July 29, 2026

206. Route 66 Part 1 - Chicago to Oklahoma City - From Chicago's Edge to Oklahoma's Dusty Dreams

Show Notes
Transcript

206. Route 66 Part 1 - Chicago to Oklahoma City - From Chicago's Edge to Oklahoma's Dusty Dreams guides you along the first unforgettable stretch of America’s Main Street, blending history, food, and practical travel tips for road-trippers. We start at the iconic Route 66 Begin sign at Adams & Michigan in Chicago, cruise past the Gemini Giant in Wilmington, and dig into a Cozy Dog corn dog in Springfield before soaking up the Gateway Arch and the Chain of Rocks Bridge in St. Louis and snapping photos at the Blue Whale of Catoosa. Highlights include these five stops plus hidden two-lane segments, classic diners and neon motels. Travel tips cover best seasons (spring and fall), how to navigate GPS vs. old maps, where to gas up for long rural stretches, and when to reserve museum tours. Expect recommendations for barbecue in St. Louis, pie and malt shops in small towns, and offbeat roadside attractions that make Route 66 a bucket-list drive. This episode was prepared with the assistance of AI tools, giving us more time to travel and bring you even more destinations. Travel Is Back -- over 200 episodes covering destinations across America and beyond.

Some episodes use AI for research, writing assistance, and occasional voiceover when Johnny Mac is unavailable. His point of view, and his insistence on finding the best local taco remains entirely human.

WEBVTT

1
00:00:00.080 --> 00:00:01.919
Hey, we made it to Root sixty six Part one,

2
00:00:02.080 --> 00:00:05.080
Chicago to Oklahoma City. Let's get this road trip started

3
00:00:05.120 --> 00:00:07.919
by kicking off in the windy city itself, Chicago. Now,

4
00:00:07.919 --> 00:00:09.720
before you hit the road, it's worth spending a bit

5
00:00:09.759 --> 00:00:12.439
of time exploring what Chicago has to offer. You're going

6
00:00:12.439 --> 00:00:14.439
to want to take a stroll down Michigan Avenue, also

7
00:00:14.480 --> 00:00:18.280
known as the Magnificent Mile. This place is packed with shops, eateries,

8
00:00:18.320 --> 00:00:20.960
and some of the city's most iconic architecture. If you're

9
00:00:21.000 --> 00:00:23.679
a fan of deep dish pizza, stop by Lou Malnades

10
00:00:23.760 --> 00:00:27.399
or Giordano's for a slice or four of that cheesy goodness.

11
00:00:27.480 --> 00:00:30.199
Trust me, you won't regret it. Once you're fueled up

12
00:00:30.239 --> 00:00:32.240
and have had your fill of city vibes, it's time

13
00:00:32.280 --> 00:00:35.079
to start your journey on the Mother Road. You'll find

14
00:00:35.119 --> 00:00:37.560
the official starting point of Route sixty six at the

15
00:00:37.560 --> 00:00:40.719
intersection of Adams Street and Michigan Avenue. It's a humble

16
00:00:40.759 --> 00:00:43.119
beginning for such a legendary road, marked with a small

17
00:00:43.159 --> 00:00:45.719
sign that's a must for a quick photo op. As

18
00:00:45.759 --> 00:00:48.640
you drive out of Chicago, the urban landscape gives way

19
00:00:48.679 --> 00:00:51.719
to the more laid back scenery of Illinois. Your first

20
00:00:51.759 --> 00:00:54.799
stop should be the charming little town of Joliet. Here

21
00:00:54.920 --> 00:00:58.000
you can visit the rialto Square Theater, a stunning example

22
00:00:58.039 --> 00:01:01.960
of nineteen twenties architecture that's still hosting shows today. If

23
00:01:01.960 --> 00:01:04.599
you're lucky, you might catch a local performance or just

24
00:01:04.680 --> 00:01:08.079
admire it's grandiose inside. Don't forget to check out the

25
00:01:08.239 --> 00:01:11.280
Joliet Area Historical Museum for a bit of context about

26
00:01:11.319 --> 00:01:14.719
the area's rich history. Continuing down the road, you'll pass

27
00:01:14.760 --> 00:01:18.359
through Wilmington, home to the iconic Gemini Giant. It's a

28
00:01:18.359 --> 00:01:22.439
classic Root sixty six landmark, a towering fiberglass statue of

29
00:01:22.439 --> 00:01:25.359
a spaceman that stands outside the launching pad drive in,

30
00:01:25.680 --> 00:01:28.439
perfect for a quirky photostop and a quick bite if

31
00:01:28.480 --> 00:01:31.480
you're feeling peckish. A bit further south, you'll come to

32
00:01:31.519 --> 00:01:34.319
the town of Pontiac. This place is a goal mine

33
00:01:34.319 --> 00:01:37.959
for Root sixty six enthusiasts. Visit the Root sixty six

34
00:01:38.000 --> 00:01:40.480
Hall of Fame and Museum, where you can dive deep

35
00:01:40.519 --> 00:01:43.760
into the lore and legends of this historic highway. There's

36
00:01:43.799 --> 00:01:46.920
also a fantastic collection of murals throughout the town that

37
00:01:47.000 --> 00:01:49.599
make for a great walking tour. Each one adds a

38
00:01:49.640 --> 00:01:52.000
splash of color and tells a story about the area's

39
00:01:52.000 --> 00:01:54.400
history and connection to the road. If you're in the

40
00:01:54.439 --> 00:01:56.959
mood for something a bit different, swing by the Pontiac

41
00:01:57.000 --> 00:02:00.959
Oakland Automobile Museum. It's a must for car enthusiast, showcasing

42
00:02:00.959 --> 00:02:04.519
a wonderful collection of classic and antique cars. Pontiac is

43
00:02:04.560 --> 00:02:06.319
one of those places where you'll want to linger a

44
00:02:06.319 --> 00:02:09.560
little longer, soaking in the nostalgia and the small town charm.

45
00:02:09.800 --> 00:02:13.199
As you keep cruising, you'll eventually reach Springfield, the capital

46
00:02:13.240 --> 00:02:16.719
of Illinois. It's most famous as Abraham Lincoln's hometown, and

47
00:02:16.759 --> 00:02:18.840
you can learn all about him at the Abraham Lincoln

48
00:02:18.879 --> 00:02:23.360
Presidential Library and Museum. This interactive museum does a fantastic

49
00:02:23.439 --> 00:02:26.560
job bringing history to life with its exhibits and presentations.

50
00:02:27.159 --> 00:02:29.800
While you're in Springfield, make sure to visit Lincoln's Home

51
00:02:29.879 --> 00:02:33.000
National Historic Site to see where the iconic president lived.

52
00:02:33.039 --> 00:02:36.159
Before heading to the White House for a bite to eat,

53
00:02:36.360 --> 00:02:38.960
head over to Cozy Dog Drive In, where they claim

54
00:02:39.000 --> 00:02:41.439
to have invented the corn dog on a stick. It's

55
00:02:41.439 --> 00:02:43.360
a fun stopping point and a good place to stretch

56
00:02:43.400 --> 00:02:47.560
those legs while enjoying a true American snack. Leaving Springfield behind,

57
00:02:47.680 --> 00:02:49.800
you're on your way to the next state. But before

58
00:02:49.800 --> 00:02:52.039
you cross into Missouri, make a quick detour to the

59
00:02:52.039 --> 00:02:54.960
town of Staunton to see Henry's Rabbit Ranch. It's a

60
00:02:55.000 --> 00:02:57.840
quirky roadside attraction where you can meet live rabbits and

61
00:02:57.879 --> 00:03:01.240
see a collection of Volkswagen rabbits. It's weird, it's wonderful,

62
00:03:01.280 --> 00:03:03.360
and it's exactly the kind of place that makes Root

63
00:03:03.400 --> 00:03:06.919
sixty six so special. Crossing into Missouri, you'll find yourself

64
00:03:06.919 --> 00:03:09.199
in the vibrant city of Saint Louis. Take some time

65
00:03:09.240 --> 00:03:12.039
here to explore the Gateway Arch. Standing at an impressive

66
00:03:12.159 --> 00:03:14.479
six hundred and thirty feet, the arch is the tallest

67
00:03:14.479 --> 00:03:16.560
man made monument in the United States. You could take

68
00:03:16.560 --> 00:03:18.520
a tram ride to the top for breathtaking view of

69
00:03:18.520 --> 00:03:21.240
the city and the Mississippi River. While in Saint Louis,

70
00:03:21.280 --> 00:03:23.319
you also have to try some of the local barbecue.

71
00:03:23.719 --> 00:03:26.840
Pappy Smokehouse is a favorite among both locals and visitors.

72
00:03:27.319 --> 00:03:29.360
The ribs there are legendary and might just be the

73
00:03:29.400 --> 00:03:32.840
best you've ever had. After good meal, wander around the

74
00:03:32.840 --> 00:03:35.120
del Mar Loop and eclectic neighborhood with a great mix

75
00:03:35.159 --> 00:03:38.000
of shops, restaurants, and live music venues. It's a lively

76
00:03:38.039 --> 00:03:40.479
place with a youthful energy, perfect for an evening stroll.

77
00:03:41.120 --> 00:03:43.319
Leaving the urban sprawl of Saint Louis, you'll start to

78
00:03:43.319 --> 00:03:46.120
see the rolling hills and lush forests of the Ozarks.

79
00:03:46.159 --> 00:03:48.120
It's a beautiful drive as you make your way toward

80
00:03:48.159 --> 00:03:51.479
the town of Cuba, Missouri. Known for its outdoor murals,

81
00:03:51.520 --> 00:03:55.360
Cuba celebrates its history through vibrant art that lines the streets.

82
00:03:55.400 --> 00:03:57.879
Stop by the Wagon Wheel Motel, one of the oldest

83
00:03:57.879 --> 00:04:00.800
continuously operating motels on Root sixty six, for a taste

84
00:04:00.840 --> 00:04:05.479
of vintage Americana. Continuing west, you'll pass through Rolla and Lebanon,

85
00:04:05.639 --> 00:04:08.400
offering more of that small town charm that's so characteristic

86
00:04:08.439 --> 00:04:11.599
of Root sixty six. In Lebanon, the Root sixty six

87
00:04:11.680 --> 00:04:15.120
Museum inside the local library is worth a visit. It's small,

88
00:04:15.159 --> 00:04:17.920
but packed with memorabilia and stories that capture the spirit

89
00:04:17.959 --> 00:04:20.839
of the road. As you approach the border with Kansas,

90
00:04:20.879 --> 00:04:23.319
make a quick stop in the town of Joplin, Missouri.

91
00:04:23.399 --> 00:04:25.920
This town is known for its Root sixty six drive

92
00:04:25.959 --> 00:04:28.480
in theater. If you're there in the warmer months, it's

93
00:04:28.480 --> 00:04:30.439
a perfect spot to catch a movie under the stars,

94
00:04:30.800 --> 00:04:34.000
a quintessential part of American road culture. Crossing into Kansas,

95
00:04:34.079 --> 00:04:36.800
Root sixty six only runs for thirteen miles, but every

96
00:04:36.800 --> 00:04:39.720
inch is packed with sites. The town of Galina is

97
00:04:39.759 --> 00:04:42.399
a highlight home to cars on the route, a former

98
00:04:42.560 --> 00:04:46.439
Canotech service station. Here you'll meet Toe Tighter, the tow

99
00:04:46.439 --> 00:04:50.079
truck that inspired the character Mater from Pixar's Cars. It's

100
00:04:50.079 --> 00:04:52.160
a whimsical stop that's sure to bring a smile to

101
00:04:52.199 --> 00:04:56.079
your face. Onward into Oklahoma, you'll find Quapaw, where the

102
00:04:56.199 --> 00:04:58.399
road starts to open up into the sweeping plains that

103
00:04:58.519 --> 00:05:01.839
characterize much of the state. Miami, Oklahoma is next, offering

104
00:05:01.839 --> 00:05:05.079
the Coleman Theater, a beautifully restored vaudeville theater that still

105
00:05:05.120 --> 00:05:07.759
hosts performances. It's worth stopping by for a tour or

106
00:05:07.800 --> 00:05:09.519
even to catch a show if you time it right.

107
00:05:09.920 --> 00:05:12.360
As you drive further into Oklahoma, you'll soon reach the

108
00:05:12.360 --> 00:05:14.720
town of Claremore, where you can visit the Will Rogers

109
00:05:14.839 --> 00:05:19.279
Memorial Museum. Will Rogers was a beloved humorist and social commentator,

110
00:05:19.279 --> 00:05:21.680
and the museum does a terrific job of celebrating his

111
00:05:21.759 --> 00:05:25.079
life and work. Continuing on the road takes you through Tulsa.

112
00:05:25.120 --> 00:05:27.639
Here you're going to want to dive into the thriving

113
00:05:27.759 --> 00:05:31.079
art scene. The Philbrook Museum of Art, housed in a

114
00:05:31.160 --> 00:05:35.319
stunning Italian Renaissance villa, boasts an impressive collection. Tulsa's Blue

115
00:05:35.319 --> 00:05:38.160
Dome District is another must visit, with its vibrant nightlife

116
00:05:38.160 --> 00:05:41.160
and eclectic eateries. For a taste of local cuisine, try

117
00:05:41.160 --> 00:05:43.920
some chicken fried steak at Tally's Good Food Cafe, a

118
00:05:43.959 --> 00:05:46.879
retro diner that's been serving up classic American dishes since

119
00:05:46.959 --> 00:05:50.079
nineteen eighty seven. Leaving Tulsa, you start to get that

120
00:05:50.160 --> 00:05:53.519
sense of wide open spaces as you head towards Oklahoma City.

121
00:05:54.000 --> 00:05:56.439
Along the way, make a pit stop and stroud at

122
00:05:56.439 --> 00:05:59.920
the Rock Cafe. This historic eatery has been serving roots

123
00:06:00.000 --> 00:06:02.959
sixty six travelers since nineteen thirty six and inspired the

124
00:06:03.079 --> 00:06:06.879
character Sally Carrera in Pixar's Cars. Their menu is full

125
00:06:06.879 --> 00:06:09.680
of comfort food classics, perfect for keeping you fueled on

126
00:06:09.720 --> 00:06:12.399
your journey. As you make your final approach into Oklahoma City,

127
00:06:12.439 --> 00:06:15.000
you'll pass through the town of Arcadia. Here, you can't

128
00:06:15.040 --> 00:06:18.040
miss the round Barn, a unique piece of Prairie architecture

129
00:06:18.040 --> 00:06:20.399
that dates back to eighteen ninety eight. Just down the

130
00:06:20.480 --> 00:06:23.240
road is Pops, a modern twist on the classic diner

131
00:06:23.279 --> 00:06:25.879
with a giant soda bottle out front. They offer over

132
00:06:25.920 --> 00:06:28.000
seven hundred types of soda, so it's a fun place

133
00:06:28.000 --> 00:06:30.600
to grab a drink and stretch your legs. Finally, you

134
00:06:30.720 --> 00:06:34.000
roll into Oklahoma City, the heart of Oklahoma, known for

135
00:06:34.040 --> 00:06:36.759
its cowboy culture and rich Western history. It's a city

136
00:06:36.759 --> 00:06:39.399
that offers a bit of everything. Head to Bricktown, a

137
00:06:39.519 --> 00:06:42.040
vibrant entertainment district where you can walk along the canal,

138
00:06:42.160 --> 00:06:44.519
enjoy a meal, or catch a live show. The National

139
00:06:44.519 --> 00:06:47.319
Cowboy and Western Heritage Museum is also a highlight, offering

140
00:06:47.360 --> 00:06:49.480
a fascinating look into the history and culture of the

141
00:06:49.519 --> 00:06:52.800
American West. As the day winds down, reflect on the

142
00:06:52.839 --> 00:06:56.319
journey so far. You've traveled through bustling cities, charming towns,

143
00:06:56.360 --> 00:06:59.000
and wide open spaces, all while tracing the path of

144
00:06:59.120 --> 00:07:02.480
history itself. Root sixty six is more than just a road.

145
00:07:02.720 --> 00:07:05.360
It's a living, breathing piece of Americana that tells the

146
00:07:05.399 --> 00:07:08.040
story of the places and people that make this country unique.

147
00:07:08.120 --> 00:07:09.959
And there you have it the first leg of Root

148
00:07:10.000 --> 00:07:13.319
sixty six from Chicago to Oklahoma City. We've had quite

149
00:07:13.360 --> 00:07:16.199
the adventure, and there's so much more road ahead. As

150
00:07:16.240 --> 00:07:18.000
you rest up and get ready for the next stretch,

151
00:07:18.120 --> 00:07:20.639
keep that sense of wonder and excitement. The Mother Road

152
00:07:20.680 --> 00:07:22.839
is full of surprises and every mile has a story

153
00:07:22.839 --> 00:07:24.439
to tell. But before you put your feet up for

154
00:07:24.480 --> 00:07:26.920
the night, there's still a bit more of Oklahoma City

155
00:07:26.959 --> 00:07:29.759
to explore. You're in the heart of Cowboy Country, after all,

156
00:07:29.879 --> 00:07:32.720
and the adventure is just beginning. If you're still hungry,

157
00:07:32.759 --> 00:07:34.720
you might want to check out a local favorite like

158
00:07:34.759 --> 00:07:39.040
Cattleman's Steakhouse in the Stockyard City district. It's an Oklahoma

159
00:07:39.079 --> 00:07:42.160
institution that's been around since nineteen ten, serving up some

160
00:07:42.240 --> 00:07:45.519
of the best steaks you'll ever taste. Imagine biting into

161
00:07:45.519 --> 00:07:49.279
a perfectly cooked ribbi, the flavors rich and satisfying as

162
00:07:49.279 --> 00:07:51.839
you take in the rustic, old school ambiance that feels

163
00:07:51.879 --> 00:07:55.079
like stepping back in time. Once you've had your fill,

164
00:07:55.199 --> 00:07:58.240
take a stroll through the Stockyard City area. The smell

165
00:07:58.279 --> 00:08:00.600
of leather and hay wafts through the and you can

166
00:08:00.600 --> 00:08:04.199
almost hear the echoes of cattle drives from long ago. Here,

167
00:08:04.240 --> 00:08:07.120
the streets are lined with Western ware shops and saddle shops,

168
00:08:07.120 --> 00:08:08.879
places where you can pick up a pair of cowboy

169
00:08:08.879 --> 00:08:11.439
boots or a hat to complete your look. Even if

170
00:08:11.439 --> 00:08:13.519
you're just window shopping, there's a unique charm to the

171
00:08:13.560 --> 00:08:15.720
area that makes it worth the visit. For a touch

172
00:08:15.720 --> 00:08:18.319
of culture, consider heading over to the Oklahoma City Museum

173
00:08:18.360 --> 00:08:22.800
of Art. It's right downtown and houses an impressive collection

174
00:08:22.839 --> 00:08:25.879
that spans centuries and continents. One of the highlights is

175
00:08:25.920 --> 00:08:28.600
the stunning glass work by Dale Chi Hully, a feast

176
00:08:28.639 --> 00:08:31.360
for the eyes with its vibrant colors and intricate designs.

177
00:08:31.480 --> 00:08:33.320
Walking through the exhibits, you get a sense of the

178
00:08:33.440 --> 00:08:37.519
creativity and artistic talent housed within these walls, a perfect

179
00:08:37.519 --> 00:08:40.399
counterpoint to the rugged Western landscapes you've been rolling through.

180
00:08:40.639 --> 00:08:42.279
If you're in the mood to wind down with some

181
00:08:42.320 --> 00:08:45.120
local tunes, pop over to the Jones Assembly. It's a

182
00:08:45.120 --> 00:08:47.600
lively spot that offers live music and a great selection

183
00:08:47.679 --> 00:08:50.919
of drinks and food. The atmosphere is relaxed yet buzzing,

184
00:08:51.000 --> 00:08:54.120
with both locals and travelers enjoying the night. Sit back,

185
00:08:54.200 --> 00:08:56.600
sip on a craft cocktail, and let the music wrap

186
00:08:56.639 --> 00:08:58.840
around you. It's a perfect way to end your day,

187
00:08:58.960 --> 00:09:01.279
soaking in the warm Oaklahoma night and reflecting on the

188
00:09:01.360 --> 00:09:04.399
journey so far. As the evening wraps up, make sure

189
00:09:04.440 --> 00:09:07.120
to take a moment to appreciate the Oklahoma City skyline,

190
00:09:07.159 --> 00:09:10.120
maybe from the rooftop of Vast, a restaurant located on

191
00:09:10.159 --> 00:09:13.080
the forty ninth floor of the Devin Tower, watching the

192
00:09:13.120 --> 00:09:15.320
city lights twinkle below. It's easy to feel a sense

193
00:09:15.320 --> 00:09:18.679
of accomplishment. You've driven hundreds of miles, pass through towns

194
00:09:18.679 --> 00:09:20.960
big and small, each with its own story and charm.

195
00:09:21.279 --> 00:09:23.559
You've tasted foods you might never have thought to try,

196
00:09:23.720 --> 00:09:26.799
seen sights that pictures can't quite capture. Tomorrow, the road

197
00:09:26.840 --> 00:09:29.960
beckons again, ready to lead you further west into new adventures.

198
00:09:30.000 --> 00:09:33.240
But for now, let the experiences of the day settle in.

199
00:09:33.320 --> 00:09:36.000
Oklahoma City has given you a taste of the frontier spirit,

200
00:09:36.279 --> 00:09:38.919
a reminder of the grit and determination that built the

201
00:09:38.960 --> 00:09:41.320
American West. As you drift off to sleep, you might

202
00:09:41.320 --> 00:09:43.759
find yourself dreaming of the road ahead, eager to see

203
00:09:43.759 --> 00:09:46.159
what the next leg of Root sixty six has in store.

204
00:09:46.600 --> 00:09:49.600
Rest well, because the Mother Road waits just outside your door,

205
00:09:49.720 --> 00:09:51.440
ready to take you on the next chapter of this

206
00:09:51.559 --> 00:09:55.960
extraordinary journey. I'm Johnny Mack and Travel is Back. Follow

207
00:09:56.000 --> 00:09:58.559
Travelers Back wherever you listen to podcasts, and find all

208
00:09:58.600 --> 00:10:00.960
two hundred plus destinations in our back Catalog

206. Route 66 Part 1 - Chicago to Oklahoma City - From Chicago's Edge to Oklahoma's Dusty Dreams

Listen On

Featured Episodes

Recent Episodes