Roots Rails & Rambles Roots Rails & Rambles

Monhegan, Sept. & Oct. 2024




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, with many of our repeat guests counting this trip as their annual opportunity to slow down, breathe deeply and be surrounded by music, stunning scenery, and a deliciously uncluttered agenda.

Days on Monhegan can be as energetic or as laid back as suits your style. There are twelve miles of hiking trails ranging from gentle strolls to hair-raising scrambles along rocky cliffs, art galleries and studios that welcome visitors, yoga classes, massage, and other self-care activities available, a great local brewpub just a brief stroll away from our front door and the world’s best front porch, replete with many rocking chairs, perfect for reading, chatting, knitting, napping or jamming with your fellow travelers. 

In the evenings, following a delicious dinner, we 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.

Seth Glier, Vance Gilbert, & Crys Matthews are coming together on this trip for a unique collaboration of songs, stories, and creativity. Seth Glier is a Grammy nominated musician, 5 time independent music award winner, and has shared the stage with a diverse list of artists ranging from the likes of Ronnie Spector, Ani Difranco, to Glenn Campbell. 30 years into Vance Gilbert’s career, the songwriter’s influence can be felt all over the contemporary folk and americana realm as he has helped pave the way for many of the BIPOC artists who have followed. Crys Matthews is already being hailed as “the Next Woody Guthrie” and is among the brightest starts of the new generation of social justice music-makers. All three artists have come together to unravel and reweave the musical threads of folk.

For those of you who have joined us before for this trip, we’re changing it up in a few exciting ways this year! We’ll be starting and ending the trip in Boston, MA – easy to get to and from and a great place to do some historic sightseeing. We’ll also be taking Amtrak’s Downeaster between Boston and Brunswick, ME – a delightful ride through the scenic marsh land along the Atlantic coast. And we’re going at the tail end of the season, when the weather is still spectacular and the island is a little less crowded. The water may even be warm enough for a dip without risking hypothermia!


Saturday, Sept. 28: Boston, MA. The group gathers at our Boston hotel for brief introductions and trip registration before we head out for a concert at one of Boston’s reknowned music venues. For anyone wishing to arrive early and do some independent exploring, we will have rooms available at our group rate.

Sunday, Sept. 29: The trip officially begins! We gather and board Amtrak’s Downeaster at North Station, then head up the coast to Brunswick, ME where we’ll be met by our chartered motorcoach to be whisked off to lovely Boothbay Harbor one of Maine's most charming harbor towns, where we'll enjoy a concert with all three artists and spend the night at our harborside hotel.

Monday, Sept. 30: This morning, those who are interested can make a visit to the Botanical Gardens then on our way to catch the ferry we’ll make a lunch stop in Rockland. 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, Wednesday, Thursday Oct. 1-3: 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 on the island is on your own, with delicious options scattered around the village. We dine together at Monhegan House every evening (included in your trip price) before our nightly music program. The food is amazing, much of it sourced from the Monhegan House gardens. 

The artists will be collaborating on some informal workshops/gatherings during the days – it’s a great chance to spend some time with them delving deeper into their interests – musical and otherwise. We’ll also be building in opportunities for Open Mics (without microphones), and informal song circles out on the porch or under the apple trees. Bring your instruments if you play!

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 (included, with alternatives for non-lobster eaters), with lobsters pulled right from the Monhegan waters.

Friday, Oct. 4: After a last breakfast at the Monhegan House we’ll hop back on the ferry and head back to the mainland where our bus will pick us up and get us to the train for our ride back to Boston. We’ll host a final get together at our hotel that evening.

Saturday, Oct. 5: 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 all have shared restroom and shower facilities. At the Boston and Boothbay Harbor hotels all rooms 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. 

DOUBLE OCCUPANCY QUEEN: $3489 per person.
A lovely  shared second or third third floor room with Queen bed and shared bath. 

DELUXE COUPLE, DOUBLE OCCUPANCY: $3989 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.  Only 1 of these left!



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.

Single Bed/Solo occupancy PAY IN FULL: $3125.22

Double Occupancy PAY IN FULL: $3223.22 per person

Deluxe Couple PAY IN FULL: $3909.22 per person

Single person solo supplement: $900


If you'd rather pay a deposit to hold your space(s): $500.00 per person deposit

THEN, Within 30 days of deposit, settle your remaining balance or set up a convenient interest-free monthly credit card draw by contacting Sarah at or 802-258-1397.

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. Liability release signature required.


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 current songwriting work is centered around themes of reuniting humans with the natural environment and reimagining our relationships with the planet. Lest you think Seth is in a constant state of somber grappling with the weighty issues of the universe, be assured that he is one of the world’s funniest people and an utter delight to travel with!

VANCE GILBERT: With a thirty year/thirteen album career under his belt, Vance’s influence all over the contemporary folk and Americana realm is immeasurable. His new album, "The Mother Of Trouble” (featuring Lori McKenna on background vocals, Joey Landreth on guitars, and Americana-Roots master mandolinist Joe K. Walsh). With 4 bullies, 4 deaths (3 of them murders), 3 moms, 2 accidents, 2 Black people, 2 dogs, 1 dog ball, 1 gay kid, and 1 missed flight thanks to gas station sushi, this album benefits from the gifts of time and experience honing songwriting skills that put this most vital of acoustic storytellers at the top of the game. In the very first week of the pandemic in 2020 Vance launched Vance’s Monday Night Acoustic Pajama Party on YouTube - a live, themed, weekly 90 minute mixed bag of originals and cover tunes to a rotating following of about 200 folks. 10 to 20% of his weekly tip jar is donated to a local 501(c)3 of his choice. At the time of this writing, having done 155 of these shows has become newsworthy in itself.

CRYS MATTHEWS: Already being hailed as “the next Woody Guthrie,” Crys Matthews is among the brightest stars of the new generation of social justice music-makers. A powerful lyricist whose songs of compassionate dissent reflect her lived experience as what she lightheartedly calls "the poster-child for intersectionality," Justin Hiltner of Bluegrass Situation called Matthews’s gift "a reminder of what beauty can occur when we bridge those divides." She is made for these times and, with the release of her new, hope-fueled, love-filled social justice album Changemakers, Matthews hopes to take her place alongside some of her heroes in the world of social-justice music like Sweet Honey in the Rock and Holly Near. Of Matthews, ASCAP VP & Creative Director Eric Philbrook says, “By wrapping honest emotions around her socially conscious messages and dynamically delivering them with a warm heart and a strong voice, she lifts our spirits just when we need it most in these troubled times.

Since the advent of Covid-19, and its impact upon travel, we feel purchasing travel insurance has gone from wise precaution to fiscal necessity. Going forward, we are strongly suggesting that all patrons carry trip insurance that provides, at a minimum, coverage for the following:
  • Cancellation for Covid-19 illness
  • Trip Cancellation
  • Trip Interruption
  • Cancel for Medical Reasons
  • Medical Coverage for Covid-19 (often included under Emergency Medical Care)
  • Emergency medical care
  • Medical Evacuation
You may purchase travel insurance through any company you choose, and we advise checking the coverage on the credit card you used to secure your booking with us -- often there are travel protections built in to your user agreement. If you're unclear on where to begin your travel insurance search,  we can suggest looking at products such as AXA USA Assistance Silver or Nationwide Essential  which provide robust coverage for all those items at a very fair price. Both of those products (and many more) can be purchased through our affiliate, Squaremouth. Because travel insurance is such a highly personalized product, when you click on the link and are directed to the Squaremouth landing page and the "Compare and Buy Travel Insurance" calculator, you’ll have to enter your own demographic information – age, state of residence etc. -- after which you'll be presented with a number of options to consider. Among them will be the AXA and the Nationwide products. You are certainly not limited to those two products – we are merely outlining the elements of coverage that we are strongly suggesting going forward and a convenient way to access them. If you purchase the policy through that link to Squaremouth it does not cost you anything more than purchasing the product directly from the vendor, but we do receive a small commission.


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. We 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.

Cancellation policy: Deposits, whether paid separately or as part of a full payment up front, are non-refundable. Outside of deposit and credit card fees, full refund will be given up until 90 days prior to start of trip. 50% refund 60-89 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.

Roots, Rails, and Rambles 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 Roots, Rails, and Rambles acts only as agent. Roots, Rails, and Rambles 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. We reserve the right to cancel any tour prior to departure, in which case payment will be refunded without further obligation on our part. Roots, Rails, and Rambles shall not be responsible for any injury to person (whether or not resulting in death) or damage to property.

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. Roots, Rails, and Rambles reserves the right to cancel or withdraw any person as a member of the tour at any time. Roots, Rails, and Rambles reserves the right to refuse service to anyone whom it considers incompatible with the best interests of its services or its guests.