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»

12 Winslow Street

12 Winslow Street, Provincetown (2008), by David W. Dunlap. 
12 Winslow Street, Provincetown (1966). Long Pointer 1966. Courtesy of the Provincetown History Preservation Project.Provincetown High School

April 2013. What a bittersweet moment to be writing about P.H.S. Bitter because, after 164 years, secondary education in town is about to end. Sweet because of the spirit, dignity and pluck shown by the eight young women of the Class of 2013 as they bring this important era to a close.

“I watched my cousins, my sisters and brother graduate from Provincetown High School,” 17-year-old Katie Silva told Mary Ann Bragg of The Cape Cod Times in September 2012. “And I wasn’t about to pass up that opportunity.” In April 2010, the school committee had voted — reluctantly but unanimously — to phase out the school. At the time, Peter P. Grosso (b 1945), the committee chairman and the father of two P.H.S. alumni, said: “I never thought I would see this day. But we’ve just been fighting the numbers. It’s just not going to work.”

12 Winslow Street, Provincetown (2010), by David W. Dunlap.

More pictures and history »

12 Winslow Street

12 Winslow Street, Provincetown High School, by David W. Dunlap (2008).

12 Winslow Street, Provincetown High School, by David W. Dunlap (2008).

“I watched my cousins, my sisters and brother graduate from Provincetown High School,” 17-year-old Katie Silva told Mary Ann Bragg of The Cape Cod Times in 2012. “And I wasn’t about to pass up that opportunity.” She was among the last, however. Two years earlier, the school committee voted, reluctantly but unanimously, to phase out the school after Katie’s class graduated. Peter Grosso, the committee chairman and father of two P.H.S. alumni, said: “I never thought I would see this day. But we’ve just been fighting the numbers. It’s just not going to work.”

12 Winslow Street, gymnasium floor (the teams were called Fishermen), by David W. Dunlap (2010).

12 Winslow Street, gymnasium floor (the teams were called Fishermen), by David W. Dunlap (2010).

The closing was no easy task. For generations, P.H.S. had graduated the sons and daughters of hardscrabble Provincetown with the implicit promise that their lives could be richer and more fulfilling than those of their parents. After the bleak circumstances of coastal Portugal or the Azores or Cape Verde, Provincetown High was a key to the American dream. Classical Revival in style, with a monumental distyle portico topped by a four-foot clock and Lamps of Knowledge, it was also a proud emblem of the year-round town, a place where children were raised to stay.

12 Winslow Street, Ross Moffett murals, by David W. Dunlap (2010).

12 Winslow Street, Ross Moffett murals, by David W. Dunlap (2010).

In 1930, the old high school, which stood virtually on this spot, was consumed by fire. The town acted with extraordinary alacrity to replace it. William Herbert McClean, the Boston architect who designed Provincetown High, specialized in school and library buildings. The contractor was Frank A. Days Jr. The new school was dedicated in September 1931. Its front hall was ornamented by Ross Moffett murals. In 1963-1964, a new gymnasium, vocational school, library, and classroom building opened on what had been part of the Grace Hall parking lot. The year of the school’s peak enrollment was 1967, when the senior class had 53 students.

12 Winslow Street, auditorium, by David W. Dunlap (2013).

12 Winslow Street, auditorium, by David W. Dunlap (2013).

But as property values and taxes soared, old families had little choice but to divide their homes into condos and sell off slices. Buyers weren’t putting down stakes here. The closing of the North Truro Air Force Station in 1994, growing restrictions on fishing, and the dearth of year-round employment were big factors, too, said Dr. Beth Singer, the superintendent of schools. Rising costs and declining enrollment created a self-fulfilling spiral, making it tougher to attract those few students who lived within easy distance. Taxpayers questioned the wisdom of subsidizing secondary education on such a scale.

The plan developed in the early 2000s called for Cape end students to attend Nauset Regional High School in Eastham. The saving grace was that P.H.S., now called the Elmer I. Silva Learning Center in honor of a much-respected principal, would neither be razed nor turned into condos. Instead, the kindergarten through sixth grade classes were moved here from Veterans Memorial to join the seventh and eighth grades, which were already here. The elementary school is “thriving,” Shannon Patrick, a parent and school committee member, told me in 2014.

The Class of 2013 was the final graduating class, by David W. Dunlap (2013).

The Class of 2013 was the final graduating class, by David W. Dunlap (2013).

The Class of 2013 was composed of (back row, from left) Mairead Hadley, Lydia Legnine, Katie Silva, and Bezie Legnine; (front row) Arianna Martinez, Salena Smith, Catie Adams, and Molly Nelson. As their final assignment, they studied the influence of P.H.S. on town life, culminating in an exhibition and commemorative mural. Rather than turn their backs on history, the last graduates embraced it, even as they joined the history books themselves.

24 Winslow Street

24 Winslow Street, Provincetown (2013), by David W. Dunlap. 
246 Commercial Street, Provincetown (2013), by David W. Dunlap.The Dermotage

In 1990, a year after Gov. Michael S. Dukakis appointed him as the first openly gay judge in the history of the Commonwealth of Massachusetts, Dermot Meagher bought this comfortable 1920s house out of foreclosure. He continues to spend time here. Meagher studied not only at Harvard College and Boston College Law School, but at the Provincetown Art Association and Museum, the Fine Arts Work Center and the Castle Hill Center for the Arts in Truro. He retired from the Boston Municipal Court in 2007 and has since published three books: Judge Sentences: Tales From the Bench (2010), Lyons and Tigers and Bears (2012) and Lyons at the Gate: Further Adventures of Judge Joe Lyons (2013), pictured here in the window of the Provincetown Bookshop. Meagher’s artwork is shown at and represented by the Schoolhouse Gallery. More pictures and history»