Roots Rails & Rambles Roots Rails & Rambles

Upcoming Trips: 2021 Cowboy Train


Denver - Silver Plume - Canon City - Monte Vista - Antonito - Chama - Santa Fe 


Join us for a week of fellowship and authentic Cowboy culture during one of the most beautiful seasons along the Front Range of the Colorado Rockies and the stunning San Juan mountains of New Mexico. The aspens should be in full color, the scenery unmatched, and the music unforgettable! By day we'll ride the region's most scenic railroads: The Georgetown Loop, The Royal Gorge Route, and the Cumbres and Toltec and by night we'll gather for private concerts with some of the absolute best chroniclers of  the glory and complexity of the West. 
     For those who wish us to handle all the transportation, you'll ride in a comfortable chartered motor coach (with generous spacing to keep distance) each day, with frequent breaks to visit local attractions, sample local cuisine and ride some great trains!
     For those who prefer to be in charge of scheduling their own days on the road, you can choose the "Drive Yourself" option, choose the routing and stops you prefer, and join us for all the train rides, group meals and tours, and evening music and hotel stays.
     All of this with the  authentic western voices of Andy Hedges, Dom Flemons, Dave Stamey, and Brigid and Johnny Reedy as  our musical backdrop. 

We took your feedback from the last trip to heart, and have made the following adjustments: fewer hotel changes, more time to explore the environs around Santa Fe, easily accessible evening concerts at the hotels where we'll be staying (we found a great new hotel in Santa Fe with its own cabaret theater!), shorter stretches on the bus. We've factored in some new and spectacular scenery, and we threw in an additional train ride! 

Friday, September 24, 2021 - Arrive Denver. Trip check-in informal meet 'n greet, evening private concert, hotel provided in Denver. Sneak in an extra train ride by riding the Denver light rail from the airport straight to Union Station, a block and a half from our hotel.

Saturday, September 25. Day trip on chartered motor coach to Colorado Railroad Museum in Golden. This meticulously curated and maintained museum features dozens of vintage rail cars in various stages of restoration -- we can climb around inside almost all of them -- an authentic roundhouse, and fascinating railroad history exhibits. We'll let you loose in beautiful downtown Golden for lunch among its many fine eating and watering holes, then we'll head out to ride the Georgetown Loop Railroad, a classic narrow gauge steam train slicing right through the heart of the Rockies. We'll hop off mid-way to tour an old silver mine, then return to Denver for private evening concert. Denver hotel provided.

Sunday, September 26. Chartered motor coach from Denver to Canon City, with a lunch stop in Manitou Springs and Pike's Peak tour. The Pike's Peak Cog Railway has been closed for renovations for the last three years and is scheduled to re-open in May of 2021, so we may, if all things go our way, get an unexpected pandemic bonus and get to ride it to the top! Private concert and dinner (included) in Canon City with hotel overnight provided.

Monday, September 27. Lunch (included) aboard the Royal Gorge Railroad, an absolutely stunning ride on vintage streamliner equipment (with open gondola cars for amazing photography opportunities) through the jaw-droppingly gorgeous Royal Gorge, then chartered motor coach to Monte Vista, flanked by the Sawatch and Sangre de Cristo ranges,  for a private concert and dinner (included). Monte Vista hotel provided.

Tuesday, September 28. Chartered motorcoach to Antonito, where we'll board the truly epic Cumbres and Toltec Railroad for a belching steam ride through the high desert, lush meadows, and steep canyons to Chama, NM. After crossing over a 137 foot high wooden trestle, The train stops in Osier for an authentic dining hall lunch stop featuring a staggering array of homemade pies. Then we head down through Cumbres Pass, though a series of tunnels and  loops to Chama, where we're picked up by our motor coaches and whisked off to Santa Fe. A group dinner (included) and Santa Fe hotel are provided.

Wednesday, September 29. Many choices today! Those who wish can ttake the hotel shuttle right into the heart pf Santa Fe to peruse galleries shops and all the delights of this picturesque city. For those who choose, we'll be offering an ptional day trip to Santuario de Chimayo and Taos Pueblo - two sites of enormous historical and cultural importance to the region.  Private group tour of Taos Pueblo, then return to Santa Fe for private evening concert and hotel overnight.

Thursday, September 30. Another day of many choices! More Santa Fe gallery hopping, or perhaps a trip out to  Los Alamos' Bradbury Museum to learn about the work of the Manhattan Project, or we may head to Ghost Ranch, where Georgia O'Keeffe painted some of her masterpieces. We'll return to Santa Fe for private concert and hotel overnight.

Friday, October 1.  Morning shuttle service to Albuquerque airport where we bid you all a fond farewell.


ANDY HEDGES is a songster, reciter, and storyteller. His varied repertoire includes classic cowboy poetry recitations, obscure cowboy songs, dust bowl ballads, and blues. Andy taught himself to play the guitar when he was 14 and began collecting classic cowboy poems and traditional cowboy songs. He has released nine albums including four joint projects with songwriter Andy Wilkinson. He also hosts a podcast called Cowboy Crossroads, which features interviews with poets, musicians, songwriters, and historians. Both Tom Russell and Ramblin’ Jack think very highly of young Mr. Hedges, which is one of the reasons we invited him to join us for this trip, but this quote from the legendary Don Edwards really sealed the deal: "Andy could very well carry on the traditions when all us old guys are gone. I'd feel assured in knowing the music of our great American West was in good hands."

DOM FLEMONS Grammy Award Winner, Two-Time EMMY Nominee, 2020 United States Artists Fellow, Dom Flemons is originally from Phoenix, Arizona and currently lives in the Washington, D.C. area. He has branded the moniker “The American Songster” since his repertoire of music covers over 100 years of early American popular music. Flemons is a songwriter, multi-instrumentalist, producer, actor, music scholar, historian, and record collector. He is considered an expert player on the banjo, guitar, harmonica, jug, percussion, quills, fife and rhythm bones. Flemons was selected for the prestigious 2020 United States Artists Fellowship Award for the Traditional Arts category which was generously supported by The Andrew W. Mellon Foundation. He currently serves as a Governor on the Board of Directors for the Washington, D.C Chapter of the Recording Academy. In 2018, Flemons released a solo album titled “Dom Flemons Presents Black Cowboys” and received a Grammy Nomination for “Best Folk Album”. This recording is part of the African American Legacy Recordings series, co-produced with the Smithsonian National Museum of African American History and Culture in Washington, D.C.

DAVE STAMEY has been a cowboy, a mule packer, a dude wrangler, and is now one of the most popular Western entertainers working today. He has been voted seven times Entertainer of the Year, seven times Male Performer of the Year and Five times Songwriter of the Year by the Western Music Association, and received the Will Rogers Award from the Academy of Western Artists. He’s delighted audiences in twenty three states, and finds that he prefers this to being stomped by angry horses. Cowboys and Indians Magazine has called him “the Charlie Russell of Western Music.” Western Horseman Magazine has declared his “Vaquero Song” to be one of the greatest Western songs of all time. True West Magazine named him Best Living Western Solo Musician four years in a row. In November of 2016 Dave was inducted into the Western Music Hall of Fame.

BRIGID AND JOHNNY REEDY We have a special place in our heart for cowboy music and poetry phenom Brigid Reedy, because at the tender age of 4, she tagged along with her parents on our very first Cowboy Train across Canada. Little did we know what lay ahead for this pig-tailed and prairie skirted youngster!! Brigid has become a singular young voice representing her beloved home state of Montana. carrying forward classic cowboy music and poetry and rich Montana fiddle traditions with her exceptional musicianship, distinctive approach to repertoire, and her strong sense of place. Now nineteen, Brigid's writing draws considerably from her experience as a young woman coming of age in the contemporary rural West. This, combined with her timeless, eclectic taste in music and love of words, makes her a force in Western Americana music and poetry. Enter Johnny “Guitar” Reedy, Brigid's little brother, whose physical stature and musical skills belie his age. At only fourteen, Johnny has a phenomenal gift for rhythm and possesses extraordinary musical sensibilities. Transcending the role of sideman, he has become a full-fledged collaborator with his sister, assisting in arranging music for their Cowboy, Western Swing, Gypsy Jazz, and Blues repertoire. Johnny’s passion for music from around the world combined with the Montana traditions he was steeped in makes him an intriguing musical partner to his sister.


Two Trip Discount: Because we know there is a great deal of fan cross-pollination between the 2021 Cowboy Train and the Tom Russell’s Return to Texas trips, we’re offering a special deal for those who wish to have BOTH experiences. We’ve been deprived of live music and travel for a while now, so there is ground to be made up!
     If you’d like to sign up for both trips (or you’re already signed up for the Cowboy Train and would like to add on the Tom Russell "Return to Texas" trip), we’re offering a special two-trip price on each trip of $2989 per person (full trip, with motorcoach/rail transport provided) – or $2789 per person if you’d like to drive yourself/selves. call Sarah at 802-258-1397 or email her to arrange.

"Cowboy Train 2021" - Motorcoach/Rail: The full trip, with all transport provided: $3189 per person.

"Cowboy Train 2021" - Drive Yourself: Full trip, with all train rides, but you drive yourself between trip legs (Denver to Canon City, Canon City to Monte Vista, Monte Vista to Antonito, Antonito to Santa Fe, Santa Fe to Albuquerque). If you choose the drive yourself option, please be aware that riding the Cumbres and Toltec train trip requires you to leave your vehicle in Antonito, rIde the train, then take the railroad's bus shuttle (one hour) back to Antonito to pick up your vehicle (the driving distance from Antonito to Santa Fe is the same as Chama to Santa Fe - just under 2 hours). $2,989.00 per person

If you are traveling solo, we will pair you with a similarly-gendered patron, or you can purchase a solo supplement (see below) for your own hotel room each of the seven nights.


PAY IN FULL FOR MAXIMUM SAVINGS! It makes our life much easier if trips are paid in full, and we pass the savings in time and bookkeeping on to you. 2% discount off the regular price.

• Rail/Motorcoach - Pay in Full: $3125.22 per person

• Drive Yourself - Pay in Full: $2929.22 per person


If you'd rather pay a deposit to hold your space(s): $300 per person deposit. 

THEN: Within 30 days of deposit, pay your remaining balance through our online store:

Rail/Motorcoach per person balance payment: $2889  per person

Drive Yourself per person balance: $2689 per person

• or Contact Sarah at or 802-258-1397 to set up a convenient monthly credit card draw.

Solo Hotel Supplements are available at $750 per person for single occupancy of your hotel accommodations.

Credit cards (Visa, MC, Amex, Discover) and checks accepted. Payment plans at no additional charge are happily accommodated. Payment plan must be agreed upon and set up within 30 days of sign-up. Deposits, whether paid separately or as part of a full payment up front, are non-refundable, though they can be applied to a future trip with us. Liability release signature required.


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.


Our customers are extremely important to us, and when travel disruptions occur we are committed to working with you to minimize the financial impact. In the even that you need to cancel a trip for whatever reason, we will work with you to try and find a buyer for the space you are needing to give up. Often this works out great for the person needing to cancel, as they recover most of not all of their investment, and a person who might have been on a waiting list gets to go on the trip!We understand that the new realities of travel are such that we need to be more flexible than ever before. We are also an extremely small business with many fixed costs that can't be recovered once a trip is within 90 days of departure. Given that the coming months are filled with unknowns, we are proceeding ahead with confidence that we can deliver the products promised (with some reasonable degree of change when necessary), and will be completely transparent if a scheduled trip looks like it needs to be adjusted in any way that might impact your enjoyment of the experience. So please read through our cancellation policy carefully and feel free to reach out to us with any questions or concerns.

Cancellation policy: Deposits, whether paid separately or as part of a full payment up front, are non-refundable, though they can be applied to a future trip with us. Outside of deposit and credit card fees, full refund will be given up until 90 days prior to start of trip. 50% refund 60-90 days. No refund less than 60 days prior to start of trip. Reservations are fully transferable to another person.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.