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Trailing Yew

Trailing Yew, located on Monhegan Island, Maine, offers a total of 26 accommodations available for reservation between the months of May to October. During the business’s season of operation, the Trailing Yew sees a relatively high number of repeat guests and those coming to the island for the first time. On the property’s premises, there are five buildings where the 26 different rooms are split between. Three of the rooms have private ensuite bathrooms, while the rest share with others. Each building has a common area and a porch. A yard is located between all the facilities where activities such as cornhole, Jenga, and frisbee are available. Also provided to guests is breakfast, which is served in the dining room, and coffee is delivered to patrons’ rooms if desired.


Situated on Monhegan Island, Maine, is Trailing Yew, a local bed and breakfast. Monhegan Island is located about 12 miles off the coast of the United States. In total, the island is about a mile and a quarter long and less than a mile wide, which the owner says results in the town being “super tiny.” The Trailing Yew is one of the few companies and homes that are located on a third of the island, while the rest of the island remains undeveloped. Marian, the owner, says that around her business, there are a few rental properties, but in total, only about “50 people live [on the island] year-round.” The property offers 26 accommodations; all split between three houses and two relatively smaller buildings. The Yew Building, The Seagull, The Annex, The Cabin, and the Studios are the names of the five buildings. Each of these is described by Marian as “beautiful old houses,” with all having hardwood floors and old-fashioned floral wallpaper. A guest said in a review, “A beautiful lodging on Monhegan. It is very rustic, and we loved that. We loved the 19th-century feel.” All the buildings are situated to encompass the main lawn on the premises, where a view of the ocean can be seen. Cornhole, Jenga, and frisbee are a few examples of activities occupants can participate in in the yard. Other outdoor features include picnic tables, multiple flower gardens, and a vegetable garden.

Out of the 26 rooms, only 3 have private ensuite bathrooms, while the rest share bathrooms. The three rooms with private bathrooms are the most popular among visitors to the property. The rooms on the second floor of The Seagull are also popular due to the better water views they offer compared to the other accommodations. Each room has different size beds, the largest being queen-sized. Other amenities located in some of the units include a small sitting area, side tables, and a bureau. Regardless of the room, a visitor has access to the business’s WiFi.

Each building has some type of common room; additionally, each one has a porch attached that has views of the ocean. Guests are able to access any common area on the property, regardless of the building they are staying in. Breakfast is included in a stay at the Trailing Yew, served between 7:30 and 9:00 AM in the main dining room, but they can choose to sit at picnic tables if they prefer to eat outside. Items that may be served include doughnuts, muffins, fruit, yogurt, granola, scrambled eggs, and quiche. Accommodations for certain types of dietary restrictions are able to be made; before arriving at the property, the establishment asks guests if they have any of these restrictions in order to prepare for these restrictions. Also available to patrons is a bake shop that is open from 9:00 AM to 2:00 PM. Visitors are able to buy baked goods, such as brownies, cookies, cakes, bagels, and cupcakes. The shop also acts as a café, serving meals such as avocado toast, lox toast, peanut noodles, and salads. Everything they serve is a “mix of everything we love to eat,” says the owner.


Marian, the owner of Trailing Yew, remarks that repeat guests are a big part of their business, with usually sixty percent of guests being repeat. Some patrons have been coming to the property since they were little kids and have started to bring their own children. Marian talks of how she has enjoyed being able to see the timeline of families that continually come to the establishment since she has been at the Trailing Yew since the 1980s, and that this “makes me smile.” One review left by a past patron said, “I stayed here this past week, and everything was excellent. The staff are all super nice and accommodating, and the building is in a great location to see the views of the ocean.”

The goal of the property is to provide a place where visitors can come and “feel relaxed and comfortable” so that they want to keep coming back to stay at the Trailing Yew, says Marian. One way she tries to create this atmosphere is by listening to what her visitors want and need and “stopping and talking with them” during their stay. The typical demographic of guests varies anywhere from families to artists, and the establishment even receives a high amount of people coming to bird watch, depending on the time of year. Due to this, there is relatively high interaction between patrons and staff. This level of interaction is what Marian says is unique for the business and that it tends to leave them to “become friends with our guests.”

Monhegan Island is located off the coast of the main portion of the state of Maine. Although the land area of the island is relatively small, there are still trails people can walk that will reach about 17 miles long since they “crisscross the island,” remarks the owner. These trails are a common draw for tourists since they lead to views of the oceans and what the owner describes as “cliffs that are located on the backside of the island.” One local attraction includes the Mohegan Historical and Cultural Museum, which often hosts events, such as art shows. Events hosted on the business include weddings, as well as catering events for other places on the island. The catering the property offers is one thing they are known for within the area. If guests are looking to eat out, Marian recommends they try Bait Bag; Novelty, which serves pizza; the Fish Market; The Monhegan House; and the Island Inn.

Policies for the Trailing Yew include no smoking in any of the buildings and that pets are only permitted in certain rooms and need to be arranged prior to arrival. Quiet time starts every night at 9:00; however, the owner remarks they usually never have an issue enforcing this. In terms of operation, the Trailing Yew is only open seasonally for about six months of the year, typically from May to October. The typical busiest time for the business is between August and September.


The property where the Trailing Yew is located was originally settled in 1850 by Siman and Elizabeth Humphrey. Later in 1892, the business was purchased by the couple’s son, William S. Humphrey, and his family. Eventually, the establishment was again purchased in 1926 by Josephine Davis Day, and she became the first person to start renting out rooms on the property. During Josephine’s ownership, she added other buildings to the premises, including the Annex, and inherited The Seagull cottage. Josephine continued to operate the business until 1996 when she passed away at 99 years old. The current website pays homage to Josephine’s ownership, quoting her statement, “When you run a place, you’ve got to treat your help like friends. They are my friends.”

The current owner, Marian, started working at the business in 1980, during Josephine’s ownership. When Marian first started working at the Trailing Yew, she initially intended to only stay for a year, but she ended up never leaving because she loved working for Josephine and being at the Trailing Yew. Eventually, she purchased the company in 2009, making her the second owner of the business. Marian’s favorite part of working at the property is meeting “all of the different people” that come to the establishment. She continues to remark that she has, in essence, had the opportunity to “watch people grow up” since they continually come back to stay at the Trailing Yew, and some have even started to bring their own children.

Changes that Marian has made to the Trailing Yew include adding electricity to all of the buildings, upgrading furniture and linens, and changing the meals that were previously served. One hope the owner has for the future includes one day adding more private bathrooms to the rooms. However, she mentions they “try to change it as little as possible; people love it the way it is.” Another plan is to do an event to celebrate the establishment’s 100th year of operation.

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8 Lobster Cove Road
Monhegan Island, Maine 04852
United States


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Josephine Davis Day

4.8 (39 Reviews)
4.8/5 39 Reviews
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