4 Winslow Street

4 Winslow Street, Provincetown (2008), by David W. Dunlap. 
4 Winslow Street, Provincetown (2010), by David W. Dunlap.Ryder Homestead

The plaque reads: “Circa 1780. Originally located at corner of Commercial and Ryder Streets. Moved here in 1885 to provide space for present Town Hall. During the Civil War, slaves escaping to Canada were fed and given a secret resting place at the homestead.” Rest of the entry to be written.

5 Winslow Street

5 Winslow Street, Provincetown (2009), by David W. Dunlap. 
Howards End Guest House

The Howard in this case is Howard Weiner, the proprietor and manager. His Web site says: “The house, built in 1840, was the residence of the whaling captain Ezra Cook. In the late 1920s through the 1940s, it was the retreat of American composer Cole Porter. In 1946, it was converted into a guest house, and is one of Provincetown’s oldest continuously operating bed-and-breakfasts.” Rest of the entry to be written.

6 Winslow Street

6 Winslow Street, Provincetown (2009), by David W. Dunlap. 
6 Winslow Street, Provincetown (2008), by David W. Dunlap.Chicago House

Why Chicago? That was the hometown of Al Arko and Jerry Newcomer, who opened this guest house in 1960. “Ownership has changed many times, always remaining the Chicago House,” Christopher P. Scales, the current owner, told me in 2010. He added that he had been set to close on the purchase on Tuesday, Sept. 11, 2001. “Instead, the sale was completed on 9/18/2001.” Scales said construction of the house can be documented to the period from 1820 to 1836 but that it may been built earlier in the 19th century. Rest of the entry to be written.

† 12 Winslow Street

12 Winslow Street, Provincetown (ND). Courtesy of the Pilgrim Monument and Provincetown Museum (No. PC 0570.) 
12 Winslow Street, Provincetown (ND). Courtesy of the Pilgrim Monument and Provincetown Museum (No. PC 0571.)High and Grammar School

In 1890, Herman Jennings, wrote in Provincetown or, Odds and Ends From the Tip End: “When the [old] Town Hall was built on High Pole Hill in 1853, the High School was then permanently established and held in that building until the building was burned [in 1877]. The school then was kept in the vestry of the Congregational Church [256-258 Commercial Street] until the present High and Grammar School Building was erected in 1880, the town appropriating $8,000 for the purchase of land and the erection of the building. In this school, the higher branches are taught in connection with several of the foreign languages.” More pictures and history»