Flying Under Radar / Roots on the Rails Flying Under Radar / Roots on the Rails

2012 Trips: Route 66 Tin Can Caravan

9/13/12-9/30/12 - DEADLINE IS SEPT. 1



You’ve heard about the legendary Fred Eaglesmith journeys... Across Canada by train in the dead of winter with Willie P. Bennett leaning out the baggage car door; up the Pacific Coast to Prince Rupert on the Rocket through the Rockies; North to Churchill, Manitoba to witness the Polar Bear migration; deep into the heart of the Silver San Juans on Roots on the Narrow Gauge; and on our own boat to Newfoundland during Hurricane Season, where we ended up on Zodiacs in the midst of the wrong bay. These are adventures outside the usual routine of life!

Now it’s Fred’s Ultimate Road Trip.... getting our kicks down the entire length of Route 66.

The TIN CAN CARAVAN is an eighteen-day voyage down the the Mother Road from Chicago to LA, led by the ultimate road dog and his entourage... be one of the vans, campers, bikes and cars following - join us for a day, a week, the whole thing (or ride the wi-fi equipped motorcoach for any or all of the four segments) over the twists, turns, bumps and bends of America’s most legendary highway.

We’ll visit grain elevators and Indian Mounds, vast underground caverns and giant ketchup bottles, Mother Jones’ grave and the Grand Canyon. We’ll hang out at biker bars and hotel ballrooms, restored brothels and famous roadhouses. We’ll eat barbeque and swap road tales around late night campfires, all in the company of some of America's most celebrated songwriters... Come for the whole tour, a week-long stretch, or just a day or two. It’s all up to you.


You get air-conditioned, wi-fi equipped motorcoach transport, with nature and cultural programs, incorrect historical facts and spurious social history dispensed freely. Lodging nightly (double occupancy; single supplements available*), at least one meal at famous (or infamous) eateries every day. Admission to all attractions, National Parks, Pueblos, etc. at which we stop. Live Music with Fred & friends daily.


  • Chicago to Santa Monica $4289.00.
    (Start afternoon 9/13, end morning 10/1).


  • Chicago to St. Louis: $989.00
    (Start afternoon 9/13, end morning 9/17)
  • St. Louis to Oklahoma City: $1,289.00
    (Start morning 9/17, end morning 9/21)
  • Oklahoma City to Albuquerque: $1,289.00
    (Start morning 9/21, end morning 9/25)
  • Albuquerque to Santa Monica: $1,489.00
    (Start morning 9/25, end morning 10/1)

*Single supplement for those desiring their own hotel room each night is $900 additional for the full trip. By segment: CHI-STL $225; STL-OKC $190; OKC-ABQ $190; ABQ-LA $325.

Questions? Drop Sarah a line at or call toll free 866-484-3669.


If you choose to drive your own vehicle -anything from a car to a motorcycle to an RV- you can purchase a Tin Can Caravan ticket for as many or as few days as you wish.... we supply a complete itinerary of the day’s journey, admission to the show that night, advice about where to camp and an entree to any late-night hang out at the campsite. Food and admission to roadside attractions is not provided unless specified. Bill Poss is doing the research to find out a sweet spot for Caravaners, the Fred bus and Bill and Tif's RV to spend each night. Fees charged by the campground or RV park are not included (what if you want to stay in a motel that night? it's all about personal choice, here).

Tickets to all dates remain on sale until noon EDT SEPT. 7. After that, Sept. 19 (Miami, OK to Tulsa), Sept. 25 (ABQ to Gallup, NM), Sept. 26 (Gallup to Winslow, AZ), Sept. 27 (Winslow to Flagstaff) and Sept. 29 (Needles to Victorville, CA) remain on sale until the day prior.

Tin Canner Tickets are available by going to our "TIN CAN CARAVAN DAY TICKETS" page. The price listed is $59 per day, but until 9/1 you can save $10 each day - just $49 per person - if you enter the discount code “CARAVAN” when purchasing tickets.

We would strongly advise Tin Canners (those traveling in their own vehicles) to purchase Jerry McClanahan’s EZ66 Guide, and we think everyone would enjoy the map series and the handbook. You can use the links below (we get a small cut of the action) to order them from Amazon, or you can check with your local bookstore.

The Itinerary So Far....

SEGMENT I: special guest ROBBIE FULKS joins us for the shows on 9/14, 15 and 16.

Thu. 9/13 - CHICAGOLAND!
We check into our hotel, the Write Inn, in the Frank Lloyd Wright District of beautiful Oak Park – a Chicago suburb, 2 blocks from the Green Line that whisks you to downtown Chicago attractions in 15 minutes. Walking tours of Wright’s historic buildings in the neighborhood are available, as well as tours of Ernest Hemingway’s childhood home. That evening, we have our kickoff show at Fitzgerald’s in Berwyn.

In the morning, our motorcoach departs for Chess Studios. Here is where many of the great Chicago blues records were cut by Muddy Waters, Howlin’ Wolf, Koko Taylor, Chuck Berry and Willie Dixon. After our tour, we head to downtown Chicago for a kickoff meal at Lou Mitchell's... at the start of The Mother Road. We travel through Wilmington to view the Gemini Giant - one of the legendary ‘muffler men’ that dot the route - this one decked out with a suspiciously welder-like spaceman’s helmet. Passing through the hamlets of Dwight and Odell, we see some classic Route 66 small towns, as well as lovingly restored vintage filling stations. We stop in Pontiac and visit the Route 66 Museum and the Pontiac Car Museum, then hop on the freeway for the short ride to Bloomington, and a show at the Six Strings club.

Mid-morning we head out from Bloomington and make our first stop in Atlanta for lunch at the beautifully restored Palms Grill - a 1930’s luncheonette - tour the only working turn-of-the-20th-century Illinois grain elevator open to the public, view the slightly menacing Bunyan Giant and stroll the town square, and climb the town clock tower where you can have a turn cranking the 1906 hand-wound Seth Thomas clock. From Atlanta, we’ll roll through Lawndale (site of the 1977 Lawndale Thunderbird Abduction - Charlie's favorite site on all of Route 66!) and proceed past Shea’s Petroliana and take a peek into the fetishistic world of vintage gas-related ephemera, then we’ll tour the Lincoln homestead - the only home Abraham Lincoln ever owned. After checking in to the State House Inn, right opposite the State Capitol in downtown Springfield, we have an opportunity to stroll, grab dinner, and then head to a show that night in Riverton.

A late-morning departure gives you plenty of time to sleep in, visit the Abraham Lincoln Presidential Library and Museum just six blocks from our hotel, or for a less-esoteric activity, you can hop a cab to the Cozy Dog Drive-In – birthplace of the corn dog. After hitting the road, we’ll stop in Litchfield at the Ariston Cafe, serving Route 66 travelers since 1924. As their neon sign says, “Remember where good food is served!” We will be passing through an area where mining once was king, and next up is Mt. Olive - and a visit to the grave of famed union leader Mother Jones (“Don’t mourn; organize!”), we’ll roll by Soulsby’s service station, and then it’s on to Staunton and Henry’s Rabbit Ranch, a totally oddball collection of actual bunnies, truck trailers and old VW’s. Next up is Collinsville, home of the giant ketchup bottle as well as the ancient native settlement now known as the Cahioka Mounds, the remains of the largest prehistoric native civilization north of Mexico. After a tour, it is but a short drive to St. Louis, where we’ll check in to the Hilton Downtown, within spitting distance of the Arch and scores of downtown restaurants and watering holes. An evening concert awaits at Off Broadway.

SEGMENT II - special guest AUDREY AULD for shows 9/17, 18, 19, 20. JON LANGFORD also shows up for 9/16, 17, 18, and then leaves on the 19 when we get to whales.

The morning is available to tour the famed Arch and the Museum of Westward Expansion, or for the rail fans among us, a visit to St. Louis’ beautifully restored Union Station. A midday departure launches us off to the famed Maramec Caverns, followed by a leisurely ramble through small towns like Cuba, Bourbon (where the water tower labeled “Bourbon” is sadly not filled with same), Fanning and its Giant Rocking Chair. We'll have a BBQ and an early show in Devil’s Elbow, Missouri (so called for a treacherous curve in the river where many a logjam occurred). From there we head to The Munger Moss Motel - a Route 66 classic - with a fire pit and impressive neon signage setting the stage for a late night jam under the stars.

In the morning, we’ll drive through Marshfield, hometown of Edwin Hubbell, and home to a 1/4-size model of the Hubbell Telescope on the courthouse lawn. We’ll visit Red Oak II, a formerly decaying early 20th century village that has been completely re-located, piece by piece and preserved in a former cornfield, stop at a couple of vintage service station/museums, and arrive late in the afternoon at the well-know “foodie” destination of Cafe on the Route in -as James McMurtry says - that “one hell-raising town” of Baxter Springs, Kansas. A private dinner and show are ours to enjoy there. That night, we’ll stay at the Indian-run motel and casino in nearby Miami ('my-AM-muh'), Oklahoma.

Wed. 9/19 - MIAMI TO TULSA, OK
If you wish, a mid-morning tour of Miami, OK’s gorgeous 1920’s sixteen-hundred seat Coleman Theatre starts the day off, followed by a stop at Afton, Oklahoma’s Packard Automobile Museum and restored DX gas station, and a cruise by Ed Galloway's Totem Pole Park, which boasts the world’s tallest concrete totem pole! We’ll enjoy lunch at Clanton’s in Vinita, OK, a roadside eatery about whose chicken-fried steak Michael Stern of Roadfood waxed rhapsodic: “beefy, crisp-crusted luxury that is ineffably amplified when it's pushed through mashed potatoes and peppery cream gravy“ before visiting the Will Rogers Memorial (“I never met a man I didn’t like”) in Claremore. Outside of Tulsa we’ll view the enigmatic Blue Whale of Catoosa, arriving in Tulsa proper in late afternoon in plenty of time for the evening music, which is a completely unplugged song circle and pickin' party (bring your guitar) hosted by Audrey Auld.

The morning is free to explore Tulsa’s unique downtown - one of the largest concentrations of art deco buildings in the country, dating from Tulsa’s part in the oil boom in the 20’s. We’ll stop for lunch at either Russ’ Ribs or the Rock Cafe - both Route 66 legends - then head to Chandler and Arcadia, past the apparently-very-one-of-a-kind Round Barn. We’ll visit the Oklahoma City Memorial late in the afternoon, and that evening, enjoy a concert at the Blue Door. Here, monster Texas songwriter Jon Dee Graham joins our merry band for the next few days to Albuquerque.

SEGMENT III - special guest JON DEE GRAHAM for shows 9/21, 22, 23, 24

We depart Oklahoma City and drive over the Lake Overholser bridge, listed on the National Register of Historic Places and on to Elk City, OK for a stop at the National Route 66 Museum and the Old Town Museum Complex to wander through the life size dioramas of motels, gas stations and other Route 66 iconography. The afternoon routes us through McLean, TX for a visit to the Devil’s Rope Barbed Wire Museum, then on through Groom to see the Leaning Tower of Groom and The Cross of Our Lord Jesus Christ (reportedly the largest cross in the western hemisphere). We end our first day in Texas in Amarillo at the Big Texan Motel and Restaurant, a shrine to Texan excess (we dare you to try the Free 72 oz. Steak Dinner Challenge). No Caravan show this night - instead, we have tickets to the Tri State Fair, where there's a rodeo and a concert by Ray Wylie Hubbard!

The morning begins with an exploration of downtown Amarillo to check out the Dynamite Museum, which is not really a museum, but the wacky public signage project of eccentric millionaire art patron Stanley Marsh 3, featuring such gems as “Road Does Not End” and “I Don’t Suppose Anyone Has A Tomato”. Then we’re off to the iconic Cadillac Ranch to make messy art on partially buried cars. Lunch time finds us at the Midpoint Café in Adrian TX, where we celebrate the halfway point of our epic journey with “Ugly Crust Pie”. We cross into New Mexico late in the day and bed down for the night in Tucumcari, a treasure trove of vintage motels and restored neon signage, TeePee curios and other delightfully kitschy attractions. If time permits, we’ll try to squeeze in a side visit to the Mesaland’s Community College Dinosaur Museum. A barbeque dinner at Tucumcari Ranch and Farm Suppy and an evening concert at the Lizard Lounge follow, and maybe a late night song circle under the beautiful neon sign of The Blue Swallow Motel.

In the morning we head to Santa Fe over the fabled Glorieta Pass - at 7,500 feet, the highest point on Route 66 - and into the storied city of the Southwest, where you’ll be free to wander the historic Plaza, visit the Georgia O’Keefe Museum, gorge yourselves on green chile cheeseburgers and stroll Canyon Road. An evening concert in the old mining town of Madrid rounds out the day.

Those who wish to spend more time in the great city of Santa Fe are welcome to do so and rejoin the group later in the day by hopping on the convenient RailRunner shuttle or driving directly to Albuquerque. Our bus, however, will be heading off of 66 for a day of exploration in the Jemez range... with a trip to Bandalier National Monument and the Valles Caldera National Preserve, where we’ll have a chance to take a short hike through this pristine wilderness before heading past Jemez Springs and down into Albuquerque where our hotel for the night sits just at the edge of historic Old Town and its myriad shops and restaurants. An evening concert - our last with Jon Dee - ensues at Low Spirits.

SEGMENT IV - special guest MARY GAUTHIER for shows 9/25, 26, 27, 28, 29, 30

We depart Albuquerque via Central Avenue and its many Route 66 landmarks, and head for a tour of Acoma Sky City, the oldest continuously inhabited community in North America, and now home to 4,800 tribal members of the Acoma Pueblo and 250 dwellings perched atop a sheer-walled 367 foot sandstone bluff. Following a tour of this remarkable historic and cultural site, we’ll have lunch, then head out to Grants, NM (briefly known as “The Carrot Capital Of The World” in the 1930s) and head to the world’s only underground uranium mining museum (if it's open) to learn about mining and the history of the regional railroad, logging and ranching industries. Late afternoon finds us pulling into the neon-bedazzled town of Gallup, NM. We figure an evening concert in the Lounge of the El Rancho Hotel is a good way to round out the day.

Departing Gallup, we’ll head past some of the most spectacularly classic southwestern tourist traps: trading posts, giant tee pees, fiberglass animals perched on the cliffs – it’s not to be believed. Then to cleanse our palates of all the tacky commerce, we’ll head to the Painted Desert/Petrified Forest National Park and see the spectacular vistas of multi-hued badlands and some of the world’s most colorful concentrations of petrified wood. We’ll stop at the Rainbow Forest Museum and a few of the more spectacular overlooks. Departing the National Park and re-joining Route 66, we’ll take a swing through Holbrook, AZ to see the impressive collection of dinosaur and petrified wood themed tourist traps, one of the very few remaining WigWam motels and end our day at the storied La Posada Hotel in Winslow, AZ, the last great Fred Harvey railroad hotel, designed by Mary Colter and rescued from ruin in the nineties by dedicated preservationists who are well on their way to restoring it to its former glory. At La Posada, we’ll enjoy a buffet dinner at the famed Turquoise Room, followed by a private concert in front of the fireplace in the La Posada Ballroom.

Those who wish to can stroll downtown to have their picture taken “standin’ on the corner in Winslow, AZ – a few blocks from the hotel. After that, we’ll head west from Winslow to just past Flagstaff, the take a detour off of Route 66 to spend the day at the Grand Canyon – how could we not? You’ll have time to explore some of the hiking trails on the South Rim, visit the Kolb Studio, have a cocktail at the majestic El Tovar and gawk at the wonder of it before we head back to the ‘real world’ for our evening concert and hotel at the (reportedly haunted) Monte Vista Hotel.

We depart Flagstaff and head west for a day of travel on the longest contiguous stretch of original Route 66 still extant... On a fine segment of gravel 66 over Fortynine Hill (the highest point on Arizona 66), then onward to Seligman, home of the Snowcap Drive-In and Angel Delgadillo's barber shop (Angel was one of the founders of the Route 66 re-birth and spearheaded the loving preservation of this iconic Route 66 town that refused to die. Then we’ll head out to Peach Springs, AZ for lunch and a tour of the Grand Canyon Caverns, where an elevator has (thankfully) replaced the hand-cranked winch that used to lower visitors down into the largest dry cavern in the US. Re-surfacing, we’ll travel further along original 66, through Peach Springs, Truxton, Valentine and then a brief stop at the Hackberry General Store. We’ll continue on through Kingman and end our day in Needles, CA (home to Snoopy’s cousin Spike) with dinner and a show at the Needles Elks Lodge.

Today we head out into the Mojave Desert. We’ll pass the restored Goffs Schoolhouse, then it’s back onto Route 66, along the “Public Art Corridor” and a collection of “shoe trees” before lunch in Ludlow. Then on to Barstow and its Mother Road and Railroad museums. We then take a swing through Oro Grande and make a stop at Elmer Long’s Bottle Tree Ranch - a shrine to ingenuity, recycling and oddly compelling art. Evening show at the Ambassador Hotel Lounge.

We rise and greet the day – our last on Route 66 – and head over Cajon Pass to San Bernadino, then through Rialto, Rancho Cucamonga, with a final stop for a celebratory lunch before we head into Los Angeles and on to our final destination and the official end of Route 66 – The Santa Monica Pier! Our final night includes a concert at McCabe's and hotel.

$300 per person non-refundable deposit to hold space. Payment plans happily accommodated. 2% discount for full payment at time of signup or if series of postdated checks are received within ten dats of signup. Payments outside of deposit are refundable until 60 days prior to departure. Reservations are transferrable. Liability release signature at time of trip check-in is required.

Sign up today, by e-mailing Roots on the Rails at or call 866-484-3669 (toll free in the US & Canada) or 802-258-1397.

The Fine Print: The payment of a deposit or any part or full payment for a reservation shall constitute consent to all the provisions contained herein. Flying Under Radar, LLC shall not be held responsible for property loss or damage and/or any damages resulting from illness, personal injuries or death which may be sustained by reason of, or while engaged on, any trip or tour whether due to the ownership, maintenance, use, operation or control of any vehicle, hotel, common carrier or any other conveyance used in carrying out these tours. We can assume no liability due to any cause whatsoever whether caused by failure or delay or other irregularity, acts or omissions occurring during a tour under which the means of transportation or other service thereby is offered or supplied by owners, operators or public carriers for whom Flying Under Radar, LLC acts only as agent. Flying Under Radar, LLC reserves the right (at its discretion) to alter or omit any part of the itinerary, or change any reservation, feature and/or means of conveyance without notice or for any reason whatsoever and without allowance or refund and with extra costs, if any, resulting therefrom paid by the passengers. Although all artists are contracted to appear, lineup is potentially subject to change due to illness or force majeure. We reserve the right to cancel any tour prior to departure, in which case payment will be refunded without further obligation on our part. Flying Under Radar, LLC shall not be responsible for any injury to person (whether or not resulting in death) or damage to property. Flying Under Radar, LLC strongly urges individual passengers to obtain appropriate insurance coverage. Baggage is at the owner's risk entirely. The transportation companies concerned are not to be held responsible for any act, omission or event during the time passengers are not aboard their carriers or conveyances. The passenger contract in use by the carriers concerned (when issued) shall constitute the sole contract between the transportation companies and the purchaser of these tours and/or passage. By accepting the ticket the passenger also agrees to its terms and conditions. By forwarding of deposit, the passenger certifies that he/she does not have any mental, physical or other condition or disability that would create a hazard for him/herself or other passengers. Flying Under Radar, LLC reserves the right to cancel or withdraw any person as a member of the tour at any time. Flying Under Radar, LLC and Roots on the Rails management reserve the right to refuse service to anyone whom it considers incompatible with the best interests of its services or its guests.