Advertisement in the Brunswick Telegraph, June 20, 1862

“The house has been erected during the present season, and everything about it will be new and in the best style and taste. It has a commanding position, the most elevated on the point, and affords a magnificent view of the ocean, the headlands about the mouths of the Kennebec and New Meadows rivers, and a wide stretch also of the latter river.” -Daniel W. Simpson, Proprietor

Excerpt from a testimonial that accompanied the ad:

“The drive is a pleasant ride for an afternoon, from Brunswick, say for example, leave at 2 or 3 and return by 8 or 9 P.M. At times Cundy’s Harbor is alive with fishermen. And fresh fish can always be obtained there.”

From Wikipedia:

“Built in 1862, it is believed to be the oldest purpose-built summer resort hotel in the state. It was listed on the National Register of Historic Places in 1985.”

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The Union Hotel in Cundy’s Harbor opened its doors for the first time on the Fourth of July in 1862. Cundy’s Harbor had blossomed in the previous ten years into a full-fledged fishing village. In 1861-62, Daniel Simpson married Mary Watson and moved from Brunswick to Cundy’s Harbor and purchased from his parents-in-law for $25 the hill on which he proposed to build a hotel. Thus, at the age of 25, Daniel became a member of a family of fishermen, merchants and traders and determined to try his hand at the hotel business.

The original structure consisted of a large square building that had a kitchen, dining room and parlor on the first floor and four guest rooms upstairs. The building was situated facing south to provide sweeping views of the water and to take advantage of natural heating and light. Two of the bedrooms have access to a rooftop addition that offers breathtaking views of the New Meadows River and the harbor. Most cupolas are square and primarily installed for ventilation, but the structure that crowns the Union Hotel/Captain’s Watch was built with headroom and 8 sides, indicating that its primary use is for viewing. This rare octagonal windowed room is technically called a belvedere (from the French word meaning “beautiful view”).

The original building also included an “ell” that served as a tavern, the second floor of which was divided into smaller guest rooms. Over the years it was said that these rooms had a turnover rate that was more brisk than the stately rooms of the hotel itself.

Advertisements and complementary articles appeared in the Brunswick Telegraph newspaper, but the timing was bad. Despite the beauty of the house and location, and the abundance of finest local produce, the Civil War economy must have been the major factor that brought the hotel to failure in 1863. A Sheriff’s sale was held at the Municipal Courtroom in Brunswick on July 6, 1863, just a year after the gallant opening. Robert Watson, Daniel Simpson’s father-in-law, covered outstanding debts to clear the bankruptcy. It appears that Daniel and Mary retained ownership of the now defunct hotel, which was used as a church and a school until 1874, when it was sold for $800 as seen in a deed in the Cumberland Country Registry.

In 1867 the hotel was taken over by James Jewell who operated it until 1885. Captain E.D. and Laura Percy later operated it as the Cliff House and Percy House until 1905. From that time the hotel remained vacant until the 1920’s when it was used to sell shore dinners.

By the end of WWII local people described the old hotel as badly deteriorated and vacant most of the time. The house/hotel was unused from about 1938 to 1946 when it was purchased by Richard Hatch who had extensive remodeling done and used it as a residence. He added the single-story ell off the north side which can still be seen from the road.

In the second half of the 20th century the hotel was owned by a succession of people, each of whom made changes and improvements. The original building had rough unpainted siding and covered porches on both the first and second stories, though these were later removed. At some point the building was painted white and it remains white today. Shutters were added at one time but they were later removed. These changes and a cast of new owners brought a series of new names to the hotel, now often called a bed-and-breakfast, including The Inn on the Hill, the Cupola House B&B, and The Captain’s Watch.

The current owner is Donna Dillman who runs the B&B on a limited basis, catering to guests who are specifically interested in visiting Harpswell and the surrounding area.

Condensed from A History of the Union Hotel, Harpswell, Maine by Sally W. Rand, May, 1985

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Connection to Harpswell Heritage Land Trust

If you look to the right over your shoulder as you drive into the village of Cundy’s Harbor, the Captain’s Watch towers as the highest structure in town, stately in its white clapboard. Imagine, for a moment, that a new owner covered the historic facade with aluminum siding and removed the stately cupola from the roof. What a sad day that would be.

Fortunately for all of us, Ms. Dillman has taken measures to ensure such a thing will never happen. Working with the Land Trust, an easement was created that requires that any future use of the building proceeds without any changes to the facade that can be viewed from the road. Staff from the Land Trust work with all easement holders annually to confirm that all parties adhere to the stipulations mutually agreed upon when any easement is created.

The wings/ells are not a part of the HHLT easement, nor the west and north sides because they have had significant modifications over the years. Maintaining the south and east sides are the critical elements of the easement and those windows and dimensions have not been altered.

From Ms. Dillman, the current owner: “Keeping this noble building safe from the elements is a constant challenge, but I am proud to be a part of the long progression of owners as caregivers, actually myself being the longest owner/resident of any who have been a part of the structure’s history.”