This drawing by a young architect working for Wheelwright & Haven depicts the Islesboro Inn, one of the finest hotels catering to the carriage trade around the turn of the twentieth century. During this period, developers were buying up tracts of land along the Maine coast, opening resort hotels with amenities like golf courses, carriage roads, and yacht moorings, and selling adjacent cottage lots to their guests. The Islesboro Inn was developed in 1889–1990 by the Philadelphia-based Islesboro Land and Improvement Company, which owned approximately 1,500 acres of shore frontage on this beautiful Maine island.
The design combines Tudor Revival with Shingle Style features set upon a massive stone foundation, with a piazza and pillared porch overlooking the bay. The drawing depicts guests being greeted by staff at the entrance, surveying the view through a telescope, and walking a dog—suggesting an atmosphere of relaxation and discreet luxury. The reception rooms, with their carved oak furniture, framed etchings, and oriental rugs, resembled the furnishings of a private home.
So successful was the inn in its inaugural year, with its rooms fully booked, that it was expanded the following year, again in the late 1890s, and once more in 1913. At the close of the 1915 season, the hotel was destroyed by fire. A new company was formed to rebuild it, resulting in the second Islesboro Inn, a Colonial Revival structure erected on the same foundation, which opened in 1917.
Written by Earle G. Shettleworth, Jr., Maine State Historian
Earle Shettleworth is the recipient of Historic New England’s 2024 Preservation Leadership Award. This article originally appeared in the Fall 2006 issue of Historic New England magazine. Check the blog monthly for new posts in our Collection Stories series.
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