A week of small museums, courthouse squares and volunteer docents across four states, from the firehouse museum in Pontiac to the two Route 66 museums of western Oklahoma.
From$3,190per person, double room
Overview
Route 66 is remembered best in the towns it passed through, and many of them keep that memory in museums run on small budgets by people who grew up there. This trip strings together a dozen of them in the order the road reaches them: the Route 66 Hall of Fame and Museum in Pontiac, the Lincoln sites of Springfield, Illinois, the state park visitor center near Eureka, the History Museum on the Square in Springfield, Missouri, and on through Carthage, Galena, Baxter Springs and Miami.
Road captain Darlene Moss worked for years as a small-town librarian in Pontiac and knows half the docents by first name, which opens a few back rooms. The pace is easy: one or two museums a day, a long lunch, a walk around a courthouse square and short drives between, never more than about 215 miles. The trip ends with the two big Oklahoma museums in Clinton and Elk City before a drive to the Oklahoma City airport.
Photos
Itinerary
Meals: B breakfast, L lunch, D dinner. Day 1 is arrival day; flights to the start are optional.
Take a cab or train from O'Hare to the hotel in the Loop, about 45 minutes. Darlene Moss meets the group at 5 pm and walks everyone two blocks to the Begin Route 66 sign on Adams Street for a first photo. Welcome dinner at a Chicago steakhouse, where she lays out the week: twelve museums, four states and about 1,050 miles of the old road, most of it on two-lane stretches.
Southwest on old 66 to Joliet and the Route 66 welcome center at the Joliet Area Historical Museum. The Gemini Giant, a fiberglass astronaut, still stands in Wilmington. Quick stops at Ambler's Texaco in Dwight and the 1932 Standard station in Odell, then two hours in Pontiac at the Route 66 Hall of Fame and Museum, in the old firehouse and city hall, where Bob Waldmire's van is parked. Dinner at the Cozy Dog Drive-In in Springfield, about 200 miles in all.
A morning for Abraham Lincoln. We tour the Lincoln Home, the only house he ever owned, then the Abraham Lincoln Presidential Library and Museum, and finish at his tomb in Oak Ridge Cemetery, where visitors rub the nose of his bronze bust for luck. After lunch, south about 100 miles to the Chain of Rocks Bridge over the Mississippi, with its 22-degree bend midstream. Frozen custard at Ted Drewes on Chippewa Street before dinner.
West out of St. Louis to Route 66 State Park near Eureka. The visitor center is in the 1935 Bridgehead Inn, a former roadhouse, with exhibits on the old road and the town of Times Beach that once stood here. On to Cuba, where a dozen murals cover downtown walls and the Wagon Wheel Motel has rented stone cottages since the 1930s. Lunch in Cuba, then about 140 miles to Springfield, Missouri, through the Ozark hills. About 215 miles in total.
Springfield calls itself the birthplace of Route 66, because the name was proposed here in 1926. The History Museum on the Square tells that story, with a Route 66 gallery and an old diner booth. Then west on the original alignment past Gary's Gay Parita, a rebuilt Sinclair station, to Carthage. We visit the Powers Museum, the town's local history museum, and walk around the 1895 Jasper County Courthouse. Night at the Boots Court Motel.
Kansas has only about 13 miles of Route 66, and we use them well. The Galena Mining and Historical Museum, in the old railroad depot, tells the story of the lead and zinc mines. Nelson's Old Riverton Store sells groceries as it has since 1925. The Baxter Springs Heritage Center covers the Civil War and the road. Across into Oklahoma for a guided tour of the Coleman Theatre in Miami and its Wurlitzer organ, then down to Tulsa, about 140 miles.
Earl Whitfield, who grew up in Clinton, joins for the Oklahoma days. Morning at Cyrus Avery Centennial Plaza, named for the Tulsa man who pushed for Route 66 in the 1920s, then the Route 66 Historical Village with its oil derrick and Frisco steam locomotive. Lunch at the Rock Cafe in Stroud and a stop at the 1898 Round Barn in Arcadia. We reach Clinton for dinner, about 190 miles from Tulsa.
At 9 am the Oklahoma Route 66 Museum opens its doors, and Earl walks the group through the decades of the road, from dirt to interstate. Then 25 miles west to Elk City and the National Route 66 and Transportation Museum, with its giant Route 66 sign and old cars. Lunch in Elk City, then about 110 miles east to Will Rogers airport in Oklahoma City, arriving by about 3:30 pm for evening flights.
Pace: RelaxedTwo to four hours on the road on most days, long stops, short level walks in towns and at roadside sights. Every stop is optional; you can always stay with the vehicle.
Route map
Map tiles © Esri, HERE, Garmin, map data © OpenStreetMap contributors. Straight lines join the stops; the trip follows the old Route 66 alignments between them.
Route at a glance
Road miles are rounded and include the detours to the stops named in the itinerary.
| Day | From and to | Miles | On the road |
|---|---|---|---|
| Day 1 | O'Hare airport to Chicago | 20 | Airport transfer |
| Day 2 | Chicago to Springfield, Illinois | 200 | Joliet, Wilmington, Pontiac |
| Day 3 | Springfield, Illinois to St. Louis | 100 | Lincoln sites, Chain of Rocks |
| Day 4 | St. Louis to Springfield, Missouri | 215 | Route 66 State Park, Cuba |
| Day 5 | Springfield, Missouri to Carthage | 70 | History Museum on the Square |
| Day 6 | Carthage to Tulsa | 150 | Galena, Baxter Springs, Miami |
| Day 7 | Tulsa to Clinton | 190 | Arcadia Round Barn |
| Day 8 | Clinton to Oklahoma City airport | 135 | Elk City museum, then east |
| Total | 8 days | 1,080 | Illinois, Missouri, Kansas, Oklahoma |
Where you stay
Rooms by town and style. The exact motels and hotels for your date, these or similar ones, are confirmed in your travel documents.
1 night
4-star hotel in the Loop near the Begin sign, or similar
1 night
Restored 1920s hotel downtown near the Lincoln sites, or similar
1 night
4-star hotel downtown near the Gateway Arch, or similar
1 night
3 to 4-star hotel close to Park Central Square, or similar
1 night
Boots Court Motel, a restored 1939 motor court, or similar
1 night
4-star hotel in the downtown Deco District, or similar
1 night
3-star hotel on Route 66 near the museum, or similar
Already included
7 nights, 7 breakfasts, 2 lunches, 3 dinners, 3 entries and guided visits
Straight talk
Dates and prices 2026-27
Per person in US dollars, sharing a double room. Group up to 14 guests.
| Dates | Status | Double roomPer person | Single roomPer person |
|---|---|---|---|
| to Sunday arrival | AvailableEarly booking: save $150 | $3,190 | $3,970 |
| to Sunday arrival | AvailableEarly booking: save $150 | $3,190 | $3,970 |
| to Sunday arrival | GuaranteedEarly booking: save $150 | $3,190 | $3,970 |
| to Sunday arrival | AvailableEarly booking: save $150 | $3,190 | $3,970 |
| to Sunday arrival | Few seatsEarly booking: save $150 | $3,190 | $3,970 |
Guaranteed means enough guests have booked and the departure will run. Seats change every week. Email [email protected] and we hold a seat for 72 hours. All departures on one page.
Optional add-on
Economy on scheduled airlines into Chicago O'Hare International Airport (ORD) and home from Will Rogers International Airport, Oklahoma City (OKC), per person including taxes. Add them when you book, or fly on your own and meet us on day 1.
Fares are held for 72 hours with your seat and confirmed when you pay the deposit. Extra nights before or after the trip on request.
Practical
Weather in Illinois
Spring is cool and showery, summer hot and humid with short storms, fall dry and mild; winter brings snow and ice
Weather in Oklahoma
Spring is mild with thunderstorm and tornado risk, summer hot and humid, fall dry and pleasant; winter brings occasional ice storms
Time zone
Central Time, with daylight saving time from March to November
Where it starts and ends
Start: Chicago O'Hare International Airport (ORD). End: Will Rogers International Airport, Oklahoma City (OKC).
What to eat
Lou Mitchell's breakfast, Dell Rhea's fried chicken, a Cozy Dog and a horseshoe sandwich in Springfield, Funks Grove maple sirup, a meal at the Ariston Cafe in Litchfield
Luggage
One medium suitcase and a small bag per person. Vintage motel rooms are compact and some have no elevator.
Your road captain
Illinois and Missouri
Darlene was a small-town librarian in Pontiac for 25 years and helped catalog the collection at the Route 66 Hall of Fame. She leads the Illinois and Missouri trip and the museums trip.
Road captains rotate on some dates; the name for your departure is in your documents. Meet all the road captains
FAQ
Booking, motels, flights and insurance questions are answered on the main FAQ page.
Between one and two hours for the larger ones, such as Pontiac, the Lincoln museum, the History Museum on the Square and Clinton, and 30 to 45 minutes at the small ones. If you want more time somewhere, Darlene can arrange to pick you up later in town.
Little. Most museums are a few steps from where the coach parks, and the longest walk is around the Lincoln sites in Springfield, about a mile on flat sidewalks. Most museums have step-free access to their main floor; tell us if you use a wheelchair and we plan around it.
Not all. Several small museums open five or six days a week and rely on volunteers. We plan each departure around their hours and call ahead. When one is closed for a holiday, we arrange a private opening or swap in a nearby site.
Yes. Oklahoma City has the National Cowboy and Western Heritage Museum and the Oklahoma City National Memorial, and we can book one or two extra nights with an airport transfer.
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