During the early heyday of Route 66, this very spot in which you’re standing—immediately east of the crossroads of Joliet Road and La Grange Road—was literal countryside. And it marked a big moment for Route 66 travelers—the exodus from the Chicago roar onto the open road heading west.

Today it’s clearly part of the Chicago metropolis but sports a unique Route 66 distinction: a rare town the Mother Road created.

Visiting Countryside

In 1946, writing in the iconic A Guide Book to Highway 66, Jack D. Rittenhouse cooed that “one of life’s biggest thrills is the realization that ‘we’re on the way.’” He’s talking about the spot where this present-day town of 6,400 is located. Countryside’s first development came a couple of decades later, and the town was finally incorporated in 1961.

A good starting point today is Illinois Harley-Davidson (9950 Joliet Road; illinoishd.com/about-us), right behind the monument. The dealer is presently expanding, and it's the place to peek at “Hogs” or get merch; they also rent bikes and offer riding classes.

You’re likely to find a bike or two outside Countryside’s enduring and endearing roadhouse Rafferty’s Irish Pub (10901 W. Joliet Rd), a popular stop for smashburgers and clam chowder since 2001. Wednesdays are karaoke nights.

Roots of Chicago Comedy?

In 1917, well before Chicago’s famed Second City opened its doors for stand-up comedians in 1959, the Marx Brothers’ family purchased a chicken farm near this spot to help the boys sidestep the WWI draft. The future comics showed little gusto for agricultural life, however.

“We got up at 5, then 6, then 7,” Groucho admitted. “Then Chico discovered that La Grange was near the Chicago Cubs ballpark. We didn’t farm anymore.”

Read about it at a plaque near the 1925 Erie steam shovel, an excavator used to extract limestone rock in nearby quarries (much of which was used to build Route 66 itself). You’ll find it outside the Local 150, on the south side of Joliet Road, just west of the La Grange intersection.

Lost Road

Route 66 today zigzags through Countryside at sudden angles. It didn’t used to be that way. After cracks in the road revealed excessive quarrying damaged it beyond repair in the late 1990s, the state closed a mile of the original Mother Road, necessitating the roundabout itinerary for 21st-century Route 66 travelers. (The dispute eventually led to a quarry operator here settling with the state out of court for $40 million.)

Nearby, peer back east where you can look over the Route 66 roadblock towards a tattered stretch of Route 66. Unfortunately, it is unlikely to reopen anytime soon.

(Read more about it in this Chicago Tribune article from 2011.)

Outdoor Activities

If you’re looking to stretch your legs, a mile south of the monument lies the serene Arie Crown Forest (La Grange Rd at 67th St; fpdcc.com/places/locations/arie-crown-forest) with more than three miles of nature trails showcasing the region’s original prairies and woodlands.

Its name honors Arie Crown, born Asie Krinsky in Minsk, who immigrated to the United States in 1883 and settled in Chicago. Today, the Crown name adorns many Chicago institutions, including the lakeside Arie Crown Theater and Ida Crown Jewish Academy, named after his wife (the park’s lake also carries her name).

Another popular place for outdoor fun is the Flagg Creek Golf Course (6939 Wolf Rd; www.flaggcreekgolfcourse.com), a beloved local course with a unique history. It originated as an 18-hole course around the time of Route 66 opening, but a highway project eventually cut it down to a true rarity in the sport: a 12-hole course. In 1993, it was refashioned as a ninehole course. There’s also a popular bar and grill here.

In the early 1920’s the Robert Henry family developed this property into an 18 hole golf course named Maple Crest. Maple Crest was not a championship facility even when it was 18 holes, but had its loyal followers. In the mid 50’s the Illinois Toll Road Authority began construction on the Tri State Tollway reducing the size of the golf course. Because of this construction Maple Crest became the only 12 hole golf course in the Chicagoland area. (Photo of this unique 12 hole course is on display in the clubhouse)

Designer Greg Martin plowed under all of Maple Crest’s 12 holes and came up with a 9 hole course that is interesting for players of all levels. There are no forced carries to scare juniors, women and seniors, but there are risks that the low handicapper can take. The course has four par 4s including the 403 yard ninth, four par 3s and the fifth hole a tricky 466 yard par 5. In 1995 and 2006 Chicagoland Golf Readers Choice Award voted Flagg Creek the number one 9 hole golf course in the area.

In the early 1920’s the Robert Henry family developed this property into an 18 hole golf course named Maple Crest. Maple Crest was not a championship facility even when it was 18 holes, but had its loyal followers. In the mid 50’s the Illinois Toll Road Authority began construction on the Tri State Tollway reducing the size of the golf course. Because of this construction Maple Crest became the only 12 hole golf course in the Chicagoland area. (Photo of this unique 12 hole course is on display in the clubhouse)

Designer Greg Martin plowed under all of Maple Crest’s 12 holes and came up with a 9 hole course that is interesting for players of all levels. There are no forced carries to scare juniors, women and seniors, but there are risks that the low handicapper can take. The course has four par 4s including the 403 yard ninth, four par 3s and the fifth hole a tricky 466 yard par 5. In 1995 and 2006 Chicagoland Golf Readers Choice Award voted Flagg Creek the number one 9 hole golf course in the area.

Flagg Creek hosts six leagues, is the home course to the high school teams, provides golf instruction, hosts several golf outings and special events each year, and boasts a lighted driving range. Stop by to hit a bucket of balls or enjoy a cold drink on the back deck overlooking the course.

More Information

Countryside hosts many interesting festivals. On the first Saturday of March, its St. Patrick’s Day Parade is capped with a bus-led “pub crawl” to various establishments around town. The Route 66 Centennial Car Show is on June 6, 2026, while another big annual draw is the Bluegrass and Brews Festival in September.

Check countryside-il.org for more information on these events and the area.