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 We've reproduced this historical document in full color and are offering it for sale (unframed) for $50.00 plus tax in the Museum.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.

Cottage Map.jpg

Aesthetics of the Everyday—Home Movies from Northeast Historic Film

 Karan Sheldon, co-founder, and Michael Hutcherson, board president and Islesboro resident

August 9.  Screening and Discussion, 7:30pm

"There is an old idea that amateur art is the purest, because it is made without consideration of money or fame. Here is the proof—vivid slices of real life as rich and rewarding as any gallery of Old Masters, rescued from obscurity through the extraordinary efforts of Northeast Historic Film. The essays in this volume, written in plain language, provide fresh insight into this still underappreciated art form. Like great paintings, the films themselves are impossible to forget.”  Phillip Prodger, Head of Photographs, National Portrait Gallery, London

For a tiny taste, go to


The Talent Show Nears!!!

Remember, the Island Talent Show will be held at the Historical Society on Wednesday June 21 from 7-9pm. The pre-school will again be selling refreshments before the doors open at 6:30, and at intermission. Admission is $5 to cheer on the most talented folks on Islesboro!

If you can recite "The Jabberwock" from memory, sing "Hey Jude" while juggling chain saws, or have some other talent and want to perform, please contact Amanda at This year we're going to have rehearsals on both Monday and Tuesday evenings (June 19 and 20) from 6-8pm - you only need to come to one rehearsal.

See you there!

JOB POSTING - Administrative Assistant



Hours:  Year round part time, with 8-10 hours per week early May through late September at Islesboro Historical Society office; flex hours during off season at home.

Description:  This position involves handling correspondence, record keeping for IHS art shows and publication sales, processing checks under the supervision of the IHS Treasurer, telephone answering, and other related responsibilities as may be assigned by the IHS President, Finance Committee, or Board of Directors. IHS provides orientation, support and resources for the position.


  • Good organizational skills

  • Computer literacy

  • Willingness to learn

  • Creativity and flexibility in dealing with new situations

  • Responsibility, honesty

  • Strong interpersonal skills

  • Reliable transportation


  • Microsoft Office skills including Word and Excel

  • Quick Books familiarity

To Apply:

  • Mail resume and supporting materials to:


PO Box 301

Islesboro, ME 04848

               This position is open from April 22, 2017 until filled.

 For further information – Email

Or call one of the following – IHS – 734-665

                                                     Patrick O’Bannon, President – 513-300-1511

                                                     Doug Welldon, Finance Committee – 734-6655

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.