Argue if you want, but we all know that 66’s goofiest roadside attractions, friendliest small towns and best pie-filled diners pop up on the eastern swath, from Chicago to western Oklahoma.
TRIP HIGHLIGHTS
5–7 DAYS
1050 miles / 1690km
GREAT FOR…
BEST TIME TO GO
May to September for extended opening hours at attractions.
ESSENTIAL PHOTO
The Gemini Giant, a fiberglass spaceman in Wilmington, IL.
BEST TWO DAYS
Oklahoma has more miles of the original alignment than anywhere, plus cowboys and chicken-fried steak.
It’s a lonely road – a ghost road really – that appears for a stretch then disappears, gobbled up by the interstate. You know you’ve found it again when a 20ft lumberjack holding a hot dog rises up from the roadside, or a sign points you to the ‘World’s Largest Covered Wagon,’ driven by a giant Abe Lincoln. And that’s just Illinois – the first of eight states on the nostalgic, kitschy, slowpoke drive west.
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1Chicago
Route 66 kicks off in downtown Chicago on Adams St just west of Michigan Ave. Before you snap the obligatory photo with the ‘Route 66 Begin’ sign (on the south side of Adams, FYI), spend some time exploring the Windy City. Wander through the Art Institute(
312-443-3600;www.artic.edu;111 S Michigan Ave;adult/child $25/free;
10:30am-5pm Fri-Wed, to 8pm Thu;
;
Brown, Orange, Green, Purple, Pink Line to Adams) – literally steps from the Mother Road’s launching point – and ponder Edward Hopper’s Nighthawks (a diner scene) and Grant Wood’s American Gothic (a farmer portrait) to set the scene for what you’ll see en route. Nearby Millennium Park(
312-742-1168;www.millenniumpark.org;201 E Randolph St;
6am-11pm;
;
Brown, Orange, Green, Purple, Pink Line to Washington/Wabash) is just plain cool, with contemporary public artworks and concerts at lunchtime and many evenings June through August.
The Drive » Stay on Adams St for 1.5 miles until you come to Ogden Ave. Go left, and continue through the suburbs of Cicero and Berwyn. At Harlem Ave, turn left (south) and stay on it briefly until you jump onto Joliet Rd. Soon Joliet Rd joins southbound I-55 (at exit 277), and you’re funneled onto the interstate.
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2 Gemini Giant
Our first stop rises from the cornfields 60 miles south of Chicago. Leave I-55 at exit 241, and follow Hwy 44 south a short distance to Hwy 53, which rolls into the town of Wilmington. Here the Gemini Giant(810 E Baltimore St) – a 28ft fiberglass spaceman – stands guard outside the Launching Pad Drive-In. The restaurant is now shuttered, but the humongous green rocket-holding statue remains a quintessential photo op.
The Drive » Get back on I-55. Take exit 154 for Funks Grove, a 19th-century maple-sirup farm (yes, that’s sirup with an ‘i’). Get on Old Route 66 (a frontage ...
