 80 years ago.


Excerpted from the First Edition of Moon Route 66 Road Trip.