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Upcoming Trips: 2022 Monhegan Island, ME with Ellis Paul, Vance Gilbert & Molly Venter

Photo credits: Benjamin Williamson/Laurie McCallister

ROOTS ON THE ROCKS 2022: with Ellis Paul, Vance Gilbert, and Molly Venter

June 12 - 18, 2022

"There’s a beautiful isolation on Monhegan. 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 Vance Gilbert, Molly Venter, and myself -- 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, limited 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 class (all are welcome whether you can sing/play a note or not), though all three artists certainly touch upon the art of songwriting in their informal workshops, so you'll have plenty of opportunities to gain insight into their creative process. No, this is a trip of relaxation and reprieve, a chance to journey to a very special place with extraordinary friends; a trip to give one strength during trying times. 

For the foreseeable future, participation in any of our trips will require proof of full Covid- 19 vaccination – that means providing us with documentation that you have received the full schedule of vaccines and boosters that meet the standards for travel in both your country of origin, and the country you’ll be visiting. We will require all of our guests to comply with any local masking, social distancing, testing, and other safety protocols required by any hotels, transportation, restaurants, and venues that we work with, and where trip organizers deem it necessary to protect the health of all participants. Whenever possible we will give you ample advance notice so that we are all fully prepared, but we also ask that everyone maintain flexibility and concern for the welfare of the group whenever we may need to make adjustments while en route. Such is the world we live in now, and we’re all getting pretty good at mid-course correction!

And what happens if global conditions change or a trip begins to look unwise or unsafe? Well, we’ll do what we’ve been doing for the last 2 years – we pivot. If safety becomes a concern with any of our trips, we will change what we have the power to change, and if that’s not possible, we’ll look to re-schedule or offer refunds. Please see our updated cancellation/refund policy under the "Fine Print" section further down this page.


Saturday, June 11, 2022: Portland, ME (optional): For those who wish to explore the wonderful city of Portland, we will be offering a pre-trip add-on night at our 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.

Sunday, June 12th: The trip officially begins. We gather and board our chartered motor coach in Portland to head up the coast for a brief lunch stop in Freeport where you can also visit the flagship LL Bean store and outlet (It's the law, everyone who visits Maine must stop at LL Bean). We'll continue to Boothbay Harbor - one of Maine's most charming harbor towns - where, if time permits, we'll squeeze in a side trip to the Coastal Maine Botanical Gardens. After exploring Boothbay’s many delicious dinner options, 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 13th: We board the morning ferry in Port Clyde for a cruise across Muscongus Bay. For those interested in the Wyeth family of painters and the rich history of the area, we’ll offer an optional local tour (on a lobster boat!) to see some of the iconic Wyeth landscapes, then catch the afternoon ferry over to Monhegan. It’s a short one-hour ride across the bay, 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, our first night of music, then retire to the sounds of ocean breezes and crashing surf.

Tuesday, June 14th, Wednesday, June 15th, and Thursday, June 16th: 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 and depending on the weather, opportunities abound for such activities as seal and/or puffin watching, lighthouse tours, sea kayaking, visiting galleries and studios of local artists, 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 presentation from a fourth generation Monhegan lobsterman with a live lobster hypnotism, and a chance to examine the island’s archeological finds of a local collector.

Lunch is on your own each day, 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. This year, your trip price includes a wonderful dinner each night that we are at the Monhegan House, and a chance to get to know your fellow travelers over a glass or three of wine.

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. Bring your watercolors, yarncraft, journals, and whatever creative supplies you need to enjoy a chance to really delve into creativity.

Ellis and the other artists will be collaborating on fireside (or front porch, depending on the weather) chats about the songwriting process, the life of the artist, and any number of other topics that inspire them, as well as sketching sessions and informal picking parties on the front porch 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 for those who wish to participate. 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 17th: After a last breakfast at the Monhegan House and a final morning on the island, we’ll head back across the bay, get collected by our bus and whisked off to the stunning Pemaquid Lighthouse State Park, where we'll have a picnic lunch before heading south, 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 18th: Trip participants head home.


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.

VANCE GILBERT: Vance Gilbert defies stereotypes. It’s little wonder then that he also exceeds expectations. In this case, those two qualities go hand in hand. “I’m black, I sing, I play an acoustic guitar, and I don’t play the blues,” Gilbert insists. That may be a broad statement, but it rings with truth.What he does do is make memorable music, as evidenced by the 13 albums he’s released so far, as well as the mark he’s made on the folk and acoustic music scenes in general. Over the course of a prolific career that extends back to the early ’90s, he’s recorded with his good friend Ellis Paul and shared stages worldwide with Aretha Franklin, Shawn Colvin, Arlo Guthrie, the Milk Carton Kids, George Carlin (150+ shows), Anita Baker, the Subdudes, Paul Reiser and any number of others.

MOLLY VENTER: Molly Venter is perhaps most widely known for her work in the beloved Americana/Folk trio Red Molly and her participation on this trip as a solo performer gives us an opportunity to fully enjoy the breadth and depth of her artistry. Her calling card is her powerful, nuanced voice, swinging from a silky whisper to a bluesy shout in a single breath. American Songwriter magazine writes “Few singers turn first time listeners into eternal fanatics as effortlessly as Molly Venter.” Her knack for shedding lyrical light on emotional darkness has earned her placements at Rocky Mountain Folks Fest & Kerrville Folks Fest songwriting competitions. Molly’s latest project, Goodnight Moonshine – a duo album with singer-basist-guitarist Eben Pariser of Brooklyn quartet Roosevelt Dime – recently landed at #12 on the Folk Charts and was the Recommended Hot Pick for Euro-Americana charts.


Before purchasing your space, there a few things to make note of regarding Monhegan Island:
  • There are no passenger 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. We will have a golf cart at our disposal, so we’ll be able to ferry you up the hill to the lighthouse or up to the brewpub, if hills are not your cup of tea. There are no elevators anywhere on the island, 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 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 is hardly ever a wait. We always have the hotel packed full, and it all works beautifully.

ECONOMY SINGLE BED ROOM: Special Early Bird Pricing $2289 per person. 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. AS OF MARCH 1, THESE ROOMS ARE SOLD OUT

DOUBLE OCCUPANCY ROOMS: 2989 per person. A lovely second or third floor room with Queen or double bed and shared bath. 

DELUXE COUPLE,  $3489 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.

DELUXE COUPLE,  $3389 per person - Fish and Maine apartment: A lovely apartment suite (also with private bath and kitchen!) about 120 yards from Monhegan House. Your breakfast and dinner are included at Monhegan House. Daily housekeeping is not included with these apartments, but trash is picked up daily and supplies replenished. The remaining apartments available at Fish and Maine have Queen beds, and must be booked as double occupancy.

FULL SOLO SUPPLEMENT, $750 per person: For single travelers who wish to have their own hotel room in Portland, Boothbay and Monhegan.

PARTIAL SOLO SUPPLEMENT, $300 per person: For those solo travelers who wish to have their own hotel room in Portland and Boothbay, but are purchasing the Economy Single Bed at Monhegan House.


Pay in full for maximum savings! 2% discount . It makes our life much easier if trips are paid in full, and we pass the savings in time and bookkeeping on to you.

 Paid in Full Economy Single, Per Person: SOLD OUT

 Paid in Full Double Occupancy, Per Person: $2929.22

Paid in Full Deluxe Monhegan House Suite, Per Person: $3419.22

 Paid in Full Deluxe Fish and Maine Apartment, Per Person: $3321.22

- OR-

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:

Economy Single Balance, Per Person: SOLD OUT

Regular Double Occupancy Balance, Per Person: $2689.00

Deluxe Monhegan House Suite Balance, Per Person: $3189.00

Deluxe Fish and Maine Apartment Balance, Per Person: $3139.00

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

FULL SOLO SUPPLEMENT, $750 per person: For single travelers who wish to have their own hotel room in Portland, Boothbay and Monhegan.

PARTIAL SOLO SUPPLEMENT, $300 per person: For those solo travelers who wish to have their own hotel room in Portland and Boothbay, but are purchasing the Economy Single Bed at Monhegan House.

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

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. We hate to see anyone have to cancel a trip within our 90 day window and lose their investment, which is why we stress the importance of trip insurance. We also recognize that we all operate with different litmus test for what feels safe these days, and should you find yourself in a situation where the trip is still happening, but you make a personal decision not to participate, we may not be able to find a buyer for your space and would not be able to issue a refund. Really, truly, we think travel insurance 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 well for all: the person needing to cancel recovers most, if not all, of their investment, and a person who might have been on a waiting list gets to go on the trip - however, there are no guarantees.

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 always be recovered if a trip needs to be postponed or cancelled due to health and safety concerns. Given that the world continues to be filled with unknowns, we are proceeding ahead with guarded 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. Please read through our cancellation policy carefully and feel free to reach out to us with any questions or concerns.

Pandemic-specific cancellation policy: In the event that Covid-19 or other concerns cause Roots on the Rails to postpone or cancel a trip, guests will have 30 days to inform us of their choice of one of these three options:
  • a) Holding their reservation at the price they paid and therefore gaining priority access to claiming a spot on the re-scheduled trip within 30 days of our announcement of the new trip dates.
  • b) Transferring any payments to another trip, pending availability.
  • c) If the re-scheduled trip is not viable for a guest, and they wish to request a refund, such requests must be made within 30 days of the announcement of re-scheduled trip dates.
General (non-pandemic-related) 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.