Roots on the Rails Roots on the Rails

Upcoming Trips: Dave Alvin's West of the West 2018

OCTOBER 7 - 18, 2018: 





In late March of 2018 Amtrak management announced sweeping changes on haulage of private railcars. Although final policy remains unclear, we are hopeful our original itinerary for the West of the West trip will remain largely intact. Our endpoint cities and dates (depart Los Angeles 10/7, arrive Chicago 10/11; depart Chicago 10/12, arrival back in Los Angeles on 10/17) will almost certainly remain unchanged. However the intermediate cities - and routes we travel - may have to be altered somewhat. If so, you will be kept informed of such as soon as we have definite word.

As with any of our trips - but particularly in this instance - we urge you to purchase Travel Insurance (click link here), as the situation remains very fluid.

We have operated over 45 trips with an extremely high number of returning travelers. We very much hope that you will join us for this one, current uncertainties notwithstanding. Should the trip start and end dates change, you may cancel without penalty. In a worst-case scenario, should our trip be cancelled, your monies will be returned in full.

We would appreciate it if you would contact your Congressional delegation about these changes in Amtrak policy, which we consider both shortsighted and counterproductive. Please click here for a template of a message to send.

As ever, should you have questions, feel free to call us at 802-258-1397 or shoot us an email to trains(at)

Yours for more and better music trains,
Sarah Ovenden and Charlie Hunter


  • 10/15-16 - arrive/depart Seattle (rather than Portland as per original itinerary).


To celebrate our tenth train trip with the legendary Dave Alvin, we've dreamed up something to honor the occasion in fine fashion! Join us for the full circle (your best travel value), or your choice of Eastbound or Westbound legs. Dave, Rick Shea, Christy McWilson, and an ever-changing cast of stellar musicians will be entertaining us over the course of this epic (6532 miles, to be exact!) rail journey over three of the most iconic railroad routes throughout the West. 

For most of us, the trip begins in Los Angeles with a stay at the iconic Millennium Biltmore Hotel, followed the next day with a morning departure on board our chartered private cars for the storied journey up the California coast. For those of you with other activities scheduled in the Bay Area, you can join us onboard the train in Oakland. We'll ride the staggeringly scenic California Zephyr route over the Sierra Nevadas and Donner Pass, through the Rockies to Denver, across the Great Plains to Chicago. Then westward - for a stop in the Twin Cities, then through the vast expanses of Big Sky Country, over Marias Pass in Glacier Park and the Northern Cascades to Seattle. Heading south, we travel the wide Willamette
 Valley,  climb through the rainforests of the Southern Cascades, returning to Dave's favorite landscapes of California -- from Mt. Shasta, down through the Bay Area, and culminating with a spectacular run down the Central Coast, with the Pacific Ocean crashing mere feet from the rear platform as we hurtle south to Los Angeles and a final night at the Biltmore.

Days on board the train are filled to bursting - take in as much as you'd like, or retire to your private room and watch the miles roll by. There are round-robin music 'workshops', open mics, informal song circles, concerts, nature programs, freshly-prepared meals, and an opportunity to hang out with your favorite musicians and fellow enthusiasts. Sit in the dome for unparalleled views of the American landscape. Stops in cities en route give us a chance to explore, visit museums, sample local restaurants and pubs, or whatever suits your fancy. 

This is no mass-market cruise - you'll be one of just 45 passengers on this exquisite journey. The classic streamlined railroad cars of LA Rail will be our home for the thousands of miles we will be traveling. Your host is the legendary DAVE ALVIN, accompanied by longtime sideman RICK SHEA, the incomparable CHRISTY McWILSON and an amazing lineup of musical guests. Stunningly-delicious, freshly-prepared meals and complimentary beer, wine and soft beverage service in our own 1950's-era dome car with glass-enclosed 360-degree views, plus lovingly restored sleeping cars from the golden age of streamliners make for an unforgettable travel experience. Get ready for a non-stop musical adventure.... All aboard!


DAVE ALVIN - "There are two types of folk music: quiet folk music and loud folk music. I play both," says Dave Alvin. One of the great writers and performers in American music, Dave Alvin draws from blues, country and folk traditions to make music uniquely his own. First emerging in the LA roots/punk scene as a member of The Blasters, The Flesh Eaters, and later X, Alvin has gone on to play with a veritable who's who of rock and folk, and, more recently, to forge a mighty solo career. This is his tenth Roots on the Rails trip.

RICK SHEA - "When I was younger Merle Haggard cast a long shadow, but since then Dave Alvin, Jim Ringer and a lot of other music has found its way in," says Rick Shea. Raised in San Bernadino, California, Shea's brand of storytelling cuts to the quick, and his extraordinary guitar work raises the bar even higher. He has toured as a member of Dave Alvin's Guilty Men and has become one of Roots on the Rails' most requested performers. Rick hosts the Open Mic sessions on board with grace, good humor, and top-notch honky-tonk chops.

CHRISTY McWILSON - No one is ever going to call Christy McWilson “organized.” But we love her. McWilson first made a name for herself in late-century Seattle bands the Dynette Set and the Picketts. In 2000 Dave Alvin approached McWilson with an offer to produce her first solo album, made up of her originals and a heartfelt, lovely cover of Brian Wilson's "Til I Die." The album, The Lucky One, was recorded with a core band that included Alvin, Peter Buck, and Rick Shea on guitars; Bob Glaub and Walter Singleman on bass; and Don Heffington on drums. Two years later, she called on many of the same musicians to help her put together her second solo album, Bed of Roses. This will be Christy’s fifth West of the West trip and twentieth lost pair of sunglasses.

JOHN DOE and EXENE CERVENKA - (LA-Oakland) Original members of seminal LA punk band X, John and Exene continue to also pursue independent careers, John as a singer, writer, and actor; Exene as a singer, artist and poet. John has recorded 8 solo records w/ numerous renowned singers and players, more recently including Patty Griffin, Dan Auerbach, Aimee Mann, Don Was, Kathleen Edwards and Greg Liesz. He has appeared in over 50 films and television productions, with some of his most notable roles in Road House, Georgia, Roadside Prophets, Great Balls of Fire, Pure Country and Roswell. On top of her continuing work with X, including their recent 40th-anniversary tour, Exene continues to release solo albums, and has built a critically-acclaimed body of work as a poet and mixed media artist and has published numerous volumes of poetry, essays and other writings. This will be John’s third Roots on the Rails trip and Exene’s first.

JIMMIE DALE GILMORE (Emeryville - Chicago) Jimmie has been writing and playing songs for over 50 years, blending elements of folk, country, blues, and bluegrass and defying categorization. He is a three-time Grammy nominee and was named Country Artist of the Year by Rolling Stone Magazine. Along with Joe Ely and Butch Hancock, Gilmore’s legendary band, The Flatlanders, has been credited as fathers of the Alt-country movement. This year, Jimmie and Dave are releasing their collaborative album "Downey to Lubbock" and will be touring the nation together -- but this will be your only chance to catch them on a train! This will be Jimmie’s ninth Roots on the Rails trip. We like him a lot.

LAURIE LEWIS DUO  (Emeryville – Denver) Grammy Award-winning musician Laurie Lewis is internationally renowned as a singer, songwriter, fiddler, bandleader, producer, and educator. She was a founding member of the Good Ol’ Persons and the Grant Street String Band and has performed and recorded since 1986 with her musical partner, mandolinist Tom Rozum. Laurie has twice been voted “Female Vocalist of the Year” by the International Bluegrass Music Association and has won the respect and admiration of her peers. This will be Laurie's third Roots on the Rails trip.

BLIND BOY PAXTON (Denver - St. Paul) A multi-instrumentalist in his twenties, playing music of the 1920's, Jerron "Blind Boy" Paxton channels a bygone era with astonishing range and virtuosity. You may have seen him featured in the multi award-winning music documentary AMERICAN EPIC produced by Robert Redford, Jack White & T-Bone Burnett. An utterly delightful performer, raconteur, and genuine character, Jerron joined us for his first Roots on the Rails trip in 2017, and we immediately knew we had to get him back on board.

HOWE GELB (Chicago - St. Paul) When an artist's official bio states unequivocally that he was "raised by wolves", is he really a guy you want to share close train quarters with? If we're talking about Howe Gelb, you bet! Longtime frontman for Giant Sand, and prodigious collaborator on projects ranging from producing albums by John Doe and KT Tunstall to his latest release, "Future Standards", a re-imagining of the American songbook, Gelb has explored virtually every genre of music. No matter the genre or direction he takes, his music is gorgeously illustrated with witty wordplay and vivid imagery, rendering him one of the most interesting and compelling artists at work today. We're looking forward to welcoming him on board for his first ever Roots on the Rails trip.

CAROLYN WONDERLAND (St. Paul – Seattle) Although frequently tagged with the “multi-instrumentalist” moniker, Texas native Carolyn Wonderland’s musical chops range far beyond mere technical mastery of the trumpet, accordion, piano, mandolin, and lap steel. Lauded for her searing vocals and blistering guitar work, she is one of the most powerful artists on today’s blues scene. This will be Carolyn’s first Roots on the Rails trip.

RUTHIE FOSTER (St. Paul – Seattle) Nominated for a Best Blues Album Grammy — three times in a row, recipient of seven Blues Music Awards, three Austin Music Awards, the Grand Prix du Disque award from the Académie Charles-Cros in France, a Living Blues Critics’ Award for Female Blues Artist of the Year, and the title of an “inspiring American Artist” as a United States Artists 2018 Fellow – we are looking forward to watching Ruthie Foster blow the roof off the train. Drawing from the traditions of blues, folk, soul, rock, and gospel, this vocal powerhouse imbues her music with a raw and compelling honesty and authenticity that is not to be missed. This will be Ruthie's first Roots on the Rails trip.

BILL KIRCHEN (Seattle – Los Angeles) Grammy-nominated guitarist, singer, and songwriter Bill Kirchen is one of the fortunate few who can step on any stage and elicit instant recognition. Named a “Titan of the Telecaster” by Guitar Player Magazine, he celebrates a musical tradition that embraces rock ‘n’ roll, blues and bluegrass, Texas Western swing and California honkytonk. Bill was a founding member of the legendary Commander Cody and his Lost Planet Airmen; he has released eight critically acclaimed solo albums, has toured internationally with Nick Lowe and has performed with Doug Sahm, Gene Vincent, Elvis Costello, Dan Hicks, Emmylou Harris, Bruce Hornsby and Link Wray. This will be Bill's forst Roots on the Rails trip

DEAD ROCK WEST  (Seattle – Los Angeles) Cindy Wasserman and Frank Lee Drennen make superb 'X meets Wilco' harmonic alternative country pop. Their newest recording “More Love”, produced by John Doe, is getting rave reviews for its soulful harmonies, described by the Los Angeles Times as “bent notes in tandem, musically summoning a flawless union.” This will be their second Roots on the Rails trip.


The streamlined railroad cars of LA Rail bring the golden age of rail travel back to life. These are beautifully restored vintage cars with service to match. Our cars are attached to the rear of regularly-scheduled Amtrak trains, but our cars are not accessible to ticketed passengers. There is nothing like dining high above the rails in a dome lounge car. Freshly prepared meals and complimentary beverage service (good red and white wines, Heineken on draft, vintage sodas, coffee, tea, etc.) are included in your ticket. When not in service for meals, SILVER SPLENDOR serves as our lounge space. Our performance car is the stunning OVERLAND TRAIL a 1949 Southern Pacific barbershop/lounge car, while sleepers PACIFIC SANDS, SALISBURY BEACH, and CIMARRON RIVER provide streamliner-era private cabins. 

Visit our page on different types of accommodations on board. Linens and towels are provided in all accommodations.

A cabin for two is called a BEDROOM (sometimes "Double Bedroom"), and has two chairs or a long sofa by day, converting to two bunk-style beds by night, with sink and toilet in an enclosed annex.

Accommodations for solo travelers: BERTH SPACE is a semi-private accommodation - either upper or lower (upper is accessed by short ladder) - with a wide bed with heavy curtains for privacy. Please note: should the car with berth accommodations not prove available for this trip, 'berth space' travelers will be assigned shared space in a double bedroom with a similarly gendered patron. ROOMETTES - private cabin for one, with seat by day, bed by night, and a sink in room, available to solo travelers for a supplement of $300 eastbound or westbound ($600 full-circle).


  • Prices include all onboard train activities, meals, and beverage service (soft drinks, coffee/tea, beer/wine) onboard while en route, toilet, and shower in each car, two-person occupancy of hotel rooms as noted and tickets to any land-based concerts.
  • All prices are per person. If you are traveling as a couple, please purchase two of each item.
  • For nights when hotel rooms are provided, solo travelers will be paired with a similarly-gendered patron. Solo travelers desiring single occupancy of hotel rooms can purchase solo supplements for $110.00 each night.
  •  Gratuities and other transfers not included. Liability release signature required. 
FULL CIRCLE (Los Angeles start, Los Angeles end): $8978 per person.
  • Includes hotel accommodations in Los Angeles on 10/6 and 10/17, and Chicago on 10/11.  
  • If you're joining us in Oakland, we will knock $200 per person off the fare. Please contact us directly to set up those reservations.
  • Solo travelers will be assigned berth space. Solo travelers desiring "Roomette" accommodations please purchase $600 add-on. Click here to purchase upgrade.
EASTBOUND LEG ONLY (Los Angeles start, Chicago end): $4589 per person.
  • Includes hotel accommodations in Los Angeles on 10/6, and Chicago on 10/11.  
  • Solo travelers will be assigned berth space. Solo travelers desiring "Roomette" accommodations please purchase $300 add-on. Click here to purchase upgrade.
  • If you're joining us in Oakland, we will knock $200 per person off the fare. Please contact us directly to set up those reservations.
WESTBOUND LEG ONLY (Chicago start, Los Angeles end): $ 4589 per person.
  • Includes hotel in Los Angeles on 10/17. 
  • Solo travelers will be assigned berth space. Solo travelers desiring "Roomette" accommodations please purchase $300 add-on. Click here to purchase upgrade.
  • Does not include Chicago hotel, but hotel rooms can be purchased at our group rate as an add-on (link will be posted as soon as hotel contract is set).


Reserving your space and locking in your price is pretty straightforward. You have two choices:
  • Pay all at once for maximum savings (2% off regular prices).
  • Pay your deposit now, then either pay balance within 14 days or set up a monthly automatic credit card payment.
For maximum savings, pay the FULL BALANCE ALL-AT-ONCE: 
Or pay your deposit now, then within 14 days, pay balance online or set up a monthly payment plan:
Payment Plans: Within 14 days after paying your deposit online,  if you'd prefer to set up a monthly automatic credit card payment, call us at 866-484-3669 (US/Canada only) or 802-258-1397, or email us at trains (at) to arrange. There is no additional charge for this service.

Cancellation Policy: Should you need to cancel your trip, any payments outside of deposit, and less 3% credit card fees if applicable are refundable until 60 days prior to event. Reservations are transferable to another trip up until 60 days prior to departure. Reservations are transferrable to another person right up until we print the name tags. Should we cancel this trip, monies shall be refunded in full. 


We highly recommend purchasing travel insurance for your trip. By purchasing through this link to Squaremouth (an aggregator where various insurance company policies can be compared at no additional cost to you), we receive a small commission (about five percent). This helps us keep our trips as affordable as possible. On virtually every trip we have someone who needs to cancel at the last minute due to injury or illness, family emergency, or any number of unexpected circumstances. Those who had purchased the trip insurance were disappointed to be missing the trip, but very relieved that they were not losing all the funds they had paid us, the airlines, hotels, and others. Those who did not purchase the trip insurance were really, really, sad to lose a train trip and a bunch of money too. We'd hate to see you be one of those people, which is why we stress the importance of trip insurance. Really, truly, we think it is worth it.



Saturday, October 6, 2018. Trip check-in at the Millennium Biltmore Hotel late afternoon.

Sunday, October 7, 2018: Los Angeles - Emeryville. Our private cars pull out of Los Angeles Union Station at 10:10 am and wind their way to the coast. Following a leg-stretching stop in Santa Barbara, we run along the ocean for 100 miles of unbelievable scenery, before curving in toward San Luis Obispo and the climb up over Cuesta Pass, into the vineyards and agricultural regions of Paso Robles and Salinas. Evening brings us into the Silicon Valley corridor, and then into Oakland, where we'll be joined by our Bay Area Boarders for a short (1 mile), but festive, journey into the Emeryville railyard where we'll have a late-night hootenanny and spend our first overnight on board.

Monday, October 8: Emeryville through the Sierra Nevadas. We depart Emeryville at 9:10 am, attached to the rear of Amtrak's California Zephyr, skirting the edges of the San Francisco, SanPablo, and Suisun bays, then turning inland to begin our climb up into the Sierras. We'll travel through the heart of Gold Rush Country, up to an elevation of 7,000 feet, over Donner Pass, into Nevada and through the iconic western towns of Reno, Winnemucca, and Elko -- home to the annual National Cowboy Poetry Gathering. Overnight on board across the desert.

Tuesday, October 9: Through the Rockies to Denver. The insomniacs among us can catch a brief leg stretch in Salt Lake City when we stop at 3 am, but the rest of us wake in time for a last glimpse of the red rock canyons of Utah before crossing into Colorado and beginning our spectacular climb up into the Rockies and into the indisputably most scenic section of the entire national rail network -- it is utterly fantastic! Winding through a series of remote rocky river gorges in a vintage streamliner dome car is an experience like no other. For 235 miles right outside our windows, we'll follow the Colorado River, far from the reach of highways and other human encroachment. 1,000-foot rock faces, Class V whitewater rapids, aspens, evergreens, and the occasional raft full of pantsless paddlers (it's a tradition-- they moon the train). We'll roll through Debeque, Glenwood, Gore and Fraser canyons before entering the legendary Moffat Tunnel, a 6.2-mile long feat of engineering that, when opened in 1928, cut the distance between Denver and the Pacific by 176 miles! Upon exiting the tunnel we roll down the Front Range of the Rockies and into Denver, our stationary home for the next 24 hours. Our scheduled arrival in Denver is 6:38 pm -- plenty of time to get out for a night on the town, before returning for a late night gathering onboard and another cozy night in your sleeper.

Wednesday, October 10: Denver to Omaha and beyond. With nearly a full day in Denver, we'll have a chance to explore the Mile High City, before returning to the train for our 7:10 pm departure. We head into the night and into the vastness of the Great Plains, where the legendary flatness of Nebraska affords us a great night of onboard sleeping!

Thursday, October 11: Arrive Chicago. Hotel overnight. We greet the dawn crossing the Missouri River at the Nebraska /Iowa border and spend the morning rolling across the bucolic farmland of Iowa and Illinois, then over the Mighty Mississippi, through Galesburg, the home of poet (and also folk singer/songwriter!) Carl Sandburg, and into the landscape of perhaps his best known poem, "Chicago" -- "Hog Butcher for the World, Tool Maker, Stacker of Wheat, Player with Railroads and the Nation's Freight Handler, Stormy, Husky, Brawling, City of the Big Shoulders." Our scheduled arrival at Chicago's Union Station in the early afternoon gives us plenty of time to check in to our hotel and enjoy an evening on the town on our own.

Friday, October 12: Chicago to St. Paul MN. Chicago is where the trip ends for our Eastbound travelers and where we welcome our Westbound travelers for the next leg of the journey. After a free morning in Chicago, we gather at Union Station in the early afternoon for our departure, attached to the rear of Amtrak's legendary Empire Builder. We'll pass through Milwaukee and into the region of lakes and sprawling farmland, crossing the Rock River (3 times!), through the former fur trading territories, and into the red sandstone canyons of the Wisconsin Dells. We cross the Mississippi again in La Crosse, WI and enter into Minnesota, winding through Winona and Red Wing and into our home for the evening -- St. Paul, twin city to Minneapolis and home to F. Scott Fitzgerald and railroad magnate James J. Hill. We'll be parked at the station for the next 24 hours, giving us a great opportunity to explore this great region -- the midway point between the Equator and the North Pole. Train serves as hotel for overnight stay.

Saturday, October 13: Day free in St. Paul. Evening departure westward. Our home base, Union Depot, is perfectly situated for a day of exploring the Twin Cities. The Metro Green Line light rail departs from within a block of the station and can deliver you to such noted landmarks as the Surly Brewery, home of the region's craft beer boom, a collection of great history and art museums, and the iconic Mary Tyler Moore statue. Evening finds us back on board the train for an evening concert before we are re-attached to the westbound Empire Builder and carried off toward St. Cloud, MN, the inspiration of one of the saddest songs of all time, "On a Bus to St. Cloud".

Sunday, October 14: Big Sky Country and Marias Pass. We awake in North Dakota, where the vastness of the American West engulfs us. All day and into the night we travel across this starkly beautiful landscape, through Rugby, the geographic epicenter of North America, Minot, central hub to Al Capone's Prohibition-era liquor smuggling operation, and onto the former route of the Great Northern railroad. Mid-day, we cross the Big Muddy Creek and enter into the Big Sky country of Montana and into the Fort Peck Indian Reservation. We'll travel through Wagner, scene of Butch Cassidy and the Sundance Kid's last train robbery before they hightailed it to Argentina, through the Blackfeet Indian Reservation, and by early evening we'll be climbing into the Rockies, through Marias Pass, through Glacier Park and across the Continental Divide. At times, we parallel The Danube River.

Monday, October 15: Stevens Pass and Seattle. You'll want to be sure to be up early as we climb the Cascades through Stevens Pass and Cascade Tunnel. Mid-morning, we reach Seattle. We'll be parked in the yard adjacent to King Street Station. The train serves as our downtown hotel for the evening.

Tuesday, October 16: From the valley into the Cascades. We depart Seattle in the morning, attached to the rear of the southbound Coast Starlight, and, after Portland, cross the Willamette River and up the Willamette Valley for the next 120 miles with Mt. Hood and the Cascade Range to our left, and the Coast Range on our right. In the early evening, we begin our climb through a spectacular rainforest into the Cascades, passing through 22 tunnels, to an elevation of about 5,000 feet, before reaching Klamath Falls, our last stop in Oregon before crossing into California. If the night is clear and the moon is out, we have spectacular views of Mt. Shasta off to our left.

Wednesday, October 17: Down the length of California back to Los Angeles. Morning finds us back in Sacramento where we begin to retrace our original routing southward for our final full day and evening on board. We'll skirt the bay, have a brief stop in Emeryville/Oakland, then head southward, transitioning from high tech industry to farmland, vineyards and Steinbeck country, snaking down spectacular Cuesta Grade and on to the coast, where the early evening light along the ocean serves as a fitting close to our journey. After 100 miles of unspoiled coastal views, and a stop in beautiful Santa Barbara, we head through the Los Angeles suburbs and back into "civilization" to our final stop in Los Angeles, where our comfy rooms in the Millennium Biltmore and a Singapore Sling at the Gallery Bar await!

Thursday, October 18: check out of hotel; return home.



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.