Behind these boys is Ryder’s Hotel, a popular lodging in the early days of tourism on Islesboro. In the building on the right, Benjamin Ryder opened the island’s first boardinghouse for summer residents, the first of whom came from Bangor. Seaside House enjoyed a scenic location on Saturday Cove, now called Ryder’s Cove. As more people discovered the pleasures of vacationing on the island, in 1885 Ryder added the large building with the tower, which accommodated 100 guests, and, later, the white annex across the road. The hotel was known at various times as the Seaside Hotel, The Islesborough, and Johnson-by-the Sea. Guests arrived at the steamship wharf at Ryder’s Cove, which in the 1890s had a millinery and dry goods store, ice cream parlor, post office, livery stables, and private homes. About 1930 two stories of the hotel were removed, and the building became a dance hall.
As Islesboro grew as a summer destination in the 1890s, Bay View House, south of the main steamboat landing, and the Islesboro Inn in Dark Harbor were built, and the first island golf club opened. By 1915, the Islesboro Inn offered 180 rooms for wealthy guests, and Dark Harbor was bordered with many substantial summer homes.