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Historic American Highways Loop

A comprehensive 16-day journey following the legendary Route 66 westward and returning via the historic Lincoln Highway. This route balances iconic Americana, neon nostalgia, and vast prairie landscapes with manageable daily driving distances.

16days
42stops
3732km

The route

Tap a day or a town

You sleep in Pontiac · Stanton · Joplin · Oklahoma City · Shamrock · Tucumcari · Santa Fe · Gallup · Winslow · Flagstaff · Moab · Glenwood Springs · Cheyenne · Lincoln · Cedar Rapids — start and end in Chicago.

DAY01

Route 66 Begin Sign → Pontiac

169 km · 1h 52m driving · Overnight in Pontiac City Hall
  1. 09:00
    Route 66 Begin Sign· start
  2. 99 km · 1h 8m
  3. 12:00
    ⭐ Gemini Giant
  4. 70 km · 44m
  5. 15:00
    Pontiac City Hall· overnight
DAY02

Pink Elephant Antique Mall → Meramec Caverns

323 km · 3h 2m driving · Overnight in Meramec Caverns
  1. 09:00
    Pink Elephant Antique Mall· start
  2. 264 km · 2h 26m
  3. 12:00
    ⭐ Gateway Arch National Park
  4. 59 km · 36m
  5. 15:00
    Meramec Caverns· overnight
DAY03

Cuba → Joplin

351 km · 3h 27m driving · Overnight in Joplin
  1. 09:00
    Cuba Murals· start
  2. 43 km · 30m
  3. 12:00
    ⭐ 66 Drive-In Theatre
  4. 308 km · 2h 57m
  5. 15:00
    Joplin· overnight
DAY04

Cars on the Route → Oklahoma City

162 km · 1h 37m driving · Overnight in Oklahoma City National Memorial
  1. 09:00
    Cars on the Route· start
  2. 12 km · 12m
  3. 12:00
    ⭐ Blue Whale of Catoosa
  4. 151 km · 1h 25m
  5. 15:00
    Oklahoma City National Memorial· overnight
DAY05

Lucille's Service Station → Shamrock

140 km · 1h 24m driving · Overnight in Shamrock Visitor
  1. 09:00
    Lucille's Service Station· start
  2. 101 km · 1h
  3. 12:00
    ⭐ Oklahoma Route 66 Museum
  4. 39 km · 24m
  5. 15:00
    Shamrock Visitor· overnight
DAY06

Cadillac Ranch → Tucumcari

227 km · 2h 7m driving · Overnight in Tucumcari Convention Center
  1. 09:00
    ⭐ Cadillac Ranch· start
  2. 163 km · 1h 31m
  3. 12:00
    Midpoint Café
  4. 64 km · 36m
  5. 15:00
    Tucumcari Convention Center· overnight
DAY07

Blue Hole → Santa Fe

93 km · 56m driving · Overnight in Santa Fe Plaza
  1. 09:00
    ⭐ Blue Hole· start
  2. 93 km · 56m
  3. 12:00
    Santa Fe Plaza· overnight
DAY08

Old Town Albuquerque → Gallup

281 km · 2h 40m driving · Overnight in Gallup Cultural Center
  1. 09:00
    ⭐ Old Town Albuquerque· start
  2. 104 km · 1h 3m
  3. 12:00
    Continental Divide Marker
  4. 177 km · 1h 37m
  5. 15:00
    Gallup Cultural Center· overnight
DAY09

Petrified Forest National Park → Winslow

217 km · 2h 4m driving · Overnight in Winslow
  1. 09:00
    ⭐ Petrified Forest National Park· start
  2. 186 km · 1h 44m
  3. 12:00
    Wigwam Motel
  4. 31 km · 20m
  5. 15:00
    Winslow· overnight
DAY10

Meteor Crater → Heritage Square

98 km · 1h 3m driving · Overnight in Heritage Square
  1. 09:00
    Meteor Crater· start
  2. 42 km · 29m
  3. 12:00
    ⭐ Walnut Canyon National Monument
  4. 57 km · 34m
  5. 15:00
    Heritage Square· overnight
DAY11

Wupatki National Monument → Moab

49 km · 36m driving · long drive · Overnight in Moab
  1. 09:00
    Wupatki National Monument· start
  2. 49 km · 36m
  3. 12:00
    ⭐ Moab· overnight
DAY12

Colorado National Monument → Glenwood Springs

195 km · 2h 1m driving · Overnight in Glenwood Springs
  1. 09:00
    ⭐ Colorado National Monument· start
  2. 195 km · 2h 1m
  3. 12:00
    Glenwood Springs· overnight
DAY13

Ames Monument → Cheyenne

364 km · 4h 8m driving · Overnight in Cheyenne Depot Museum
  1. 09:00
    Ames Monument· start
  2. 364 km · 4h 8m
  3. 12:00
    ⭐ Cheyenne Depot Museum· overnight
DAY14

Great Platte River Road Archw… → Lincoln

511 km · 4h 33m driving · long drive · Overnight in Lincoln City Hall
  1. 09:00
    ⭐ Great Platte River Road Archway· start
  2. 511 km · 4h 33m
  3. 12:00
    Lincoln City Hall· overnight
DAY15

The Durham Museum → Cedar Rapids

428 km · 4h 10m driving · Overnight in Cedar Rapids
  1. 09:00
    ⭐ The Durham Museum· start
  2. 95 km · 55m
  3. 12:00
    Lincoln Highway Bridge
  4. 334 km · 3h 15m
  5. 15:00
    Cedar Rapids· overnight
DAY16

Mississippi River Lookout → Grant Park

124 km · 1h 27m driving
  1. 09:00
    Mississippi River Lookout· start
  2. 124 km · 1h 27m
  3. 12:00
    ⭐ Grant Park
Booking timeline
Book these before you go
  1. Day 1Stay in Pontiac · Night 1
  2. Day 2Stay in Stanton · Night 2
  3. Day 3Stay in Joplin · Night 3
  4. Day 4Stay in Oklahoma City · Night 4
  5. Day 5Stay in Shamrock · Night 5
  6. Day 6Stay in Tucumcari · Night 6
  7. Day 7Stay in Santa Fe · Night 7
  8. Day 8Stay in Gallup · Night 8
Heads Up
  • Day 11: 5h 14m driving — plan rest stops
  • Day 14: 6h 25m driving — plan rest stops
  • Many Route 66 segments are disconnected; follow brown historic markers to stay on the original path.
  • Check weather conditions when crossing the Texas Panhandle and Kansas plains for high winds.
  • Book vintage motels in advance as popular spots like the Blue Swallow fill up months ahead.