Roots Rails & Rambles Roots Rails & Rambles

Upcoming Trips: 2021 Monhegan Island, ME




"There’s a beautiful isolation on Monhegan island. A lighthouse. A cottage. An old inn. Though we are vacationers, a group of music lovers who’ve gathered there, when we walk on shore we are treated like neighbors. This is an opportunity for a special trip -- all are welcome to enjoy this magical place with us as we explore the island by day, walking on trails and bluffs to the shipwreck or the lighthouse and then gathering in the historic inn for a concert with myself and our guest artists each evening.

We've had such incredible times here over the last few years - stunning scenery, great food, drinks and music every night- all in an environment that invites relaxation, reflection and re-charging of ones' batteries. The trio this year will be Seth Glier, Susan Werner, and myself  and a very special guest we plan to announce in late March. They are dear friends and the finest musicians and songwriters you can imagine! Please join us!" - Ellis Paul

Ten miles off the formidable rocky coastline of Maine, Monhegan Island with a year-round population of 65 hardy souls, has long been welcoming painters, hikers, birders, sea kayakers, and others in search of an unplugged, scaled-back escape. Accessible only by boat (we take the mail ferry over!), Monhegan boasts no paved roads, virtually no cell signal, and a commitment to careful stewardship of its natural resources and way of life. We made our inaugural trip out there in 2018 and the island sunk its hooks into us deep! 

By day, we'll explore the rocky and uninhabited islands of Musgongus Bay, visit with local lobstering crews, connect with the artists who have claimed Monhegan as their muse and hike the miles of spectacular trails along the pristine coastline. In the evenings we'll gather for intimate, entirely acoustic, concerts - a unique opportunity to hear the music of world-class artists in its most elemental form. This event is not a songwriting instructional workshop (all are welcome whether you can sing/play a note or not), though all three artists may touch upon the art of songwriting in their informal workshops, so you'll have plenty of opportunities for gaining insight into their creative process.


Saturday, June 12, 2021: Portland, ME (optional): For those who wish to explore the wonderful city of Portland, ME, we are offering a pre-trip add-on night at a downtown Portland hotel. Portland is a delightful city with a burgeoning restaurant and arts scene. Multiple carriers service the Portland International Jetport, there's a convenient bus shuttle between Boston's Logan airport and downtown Portland and Amtrak's Downeaster train runs between Boston’s North Station and downtown Portland. We'll host an informal get-together for those arriving in Portland this evening.

CLICK HERE TO PURCHASE  add-on night of 6/12 at Westin Portland Harborview.

Sunday, June 13th: The trip officially begins. We gather and board our chartered motor coach in downtown Portland to head up the coast for a brief lunch stop in Freeport where you can also visit the flagship LLBean store and outlet (It's the law, everyone who visits Maine must stop at LL Bean). We'll continue to Boothbay Harbor of Maine's most charming harbor towns, where we'll enjoy a concert with all three artists at the historic (1894!) Boothbay Opera House and spend the night at our harborside hotel.

Monday, June 14th: We board the morning ferry for a cruise across Muscongus Bay. We’ll be traveling with the local mail, gardening supplies, lumber, fishing gear, and other ephemera of life on these outpost islands. Our journey takes us past grey seal colonies and puffin rookeries before we arrive at the Village Dock on Monhegan Island. One of the island’s few authorized pickup trucks ferries our luggage up the hill, while we take a leisurely stroll (0.3 mi) to our home for the next few days, the Monhegan House. We'll gather for a welcome dinner, perhaps some informal music around the fire, and then retire to the sounds of ocean breezes and crashing surf.

Tuesday, June 15th, Wednesday, June 16th, and Thursday, June 17th: On Monhegan Island. 

After a hearty breakfast served at the hotel each morning, you are free to structure your days as you wish. We’ll have maps of the twelve miles of hiking trails, an island gallery guide, and other resources with which to fill the day. There are yoga classes, massage, and other self-care activities available, artist’s studios and galleries to visit, a great local brewpub just a brief stroll away from our front door… and we have three full days to enjoy the island, so pace yourselves.

Each day on island we’ll be offering an activity such as seal and/or puffin watching, lighthouse tours, sea kayaking, exploring the legacy of the legendary Wyeth painting clan, and other excursions that will give you a taste of the unique history, culture, and natural environment of the region. Highlights of past visits have included  a visit to the one room Monhegan school for their end-of-year celebration for its five students (yup, all five of them!), a community contradance, a rare chance to climb up into the lighthouse, a birding walk led by local enthusiasts, a visit and presentation from a fourth generation Monhegan lobsterman with a live lobster hypnotism. 

Lunch and Dinner are on your own, with delicious options scattered around the village. Because we'll be there early in the season, not everything will be open yet, but we'll help you scout out the possibilities. The daily activity schedule has not yet been cast in stone, as much is weather-dependent, but we’re aiming for a broad selection of activities to suit a variety of interests and energy levels, with enough time built in to let the unhurried and uncomplicated pace of the island really sink in.

Ellis and the other artists will be collaborating on a songwriting workshop on one of these days (most likely the one with the dodgiest forecast), so you’ll have an opportunity to learn about and practice the craft with artists at the peak of their talents. We’ll also be building in opportunities for Open Mics (without microphones), and informal song circles around the fireplace or out on the rocks overlooking the harbor are encouraged. Bring your instruments!

Each evening there will be a full music program. These extraordinary, intimate evenings of music will showcase our guest artists unplugged in a pristine “listening room” environment. Our last night on the island concludes with a lobster dinner, with lobsters pulled right from the Monhegan waters.

Friday, June 18th: After a last breakfast at the Monhegan House and a final morning on the island, we’ll head back across the bay to New Harbor, where our bus will pick us up and take us to the stunning Pemaquid Lighthouse State Park, where we'll have a picnic lunch before heading south. If time permits, we'll squeeze in a visit to the Coastal Maine Botanical Gardens, or if the weather is uncooperative, perhaps a stop at the Maine State Prison Showroom and Store. Late afternoon finds us back in Portland where we take in an evening concert  and spend a final hotel overnight.

Saturday, June 19th: Trip participants head home.


Before purchasing your space, there a few things to make note of regarding Monhegan Island:

  •  There are no cars allowed on the island, therefore we walk everywhere. While the village is fairly compact, there are hills, dirt paths, and uneven terrain, so one should be prepared to negotiate the landscape. If needed, upon our arrival we can get you a ride from the ferry dock up the hill to the hotel. There are no elevators, and all but two rooms at the Monhegan House involve climbing some stairs.

  •  Due to water conservation efforts and delicate island plumbing, virtually all hotel rooms on Monhegan operate with shared restroom and shower facilities on each floor. The majority of rooms we have available on Monhegan for 6/14 - 6/17 all have shared restroom and shower facilities. At the Boothbay Harbor hotel on 6/13 and the Portland hotel on 6/18, all guests will have private baths.

  • A note on shared facilities: While there has been some initial trepidation about shared facilities in past years, the way Monhegan House has them organized allays any concerns about privacy or wait times. The second and third floor each have a dedicated corridor of restrooms and showers -- individual private restrooms with toilets and sinks on one side, and private shower rooms on the other. All are kept immaculately clean, well-supplied with towels, and there was never a wait. We had the hotel packed full, and it all worked beautifully.

These simple and lovely single rooms are on the 4th floor of the Monhegan House (shared bathrooms are one floor below), with the most stunning views of the island. CURRENTLY SOLD OUT, BUT CALL TO GET ON THE WAITING LIST FOR ANY OPENINGS.
DELUXE SINGLE OCCUPANCY: $3239 per person.
A lovely third floor room with double bed and shared bath. CURRENTLY SOLD OUT, BUT CALL TO GET ON THE WAITING LIST FOR ANY OPENINGS.

DOUBLE OCCUPANCY QUEEN: $2639 per person.
A lovely third floor room with Queen bed and shared bath. CURRENTLY SOLD OUT, BUT CALL TO GET ON THE WAITING LIST FOR ANY OPENINGS..

DELUXE COUPLE, $3139 per person:  Monhegan House 1st floor suite: These suites feature a queen bed, sleeper sofa, a highly-coveted private bath, and since they are on the ground floor, you'll dodge one of Monhegan's other delightfully quaint features... lack of elevators. CURRENTLY SOLD OUT, BUT CALL TO GET ON THE WAITING LIST FOR ANY OPENINGS..
DELUXE COUPLE, $3139 per person: Fish and Maine apartment: A lovely apartment suite (also with private bath and kitchen!) about 120 yards from Monhegan House. Your breakfast is included at Monhegan House. Daily housekeeping is not included with these apartments, but trash is picked up daily and supplies replenished.


ELLIS PAUL: Born a stone’s throw from the US/ Canadian border in Aroostook County, Ellis’ Maine roots run deep. A meticulous and lyrical chronicler of the times we live in and the times we’ve lived through, Ellis’ work draws deeply from the traditions of American folk music as well as his own extensive travels and experiences, spanning almost three decades of life on the road, nineteen albums, multiple awards and recognitions, and countless collaborations with other artists. He’s consistently played over 200 shows a year, at virtually every venue, festival, concert hall and coffehouse in existence and along the way has cemented his rightful place in the story of American music. 

SETH GLIER: At the relatively young age at which he finds himself, Seth has already acquired an astonishing list of accolades and accomplishments -- garnering a Grammy nomination for his sophomore record, a pair of Independent Music Awards, headlining major music festivals -- all while upholding a relentless touring schedule with the likes of Ani DiFranco and Ryan Adams, as well as  a disciplined and prolific songwriting practice. Seth's fifth and latest record, Birds, showcases the breadth and depth of his songwriter's vision, featuring terse political observations and deeply personal family storytelling.

SUSAN WERNER: With twelve albums of songs in styles ranging from folk/rock to Tin Pan Alley to gospel, country and chamber music, Susan Werner is a musical powerhouse. She is also a hoot to hang out with! A charismatic and engaging performer, Susan first arrived on the national stage when her 1995 BMG debut earned her national concert tours with Joan Armatrading and Richard Thompson.  She has performed on NPR’s World Café, NPR’s Mountain Stage, and in 2016 Nebraska Educational Television broadcast The Land Will Outlive Us All, a one hour special on Werner, agriculture, and her 2015 concert tour across the state. Her songs have been recorded by Tom Jones and Michael Feinstein, Broadway stars Betty Buckley and Christine Ebersole, and countless individuals and ensembles.


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 event 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.