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Spring 2024 Newsletter

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December 2023

Just in time for New Year’s! We are very excited to announce that we have posted our island genealogies on our website: for your research and browsing pleasure. A huge thank you to Catherine Demchur-Merry for working out the kinks in this process - which was not easy!

There are two databases, accessed from the "Island Genealogy" button on the home page. "Summer Families" is largely devoted to those families that built cottages in Dark Harbor. "Year Round Families" includes (obviously) families who resided on the island year round. There are, however, plenty of folks who might be considered summer families that are included in the year round database - including summer residents of Hewes Point, Ryder's Cove, and other areas. If you can't find who you're looking for in one database, try the other. The user interface is not the slickest we've ever seen, but once you click on a name you can then click on links for the individual's parents and siblings. It should let you roam pretty far down into the rabbit hole! We cannot promise that these records are 100 percent complete or accurate, but we've tried to get them as close to that goal as possible. The starting points for the Year Round database were the family histories in the 1893 and 1983 town histories. We tried to verify all that information with primary source documents (birth, marriage, death, and census records) available through We followed the same process for the Summer Families database - starting with Shettleworth's "Summer Cottages of Islesboro."

Because of privacy concerns, records are generally less available for the period after 1950. As a result, the holes in the data get larger as one gets closer to the present. That's one reason we've put a "Family Group Sheet" on the website, so that you can correct our mistakes, add additional family members, and generally help us make this more complete and more accurate.

Please let us know if you have questions or problems. Enjoy!

Spring 2023 Newsletter

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June 24, 2022


Dear Friends of the Historical Society:

The Historical Society is looking for volunteers for the museum. This is a great time to meet people, learn the history of the island, and participate in an art show.

An important aspect of the Historical Society is the museum located on the second floor of the building. The museum is open from July 2nd to August 24th; Saturday through Wednesday afternoons from 12:30 to 4:30 pm. Volunteers sign up for one of two 2-hour shifts at the museum to be available to answer questions from visitors. When time allows, you are welcome to browse the collection and familiarize yourself with the history of the island. Training of docents is provided prior to the start of the season.

July 31, 2017
It's Here - Islesboro Cottages Map!

The Historical Society is pleased to be able to offer reproductions of the ca. 1925 Islesboro Land & Improvement Company's "Map of Dark Harbor." Long out of print, the map depicts the southern end of the island and shows the location and owner's name of many of the Dark Harbor Colony's cottages. We've reproduced this historical document in full color and are offering it for sale (unframed) for $50.00 plus tax in the Museum. We have a limited number available, so be sure to drop by and pick up your copy.

image of cottages map

December 21, 2016
The Islesboro Land & Improvement Company

One of the most important changes to take place on Islesboro in this period was the development of the Dark Harbor summer colony. This development is closely tied to the activities of the Islesboro Land & Improvement Company, which purchased large tracts of land in the 1880s, subdivided the land into lots, and offered those lots for sale to “rusticators” and summer cottagers. The Land & Improvement Company did not represent the first effort to bring summer visitors and residents to Islesboro. Shortly after the Civil War, hotels at Ryder’s Cove and Hewes Point began to cater to vacationers from Bangor, who arrived by steamer at the east side landings. About 1882, Benjamin Ryder and William R. Coombs, owners of most of the shoreline at Ryder’s Cove, began to subdivide their property and sell off building lots for as little as $25. Sewell Fletcher began to do the same thing at Hewes Point at about the same time. And at the far southern end of the island, Jeffrey Brackett, a wealthy young Bostonian, purchased Job’s and Middle Island and about 150 acres at the southern tip of the island in 1882 for a summer estate.

Clearly, real estate development was in the air on Islesboro by the early 1880s, when Boston real estate broker James Murray Howe discovered North Haven and began development of a summer colony on that island. In 1884 Howe visited Islesboro, decided the island was ripe for its own summer colony, and began casting about for investors. Howe promoted Islesboro to James D. Winsor, the Boston-born owner of a Philadelphia-based steamship company, who toured the island with Howe in the spring of 1885. Winsor organized the Islesboro Land & Improvement Company, whose investors were mostly fellow wealthy Philadelphians, and began buying land on the island in 1888. In August 1889, Winsor turned over 36 separate parcels, totaling well over one thousand acres, to the Land & Improvement Company, who hired surveyors to map and subdivide the parcels into building lots and began offering those lots for sale. To facilitate sales of building lots, and to provide for the budding summer community, the Land & Improvement Company spent $175,000 to build the Islesboro Inn, a 39-room hotel with its own steamship dock, perched above the southern shore of Dark Harbor pool.

This part of the story is fairly well known, but the Land & Improvement Company’s interests extended well beyond Dark Harbor to include parcels across the islands that featured water access and stunning views. Winsor purchased significant tracts of land on the west side of the Meadow Pond, on Coombs Bluff, overlooking Ryder’s Cove, on Keller Point, and on 700 Acre Island. Some of these parcels were developed by summer residents. For example, George W.C. Drexel a Philadelphia newspaper publisher and banker, bought over 150 acres on Coombs Bluff in 1902 from the Land & Improvement Company and hired the Boston-based architectural firm of Peabody & Stearns to design his cottage, “Gripsholm,” which was completed in 1904. At Keller Point, Louise N. Grace, the daughter of one-time New York mayor and founder of the W.R. Grace shipping line, William Grace, purchased nearly 135 acres in 1918 from the Land & Improvement Company and hired prominent Philadelphia architect Wilson Eyre to design her cottage.   

Other parcels were purchased simply as investment opportunities. In 1889, for example, when the Land & Improvement Company first began offering land for sale, a Baltimore grain merchant named Blanchard Randall purchased 70 acres north of the former John Gilkey farm, subdivided the tract, and sold off the lots. Several investors in the Land & Improvement Company, notably Philadelphia physician Samuel Dixon, also purchased lots and resold them. A number of tracts remained unsold, and in April 1929 the company voted to accept island resident George W. Dodge’s offer to buy the balance of their unsold property for the bargain price of $5,500. The deal was completed in early October 1929, with Dodge acquiring 19 parcels totaling about 400 acres. The Land & Improvement Company managed to divest themselves of their unsold land two weeks before the stock market crash. At the same time, George W. Dodge acquired property that likely provided him a source of income, through his sales of the various lots and tracts, for the rest of his life.

As we continue to explore old land records we’ll update this story, but for now it’s obvious that Islesboro experienced a wave of development for summer residents in the 1880s and that the Islesboro Land & Improvement Company’s interests extended beyond Dark Harbor to include many portions of the island with water access and sweeping views.    

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